S2, E34: It’s Time to Plan Your Winter Travels—Here’s How.

In this week’s episode of Unpacked by AFAR, the three members of AFAR’s mighty destination team tackle all things winter travel.

It’s nearly winter! Which may mean a road trip, an epic overseas ski trip, or months spent cozied up inside. Whatever you want to do—and wherever you’re at in your planning—this week’s episode of Unpacked, has something for you. AFAR’s mighty destination team tackles flight deals, the beauty of traveling between Thanksgiving and Christmas, how to enjoy skiing like a European, and so much more.


Tim Chester, AFAR deputy editor: Around here, people love to dress up in woolly hats and coats in this first sign of a slightly chilly wind.

Mark Ellwood, freelance writer: Oh, it’s cosplay, isn’t it? It’s, it’s cosplay in winter. You go to L.A. and everyone’s like, “Oh, it’s so cold.” And you’re like, “Why—have you got mittens on? What are you—?”

Aislyn Greene, host: I think you lose your edge when you live in a warm place too long. You do kind of, you, you change.

Mark: Listeners, please let us know. People are shaking their fists.

Aislyn: I’m Aislyn Greene, and this is Unpacked, the podcast that unpacks one tricky topic in travel each week. And this week, as you may have guessed by that intro, we’re exploring winter travel and all that entails, from holiday breaks to warm weather vacations to escape the cold.

And maybe it feels a little too early to be talking about this. Near where I live here in Sausalito, California, the pumpkins have just arrived, which I don’t know quite how I feel about. But winter will be here sooner rather than later, and if it’s anything like this summer in travel, it’s probably best to plan ahead.

Also a quick note that this episode also marks the final episode for season two of Unpacked. We’ll be back in your feed in early January 2024. But until then, be sure to check out our other podcast, Travel Tales by AFAR. It’s a series of first-person stories about trips that change us in some way and season four kicks off on Thursday, October 5th. We’ll link to it in our show notes.

But back to winter. For this episode, I spoke with the two editors who make up our mighty destination team here at AFAR, as well as the freelance writer who handles our monthly Where to Go columns. They share tips on surprising winter destinations, the best Christmas markets in the U.S. and abroad, and even how to pack winter gear—or how not to pack it. There are some debates in this one. OK, let’s get to it.

Aislyn: Well, everyone, welcome back to Unpacked. The band is truly back together again. It’s so nice to see your faces in the squares. How’s everyone doing today?

Mark: We’re all dreaming of winter because it’s so hot here in New York when we’re recording, so this is, this is like a mental ice cube that is just cooling me down.

Aislyn: Get right in the headspace. Well, with that in mind, can we all go around and introduce ourselves and say where we are? And if you want to share what beverage you have in hand.

Mark: I’m Mark Elwood. I’m in New York, sweltering on what feels like the only hot day we’ve had in the summer, and I don’t have anything in my hand, but I’m sort of hallucinating a piña colada because it feels like the weather isn’t work weather, but I’m at my desk.

Chloe Arrojado, associate editor: Yeah, yeah, I’m also in New York. Hey, everyone. I’m Chloe. I’m the associate editor of destinations here at AFAR. And as you may hear, I am in my Harlem apartment right now. I actually do have a drink, and it is a mangosteen tea that I have—it’s iced because as Mark said, it is sweltering outside.

Tim: I’m Tim Chester, deputy editor based out in the L.A. area where it’s actually not that hot today. We don’t even have the air con on. So, I’m winning on that front, I suppose. Still in shorts, but yeah.

Aislyn: Nice. And as you know, I’m Aislyn and I’m in Sausalito and it actually feels like winter here. And so I have a hot coffee in my hand. No, no whiskey in there though, as much as I would like that.

Mark: Oh, go on. There’s a little bit in there. Go on.

Aislyn: Maybe a splash, who knows? Um, all right, well, we’re here to talk about winter today. And so, you know, we’re getting those mental ice cubes going. Where are you all at in terms of your, your winter planning?

Tim: Nowhere, personally. Haven’t got that far. I’m—just doing the research for this. I’ve realized that the advice is to plan out a half a year ahead. We’ll get to that later, but should have already planned it. The main thing I’m thinking about is the first week in January. I’m dictated by school calendars, all the schools are closed. Hopefully things will be cheaper. Hopefully I’ll be able to get the time off work and I’m gonna figure out somewhere to go but planning-wise I’m—haven’t started.

Aislyn: I love the honesty. I think that’s, it’s good because a lot of people are probably in the same boat, myself included. Chloe, Mark, how about you?

Chloe: Well, I already know Mark’s going to be on, like, completely different wavelength than me, but I’m also kind of nowhere. I have a friend who’s going to Mexico. Yeah, kind of same time that you’re I guess thinking of traveling: the first week of January or like early January. And she’s, I think, gonna be in the Tulum area, but she was, like, wondering if I wanted to come to, like, Mexico City with her and explore, so I think there’s some ideas floating around. But I don’t think there have been any definitives that have been made yet.

Mark: I, I have my travel plan till about mid-February. But that’s because I have a very busy work schedule for Q4. So I’m going to Australia for a story. I’m going to Cannes for the big travel fair that a lot of us go to, I’m going to Puglia for another travel conference. So a lot of my travel is not the fun stuff.

It’ll be great fun, but it’s planned because I had to plan ahead. But I am gonna go, my birthday’s in the winter, and my favorite thing to do for my birthday is go to Venice in February, because I think Venice in February is the Venice of your dreams, not your nightmares. And I don’t know why anyone would go in the summer, and it baffles me that people don’t flood there in the winter.

Aislyn: Why? I feel like we need to know more.

Mark: Because Venice is like a Henry James novel brought to life. It is glamorous, decayed, a little naughty. You’re not quite sure what’s going on or what is around the corner. And in winter, you wander through these damp streets and it starts snowing and you duck into a café and have a little ombretto of prosecco and then you go back out into the streets, it gets dark really early and you sit in candlelit restaurants that are half full people and you just think, “Oh, this. This is beautiful.” In July, you walk in, you smell the canal, turn around and think, “Why did I come?”

Tim: I’m sold.

Aislyn: I know. Let’s all go.

Chloe: I know. Oh my gosh, I remember Mark when you were writing about, like, the off-season destinations piece, and then you were just, like, so strongly for Venice in February, and I was like, I need a full explanation. So it’s nice to hear, like, why in your words, and it’s just, like, so poetic. Oh my god.

Aislyn: I feel like there’s an important distinction that we need to make and it came up when we were planning for this episode. When does winter begin for you? We know that the first day of winter is technically, you know, around the solstice, right? December 21st. But what do you think personally?

Tim: Winter doesn’t really exist where I live in Southern California. It starts and ends when I drive up and back down a local mountain, like, it’s a Mammoth Lakes or Big Bear. And at about, I don’t know, 6,000 feet, you start to see snow. But it’s certainly not Thanksgiving or December when it’s still warm and sunny.

Although around here, people love to dress up in woolly hats and coats in this first sign of a slightly chilly wind. Like hotels in Santa Monica have big log fires and, you know, like everyone’s desperate to pretend it’s winter, but it is not.

Chloe: I feel like for me, like, it is like right after Thanksgiving because I feel like the prewinter holiday, it gets you in the mood, you know? To me that’s when the winter starts is when you just like start taking down all the fall stuff and, like, I just feel like all of December, that’s when winter starts, you know, weather-wise.

Aislyn: Winter is a state of mind.

Chloe: Yes, it is. It is. As is fall when the pumpkin spice lattes comes out. Although, like, I had a pumpkin spice latte the other day and it felt so wrong. I was sweating.

Mark: But I think they’re just, they’re just wrong. I was gonna say it’s just wrong as an idea, not as timing.

Tim: That’s wrong any time of year, yeah.

Aislyn: Even in the depths of winter, when you’re just freezing, you wouldn’t want to clutch a steaming hot pumpkin spice latte.

Mark: You couldn’t—I don’t know, I don’t know what it would take for me to ingest something that toxic. I’d rather drink nuclear waste.

Tim: You gotta ask for just one pump of the toxic syrup, but then that’s getting into the personalization thing. Maybe one, one a year. Just buy it and have a sip.

Aislyn: Yeah, there you go. What about, Mark, for you? When does winter begin?

Mark: I’m going to reveal my cards a little here. I am not a skier, a snowboarder, and growing up in Britain, I don’t go somewhere to find more cold. I grew up in Britain surrounded by rain. In America, I have lived in Chicago and New York where winter is with a capital W.

So for me, winter is all about, what can you do to try and offset what you’re enduring. So my trips are always—so I think winter starts when the weather really bites. January, February, when you get those minus temperatures, even in Fahrenheit, that’s winter to me, and that’s when I’m on a plane to the Caribbean.

Aislyn: I feel like this is a good—

Tim: I guess I’m the opposite.

Aislyn: What? You’re the opposite?

Tim: I’m the opposite, yeah. I was barbecuing outside yesterday in the sun in early September, daydreaming about gloomy Scandinavia or snowy Jackson Hole or wherever, but then, you know, I’m lucky that I have this weather, but yeah, it’s just something different, isn’t it?

Aislyn:  Yeah, it’s nice to just have a change in pace, a change from whatever it is you’re used to, whether that’s sun or gray or snow. Is anyone else a skier or a snowboarder, a snow lover in some way or form?

Chloe: Well, I tested it out. Like this past February, I went to Whistler. I’ve never gone skiing before. So this was trial by fire.

Aislyn: And?

Chloe: I decided I was not much of a skier when I ran into the magic carpet and a very kind Australian helped me up. But I spent the next day at, like, the village and I, I think I just underestimated, like, even though I didn’t like skiing or the outdoor activities, I still really enjoyed my time in the village.

I went to an escape room, you know, I had some drinks with friends, I was just, like, walking around shopping. I was like, “Oh, my God, there’s a Lululemon here.” I’m kind of glad my first experience was there where it was, like, I had the option to do things that weren’t ski activities if I didn’t like skiing,

Mark: You see, I think in North America we have quite a view of that, because the North American resorts tend to be high enough that they rarely suffer from a dearth of snow. So they— yes, there are other things to do, but they’re never worried that you won’t be able to ski or snowboard, it’s just a bonus, whereas I think if you’re like me, I love going to Gstaad, I love going to Cortina D’Ampezzo, because those are very low resorts, so they often struggle.

I was in Gstaad in January, and I was there for the first day of snow, which was January 9th. And the European ski resorts are sort of configured to be kind of, “If you want to ski, sure. But if not, just take the lift to the top of the mountain, and there’s a gourmet restaurant there for the views.”

Tim: Yeah, we had a whole, couple of pieces on après-ski on the site a couple of years ago. But I personally, I, I’ve done skiing and snowboarding and things—snowboarding, I’m terrible at. But last year in Yellowstone in the winter, [I] did snowshoeing and cross-country skiing, both for the first time.

And I put up a picture of the snowshoeing and someone commented like, “I don’t get the appeal. It’s just like harder, colder hiking.” But I loved it. The, the, the silence, the pure snow that you’re walking on, the fact that you might fall in a big hole, and just the wind and the swish of the snowshoes, it was really calm. And yeah, and cross-country skiing as well. And all the roads were closed. So the place was so much quieter and no, no cars around, closed roads. But I didn’t realize there’s no way to slow down or stop.

You can’t, you’ve got to keep your skis parallel cross-country skiing. So when it’s a downhill, you just hope for the best.

Aislyn: There’s no pizza.

Tim: It’s interesting. Yeah. Mark’s face. I enjoyed it.

Mark: This is the pumpkin spice latte of activities to me. I feel like I’m just like, “Why would you do this?”

Tim: But it’s of like, you do a morning of something like that—

Aislyn: Yeah, yeah,

Tim: —then an afternoon in a hot tub, supper, repeat.

Aislyn: Yeah, exactly. I’m with you. And I think there’s just something so magical about being outside in the trees with the snow, you know, like you’re saying the quiet and it’s just very transporting.

Alright, well. I think this is a good time to talk a little bit about actual destinations. And Mark, you write these stories for us each month about where travelers should go next. Recently, you wrote about where travelers should go in November, and I think that you’re thinking about December. Do you want to talk about some of your recommendations?

Mark: You’re seeing behind the scenes here, because Chloe and I literally just talked because we work on this together. I think, you know, again, I do think that if you’re going to go somewhere for the winter, go somewhere that does winter well. So Vienna is, is a destination that when you picture it, you don’t think of Vienna in the summer when you’re biking by the Danube.

You think glühwein and glittery lights. Vienna has wonderful, wonderful Christmas markets and it’s got a lot of new, great new hotels. I, of course, want to go somewhere warm and I think it’s really easy to forget that our winter is Down Under’s summer. And if you go, we talked about going to North Island in New Zealand for a food and wine festival.

And remember, somewhere like New Zealand is glorious in the summer. And it’s when we’re at our most miserable in the Northern Hemisphere, that’s amazing. And I would be down in Miami for Basel every December. I know it’s chaos and everyone pretends they hate it and then they go and they have a great time and they come back and they’re like, “Oh it was terrible, too many people, oh it was awful.”

No, it’s not. It’s kind of wonderful and chaotic.

Aislyn: I’ve never been. What do you like about it? Like, what’s the fun part about the chaos?

Mark: I think Miami is a chaotic city and so I like when a city leans into what it’s supposed to be. And when 19 things are going on at once, half of it’s in Spanish, half of it’s in English. There’s this thing there, everyone, there’s like permanent FOMO. And it, it just feels the most Miami-Miami you can get.

And I love that. I love that sense of it’s absolutely, relentlessly nonstop. And that’s kind of part of what makes—Miami’s one of my favorite places. And it’s, I used to go there for months at a time and I love that relentlessness.

Tim: That’s interesting. That reminds me about what I love about my favorite music festivals is you, at the end of it, you feel like you could have relived it five different ways.

Mark: That’s a great— thank you. That’s much more succinct. Yes. I would also say, I love southern Belize. Placencia in southern Belize has, has been gussied up since I first went, but it’s a gorgeous part of Belize and it doesn’t have the sand flies that Caye Caulker in the north does. But there’s a winter marathon in that part of Belize.

So if you want to go somewhere warm, but be active rather than just sit on the beach, I think southern Belize is best of both worlds. You can do that in December.

Tim: That’s interesting. Yeah, I went to Belize in March, but I was further north up in San Pedro and in the snorkeling and the diving around the reef there is amazing. And we went to the western side and you can just see it starting to get more developed and tracts are being brought up for hotels. It definitely feels like that whole stretch of coast is changing. And now it’s a good, I mean, it’s already fairly developed, but now is a good time to go.

Mark: I had a great, a travel agent say to me once, “Look, if you want to go to the Maldives, but you don’t want to hike halfway around the world, the fringing reefs in Belize are four and a half hours from the East Coast, and you’re getting that Maldivian experience because the water is bright blue, the reefs are right there, and it does get overlooked.”

I think it’s the country in Central America, partly because it’s English speaking, it has a very different heritage from the rest of Central America. I think people tend to be like, “Oh yeah, Belize.” It’s the last response in a trivia question asking you to list the countries in Central America.

Tim: It’s also small, it’s a small country, easy to get around, lots to do in a small space. And as, as you were mentioning in the where to go November piece, there’s a whole Garifuna festival happening that time of year.

Aislyn: What is that festival?

Mark: We often overlook the Caribbean Indigenous culture that there was because it got so erased by waves of settlement. And the Garifuna is essentially, there is still quite a significant presence in that part of Belize for the Indigenous people.

It’s a remixed version of their culture. It’s definitely been influenced by the arrival of others, but it is a glimpse sort of past the waves of settlement. And it’s a great chance to see a very different version of Central America.

Aislyn: Oh, I love that.

Tim: Yeah. My only experience is in a restaurant, a cultural center in San Pedro, and they had drumming and dancing and some amazing hudut, I think it’s called, like a fish stew with coconut milk and scotch bonnet peppers and yams. It’s delicious.

Aislyn: Yum. Well, you mentioned Christmas markets, Mark, and when we were planning for this episode, both Tim and Chloe got very excited about the idea of Christmas markets. Why, why are those so appealing to you in Europe, particularly, like doing a Christmas market tour?

Chloe: Yeah, I guess, like, for me it’s because I haven’t been to, like, any Christmas markets, but I think it was Claudia who’s part of, like, the video team at AFAR and she had a video on the Christmas markets of Salzburg and the traditions. Like I think they had a Krampus run where people dressed up like Krampus, you know, ran amok. Um, so I don’t know, it was just, like, those cool traditions and I think just the atmosphere of everything just made me, like, “Oh man, like, that’s something I would really want to do.”

Tim: It’s more just, like, just the idea of them and the photos you see, and the food and the, uh, glühwein and then, you know, the little huts with all the twinkling lights on it. It just feels like Christmas.

You know, I’ve been to Bruges in December and that was kind of like that, but yeah, nothing the like the, uh, the real ones. Alma Waterways does a cruise on the Rhine that goes through Cologne, Strasbourg, and some other places. I just thought that would be quite a nice thing to do.

Mark: I would also give—Can I, can I make a pitch for an unexpected Christmas market that I went to as a kid and really love and we featured last December? Naples is where the nativity scene as we know it originated. And because of Capodimonte and the porcelain that’s made around there, they still have an incredible Christmas ornament manufacturing industry.

And the presepe, the nativities, are all around Naples. And Naples has wonderful Christmas markets. And I think it’s unexpected because we think of it as so middle European.

Tim: I’ll give you a sneak preview on a piece that we’ve got coming up on a writer from England as well, is writing a piece for us about why Stockholm is delightfully Christmasy as well. So keep an eye out for that. There’s also, we had an article a year or so ago about Christmas markets in the U.S. There’s plenty here. There’s one really near me, Julefest in Solvang, the Danish version—

Aislyn: Oh, cool.

Tim: in California. I’ve never been to, I think I might go this year. Savannah, Georgia, has one. There’s a Christkindlmarket in Chicago. So, you know, they’re everywhere.

Aislyn: You know, I have to say, I was in Savannah last December and I loved it. It was such a fun place to be in December because they really blow out the holidays there. Like, if you’ve seen that movie, Midnight in the Garden of Good and Evil, you might have a sense of what I mean, but everywhere you turn there are wreaths and ribbons and lights and it just felt so celebratory and magical that I was, I was really impressed.

Mark: You know where else is an unexpected Christmas hub? Is San Diego. San Diego has several of America’s largest Christmas stores. Mostly because the houses are big and people are rich and they have room for things. But if you love Christmas, just Google San Diego Christmas stores and it will blow your mind.

Aislyn: Like shopping for lights and ornaments, things like that?

Mark: A little bit more than that. I mean, we’re talking, like, 30,000-square-foot spaces with 10,000-square-foot warehouses where you can buy, you know, automated Santas and personally engraved ornaments. I mean, imagine a mall, but just Christmas.

Aislyn: So then I wonder, the Christmas lights must be really fun to drive around in San Diego. They must, like, go all out.

Mark: It’s more that they’re selling, selling you Christmas rather than celebrating Christmas, do you know—I think it’s more. City Lights is the big one, which is run by a British guy, but there’s also Roger’s Gardens, uh, in Corona del Mar, a couple of those. They’re really extraordinary.

Aislyn: So go with a couple empty suitcases and get your mechanical Santa. That makes me think, are there any kind of dream winter destinations that you all have?

Chloe: Yeah, I guess I have like two. OK, so I have one that’s, like, a warm-weather one. And then I have, like, a cold-weather one. So warm-weather one, speaking to, like, my family’s heritage, like, I would love to go to the Philippines in the wintertime, because—and not a lot of people know this—but it has, like, the longest Christmas season of any country.

Christmas season starts like, it starts ramping up, like, in August. So, like, it’s already the beginning of Christmas, um, and it lasts until, like, you know, I guess a little bit after the New Year. So, the festivities are crazy, um, you know, people just love celebrating Christmas, and there are a lot of, like, different traditions and, like, the lights and everything like that.

And then, cold-weather destination. Excuse the car horn. Cold-weather destination, I would love to go to Montreal. I think, because I know that, you know, they do like winter big there. I know there’s like Igloofest, which is like a whole electronic music festival that happens.

And I think they just really embrace the winter. They have, like, was it Luminothérapie where it’s like they have a whole, I guess, set of temporary public art installations that are set up throughout the season. And [they] just kind of get people kind of embracing winter and, you know, in the festivity mood, despite being in, like, such a freaking cold place. So those are my two dream destinations.

Aislyn: I love it.

Mark: I want to go to Japan, because Japan as a culture, obviously, is not a Christian culture. Firstly, I want to experience Kentucky Fried Chicken on Christmas Day, which is the contemporary Japanese tradition. And I’d love to experience that. But I’d also, I want to see fukubukuro, which are, every new year, Japan’s stores sell Lucky Dip bags, which are good luck for the new year. And so it’s sort of, you go into each store and there will be for, you know, the equivalent of 20 bucks, it’ll be guaranteed 50 bucks worth of stuff. And I just love the idea of all these fukubukuro and it’s a really, you know, it’s a Japanese tradition that has sort of been yoked onto our Christmas season and I want to sort of see that for myself.

Tim: I’d have to give a plus one to Montreal, but I’m not so sure about fast food on Christmas Day, having had Carl’s Jr. one Christmas in Palm Springs. I’d like to see more of America’s ski towns, like Telluride, Jackson Hole, places like that at that time year. I feel like I could explore more of those. And quite honestly, I’d love to just get back to London. I miss London in general, but especially that time of year. Concerts at the Royal Albert Hall and the Southbank Centre on the Thames, and just wandering between the pubs. Trying to get on the tubes with loads of shopping bags and getting a couple of pints to steel your nerves for that. I don’t know—

Mark: It’s quite a lyrical thing. This is like a day, sort of fever dream that we’re part of.

Tim: It is. I’m gonna make it reality.

Aislyn: OK, dreaming is important, but what about the realities of traveling? We’ll get into tips for navigating winter travel after a special word from our sponsor. But first, a quick piece of winter travel trivia. Here’s the question: What is the snowiest city in the world? A) Syracuse, New York. B) Chamonix, France. C) Aomori City, Japan. Or D) Quebec City, Canada. I’ll reveal the answer after the break.

And we’re back. Still wondering about the snowiest city in the world? The answer is C, Aomori City in northern Japan. It gets about 26 feet of snow each year, thanks to chilly Siberian winds that sweep in from the Northwest. Brr. And now back to the show.

Aislyn: We’ve been talking a lot about fantasies and dreams but we have to, you know, face the reality of traveling. You have to travel to get somewhere, right? So let’s talk a little bit about intel and some tips maybe for navigating this winter season.

I mean, this summer was pretty intense, right? Do you anticipate, I mean, if anyone has a crystal ball, do you anticipate this winter being equally intense from a travel perspective?

Mark: Remember the issue is, it doesn’t matter how much we’re traveling, there is still a dearth of air traffic controllers and pilots who weren’t hired over the pandemic. So the travel industry, whatever we do, it’s already at breaking point, operationally. And we saw that—I was caught up at the end of August, the whole of U.K. airspace shut down for a day because someone filed the wrong flight plan.

And it canceled every flight into the U.K. I was transiting from Greece to the U.K. to the U.S., and I ended up booking a miles flight from Athens to JFK as a replacement. And I think that’s always one of my tips. I use my miles for emergencies. I don’t use them. They sit in my account so that when I need a flight that’s going to be really expensive, I don’t care.

And I always think in times like these when there are—if you catch a sort of stress point or a crisis, check and see if you’ve got any miles that you can throw at the problem because it doesn’t feel like money down the drain.

Tim: I was just looking at the TSA screening numbers for Labor Day weekend. And they screened 9. 5 million people, up 11 percent increase on 2019. So, I imagine it’s going to be the same for Thanksgiving, Christmas itself, New Year, you know those times. For me, I always, in the winter, I try and think about airports with more reliable weather. So luckily L.A., London on the whole, if something’s going wrong, it’s more technical, but you never know these days, but yeah, I would definitely think carefully about which airport and their local weather patterns.

Mark: Atlanta, not Chicago in other words. If you’re going indirect, take a Delta flight via Atlanta, not United via Chicago because over under Chicago is likelier to have tougher weather.

Tim: Another, another point towards winter sun as well.

Aislyn: Tim, you mentioned this earlier in terms of the ideal time to book flights. What do you think when it comes to winter travel? Of course it depends on, you know, when in winter, you know, if you’re going to do holiday travel versus going someplace in January, February, but any tips there?

Tim: There was an email from Going.com: “Book those winter holiday flights now.” And they, they say, book opposite seasons. So if you’re going in Christmas, summer is the time to book. And the point they made was, if you’re buying a winter coat, you’d get it in the summer and vice versa. So it’s not a bad thing to bear in mind, but too late for this year.

Mark: But I also think, it is, just let’s establish once and for all, it is an utter canard, it is a canard, that there is any magic window, any magic date, any magic time. It is repeatedly burped out by travel companies in order to get us all talking about them, that they have identified the 13th day of December as the one, you know, the 43rd of January as the day to—there are lots of ways to get great deals. A lot of them involve signing up for services like Airfarewatchdog or Going that tell you when a sale on certain routes that you’re interested in happens. Those sales can happen at any point or at any time. And if you are listening to this and thinking, “Oh gosh, I’ve missed that window,” don’t let marketing needs make—guilt you into thinking, “I have no hope.”

Tim: And also, some of these times, they don’t, you’re not going to see sales, right? So, uh, I did see that [Google] Flights has launched a new sort of tool when you, if you’re tracking flights, it will give you the price history for that time. I’m finding that quite useful. I’m trying to get five flights back to the U.K. next summer, and they’re not going to really change at all because it’s summer holiday time. I think the same probably applies for winter, but there are more tools out there you can use.

Mark: And don’t forget—and I think this is one of those revelations when you think about it—Thanksgiving is only a holiday for America. For the rest of the world, it’s just a random Thursday in November. If you want to score a cheap empty flight to Europe, the only other people on that flight from America are Americans going to visit their European family to make the most of the holiday. It’s one of the cheapest, best times to fly anywhere other than domestically.

Chloe: Yeah. I remember when I was living in Spain, I think it was, like, yeah, during Thanksgiving, it was like, “Where should I go?” And I was like, “You know what? Instead of eating Thanksgiving turkey, I’m going to go to Turkey.” And it was great.

Aislyn: I love that! Such a good idea.

Tim: Is that true for Christmas day as well itself? Like, is that a cheap day to fly, Christmas day? So basically just ignore the holidays, like don’t celebrate. It’s like, um, Disneyland on the Superbowl is supposed to be the best day, right?

Aislyn: Yeah, yeah. Or to go to Costco.

Tim: Or both if you really fancy.

Aislyn: So Mark and Tim, you mentioned a while back that you have a favorite time to travel around the winter holidays. Do you want to share that tip?

Tim: Yeah, I mean, my favorite time is between Thanksgiving and Christmas. I mean, I went to Aspen and the slopes were fairly empty. I went to Fiji and the resort only had two or three other couples in it. I think, it’s a tough time to take off with the build up to the holidays and work and end of year rush and whatever you’ve got going on in your daily life. But if you can take that time out, it seems like they’re definitely less people on the road.

Mark: I would also say Las Vegas is one of my absolute favorite places in the world and if you want, if you like me love Las Vegas, uh, by far the cheapest time to go is exactly that window. Because it’s the time when no one is really thinking about Vegas. New Year’s Eve, you’ll pay you know, $8,000 dollars for a hotel room. That same hotel room three weeks earlier will probably be $300 and the weather’s fine, Vegas chugs along. Same old, same old, great time to go.

Tim: How many times have you been to Vegas?

Mark: Uh, oh, I mean I’ve lost count. It is the place, if you said to me, “Where in America do you want to go on a plane tomorrow?” I’d go to Las Vegas.

Aislyn: How many times a year do you go?

Mark: At least a couple and for fun. I mean, we travel a lot for work, but I go on my own dime. I’ve lived in America for the majority of my life, but someone said to me, “Las Vegas is what smart Europeans hope America is like, and it’s what smart Americans worry America is like.” And I will always be European in that way. I just love it. It’s sort of like, if Cher were a place, she would be Las Vegas. And you’re like, “Good for you, keep trucking.” And I feel like Las Vegas is like “Bring it on. You know what you want? I’m going to give it to you in spades.”

Tim: Yeah, it’s one of those places you’re always really excited to go there and always really excited to leave at the end.

Chloe: Now I kind of want to do Thanksgiving in Vegas.

Aislyn: There you go.

Chloe: It sounds like it would be amazing.

Aislyn: Tim, you had mentioned that when we were talking about kind of thinking about weather conditions that you’d had to postpone a Yosemite trip a couple years back that you had planned for the winter. Do you want to tell that story?

Tim: We had a few days booked in a cabin, actually, within the park. And, you know, that time of year, that kind of place, you’re keeping an eye on the weather and it didn’t look good. And I had visions of being on the side of the road with three young children waiting for help. And I, you know, you’ve got, you can get chains for the tires and you can check Waze and the weather reports, but the car’s not even four-wheel drive.

So it was a bit daunting and then they, they just canceled it. The hotel was closed. But so, yeah, I mean, we ended up going two months later and had a great time. So, you know, you just need to hold those points in reserve and keep your eye on things and have a backup plan.

Aislyn: Yeah.

Tim: I really enjoyed seeing the national parks in the winter, like Yosemite and Yellowstone, a very different experience.

Aislyn: Yeah.

Tim: But if you’re not with a tour group or, you know, organized trip, it is a bit more, you know, dicey, it can be.

Mark: Can I suggest next time you invest in a policy with Sensible Weather, the new insurance company? Which I think if people haven’t come across it, it’s essentially the insurance against bad weather, give or take, it doesn’t cover everything, but you can opt into this when you book from certain platforms and it will automatically give you some money back if the weather you were expecting is not dutifully delivered by the planet.

Aislyn: It’s such an interesting, we just did an episode about travel insurance and I interviewed Nick Kavanaugh, the guy who, who cofounded it. And I was like, “So really, if you have a bad day, it rains, you can’t do what you want to do, that’s, that’s it? That’s the whole idea?” It’s brilliant. Or skiing, you know, if you’re skiing, the weather isn’t what you were hoping to be.

That’s so great. Great policy. Tim, what do you, what did you like about Yellowstone? And Yosemite in the winter, like, what was the appeal for you?

Tim: Well, I mean, I forget the numbers, but Yellowstone is a million, million visitors in July and 70,000 something in February, you know. You don’t get those lines of cars taking photos of bison. You just, just have it to yourself.

There’s, there were a few photographers there and a few, a few intrepid winter hiker types, but, you know, just lack of other people as well, really I mean, and the picturesque nature of it.

Chloe: Is there, like, animals running around? Or are they all hibernating?

Tim: Yeah, no, loads, like, loads of them. Yeah.

Aislyn: And the wolves in Yellowstone are supposed to be—like, you can actually go on a guided tour to, if you want to specifically see the wolves there, which I think would be super cool. And literally cold.

Tim: I didn’t see them, and we were actually supposed to go on a husky-pulled sled, which got canceled because it was too slushy, so I should have had Sensible Weather for that as well.

Aislyn: Yeah, see?

Mark: I also think, don’t forget the South Rim of the Grand Canyon is open year round and you will have a very different experience in the Grand Canyon, but it will be significantly less congested. As long as, I mean, January, February, we’re talking, we’re not saying go, go between Christmas and New Year, but the Bright Angel Trail will be much less Times Squareish in the countryside. So I think there’s something to be said for that.

Aislyn: Yeah. Are there any other national parks that you think would be interesting to explore in the winter, or that you have?

Tim: We got, um, married in Palm Springs and had a load of Brits over and took them for some pre–wedding day trips. And one of them was to Joshua Tree and it was the one day of the year it was snowing and seeing Joshua Tree covered in snow was quite interesting.

Aislyn: Yeah, wow.

Tim: Especially at night.

Chloe: Yeah, that’s true. Yeah, going to like Death Valley in the wintertime.

Aislyn: Right?

Chloe: That’s the move!

Aislyn: Yeah, it sure is. I know we’re not a bunch of skiers here, but do you have any tips on traveling with winter gear? Especially flying.

Tim: Rent it when you get there.

Aislyn: Yeah, don’t.

Mark: I do think, I think that even, I think unless you are a semi-pro-level sportsperson, I don’t know why people would travel with equipment like that. It’s expensive, it’s inconvenient, it will get damaged. Most places you go for these activities will rent good enough equipment for most amateurs to enjoy.

I think when people—you sort of see people sort of clinging to their surfboard or their skis in the airport. And I think, “Gosh, that’s made your experience more expensive, miserable. Why the heck didn’t you just rent it when you got there?”

Chloe: Yeah. It looks horrible. Well, for me, I guess I realized the value of, like, winter apparel, like the appeal of just like the functionality of it, um, like this past winter when I was, like, traveling from, like, you know, like Canada, Seattle, and then I went to Japan for a little bit.

It was like, I had a blue jacket and it was for skiing, but it had like zips, like zippers at the top. So you could remove the sleeves. And it was kind of great because, you know—

Aislyn: Oh, nice.

Chloe: —when you travel to, like, multiple countries, and then it’s like the winter is just so different there. I was like, “All right, let me just take this off. I have a vest now.” So I think, like, you know, the functionality of a lot of these, like, outdoor sports, like, apparel and clothing, it’s very useful if you’re traveling to different places, especially in the wintertime, when you know some place it’s going to be freezing. And then some places you can just, like, adjust and then still make it work and, you know, take up less space in your luggage, so you can buy the mechanical Santa.

Mark: Look, not, I’m not investing in an REI puffer or anything performance because not my world. But for people like me, I would say, Uniqlo produces really cheap, cheap, durable puffer jackets that squish down into the size of a pair of socks. And I think if you’re going to winter destinations, I will often pack a couple of those. And they are, if you double layer those, they’re a remarkable backstop that takes very little space because winter clothes are so bulky and those are essentially thermal vests that take up no space.

Tim: Where do you guys stand on wearing your bulky stuff on a plane versus packing it? Are you the person in the airport with the massive jacket and the hiking boots? Or would rather have two suitcases?

Mark: I just interviewed people, uh, about the fishing vest hack, and there, there are indeed special companies that produce clothing expressly for you to put your clothes in your clothes. But I think people who wear their bulkier stuff onto the plane are below people who put their bare feet on the seat in front, in passenger hierarchy.

Tim: I’d rather snuggle up to someone’s jacket than their bare arm though, if we’re sharing, um, an arm rest.

Aislyn: That’s true.

Mark: I don’t want to snuggle up to them, period! That’s the whole point! I paid for my own, please don’t have your giant puffer jacket providing me with an unwanted pillow. That is, I don’t—oh, no, no, no.

Chloe: OK, I’m the type of person who wears the bulky stuff on the plane.

Aislyn: You guys are so opposite.

Chloe: It’s like, no, Mark and I are the same in terms of, like, destinations and but like, how we travel is so different. But I am type of person, but it’s like, so useful, because as you said, like, turn my jacket into a pillow. And it’s like, you know, I usually take the window seat and usually there’s just—

Mark: You’re that person, aren’t you? You’re, you’re like that, like, that person who looks like a sort of walking igloo of clothes. And there’s little feet sticking out the bottom, and people can’t really tell when they try and identify you. You’ve got your hood down, and they’re not sure if you’re, who you are, that—you’re that person. There’s always one in the winter, on every plane.

Chloe: I’m like that person, like, all the time. Like, cause I’m just like, “You know what? No, no need for a carry-on. I could do a—I could just do a personal item.”

Aislyn: You’re not even doing carry-on: Wow, Chloe, that’s impressive. We’re going to need photo proof of this.

Mark: Anyone who does, anyone who wants to ignore me and buy one of the, it’s by a company ScotteVest and they are, if you wear them, you can’t tell that you’ve got three pairs of shoes and a handbag in each of the pockets, they’re quite remarkably designed.

Aislyn: I don’t know about that. I will wear, like, my puffer jacket on the plane, but then I take it off and I’ll either put it in my lap or if there’s space to put it up above a seat, I feel like I don’t need it—because it is huge. It takes up a lot of space in your suitcase, you know, and if you are going someplace cold, you want it. But yeah, the Uniqlo vests, those are, those are great.

Mark: No, I think, I, I packing in the winter, and this is, this is one of my big things. I don’t understand why there is a moral virtue in packing as little as you can. There is this weird sense that if you manage to board a plane without a carry-on, you have somehow hacked the system.

And I don’t necessarily carry my entire life with me, but just check a bag. I know it costs something, just check a bag. Put an AirTag in it, so you know where it is. It is not morally superior to somehow not have luggage. I, you, it’s just a choice. It’s like coffee with or without milk. Totally up to you. Tim.

Tim: It’s true. We can agree to disagree. I, I’ve started just getting down to one backpack for conferences. My son got his finger trapped in a bag—well, not trapped, but nicked by a baggage carousel in Cabo last month. I’m like, “If I can get off that plane and just walk out of the airport, no baggage carousel, no oversized luggage. And then get in the line for customs and just wait there instead, but you know, just not having to think about things and forget them, all of that. I’d much rather have one less pair of pants or whatever than to deal with that.”

Mark: I know, that’s fine. My point, Tim, the thing is, I don’t know where the moral superior— There is something that is, when someone says, “I never check any carry-on.” It’s a bit like saying, I don’t, you know, “I do 12 hours of community service every week.” You’re like, “You just, OK. Sure.” But there is a slight like—

Aislyn: Yeah, yes.

Mark: —the smugness is palpable. “Oh, you checked a bag.” Yes, I did because I can!

Chloe: OK, I wouldn’t say it’s, like, smugness, I would say it’s just more like, you know, like you love getting a good deal, like you love being able to—

Mark: No, it’s smugness. Don’t pretend. You’ve done it and been like, “Yes, I’m wearing all my clothes.”

Tim: It’s probably a whole other topic, but travel, travel is so hard. It’s hard. So when you get some hacks and you do it right, and you can, you can pat yourself on the back for, like, getting one journey right. And not having any mishaps,

Aislyn: Oh my God.

Tim: We should move on, Mark’s—

Mark: Ohhhh.

Aislyn: What about New Year’s travel, traveling for New Year’s specifically? Yay, nay?

Tim: I’ve always found there’s too much pressure on New Year’s Eve to be the best night of the year and it often wasn’t when I was younger. I’m just asleep by nine o’clock, 10 o’clock anyway, so, those days will come back, but yeah, I don’t travel for New Year at all. I don’t even make it up to see it. Well, actually no, I celebrate the East Coast New Year and then good.

Mark: That’s amazing.

Aislyn: Woo!

Mark: You’re like “I watch New Year on the East Coast, I can go to bed now.”

Tim: Well, if you’re watching it on TV, it’s just you’re just watching Times Square when everyone’s left and they’re just, they’re trying to drag it out for the West Coasters.

Mark: See, I think there’s a rule around New Year’s Eve. If you try and go to event destinations on New Year’s Eve, the Vegases, the Miamis, someone, a friend of mine who was a promoter in Miami, said that she made 40 percent of her money for the year on New Year’s Eve. You will pay through the nose. I think if you travel on New Year’s Eve, it is road trips only.

It is rent a cabin in the hills, you know, do a staycation. If you’d like to make New Year’s Eve a little special, make sure it’s not more than a couple of hours worth of trekking. And then, you won’t pay through the nose, you’re not going to a big event, but you’re just saying, “Hey, I want to treat myself.”

I think that’s a way to travel on New Year’s Eve and not think, “Gosh, I regret that expense.”

Aislyn: Yeah.

Tim: Yeah, the cabin with a few good friends, that’s a good idea.

Aislyn: Yeah. Yeah. Bottle of champagne. Chloe?

Chloe: Yeah, I guess I’m, like, I’m kind of conflicted because this is my first time that I will have the opportunity to experience a New York New Year’s. So, yeah, I don’t know where I stand cause usually our family, we have like a tradition of having, like, a karaoke party just at our, our house, which is, like, you know—

Aislyn: That’s fun.

Chloe: —cabinesque kind of atmosphere where it’s just, like, you know, just with family and stuff. But, you know, just being in New York for it. I mean, I don’t think I would do Times Square, but maybe, like, the couple hours trek would be like, you know, taking the El to, uh, get to my friend’s apartment kind of situation.

Cause I think with like crazy crowds, I don’t know, I feel like that might be, that might be a little too much and take all the joy out of it.

Mark: If there’s anyone listening who has gone to Times Square for New Year’s Eve and not regretted it, I’d love to hear because—

Aislyn: Ooh, that’s a poll we’ll do.

Mark: —no one I have ever met says anything other than, “Gosh. I’m glad I did that once.”

Aislyn: Yeah, yeah, “I can say I’ve done it. Check.”

Chloe: Yeah.

Aislyn: You know, I will say I, we didn’t do this intentionally, but about five or six years ago, I had the opportunity to go to Antarctica and it was right after Christmas and we were there for New Year’s. And that was my favorite New Year’s to date because we’re out, it’s still light, you know, it’s midnight and this pod of whales came up at the time and we were passing these gorgeous icebergs and everyone—it was like a French cruise, so it was a bunch of drunk French people, a bunch of drunk Russians, and then a handful of Americans and it was the best.

Mark: Oh, you win new year. I love you kept that quiet. That’s like all of us are just swooning That’s, that’s—you proved you should travel for new year because if you’re doing that, who wouldn’t want to do that,

Chloe: Screw family karaoke! Shoot!

Aislyn: Yeah. Penguins, drunk Russians, whales.

Chloe: Wow.

Aislyn: I, I think that’s it, y’all. That was, thank you so much. This was delightful as usual,

Tim: Great.

Chloe: Great to see everybody and talking with everybody.

Aislyn: Yeah, we’ll see you next season.

Tim: See you next season.

Chloe: Same time, next season.

Aislyn: Yeah, same time next season. There you go. Alright,

Aislyn: Thanks for listening this season. AFAR’s Where to Go 2024 list comes out in November, and we’ll be exploring that in the first episode of next season. We’ll also link to Mark’s Where to Go in November and December stories in the show notes, as well as to Mark, Chloe, and Tim’s social media handles, in case you want to follow them—or just, you know, disagree with them about their controversial opinions on pumpkin spice lattes and packing winter gear.

We’ll see you next year! As a final farewell, a few outtakes from this episode:

Aislyn: Chloe, would you mind turning your gain down just a touch? I want to, and can we test that out?

Chloe: Yeah.

Aislyn: Will you just tell me about what you had for breakfast this morning?

Chloe: I made myself—

Aislyn: OK. You can go back up a little bit.

Chloe: —yeah, some eggs—

Aislyn: A little bit more.

Chloe: —toast, and then I had an Oreo with yogurt.

Aislyn: Like dipping it in the yogurt?

Chloe: Well, I just like, made a makeshift parfait. I got, like, Greek yogurt and then I put an Oreo in it.

Mark: Is that a parfait? Or is it just an excuse to have cookies for breakfast? American breakfasts are just an excuse to have cake. Just an excuse to have cake.

Aislyn: And we love it.

Chloe: And we stand by it.

Tim: I’ll never forget the first time seeing a man in a suit, eating an IHOP breakfast in Austin, Texas, and just a bundle of, like, whipped cream and I said, “What is going on here?”


Chloe: I feel like Mark is disgusted by me. I don’t even—

Mark: Quietly disgusted.

Chloe: Like, I’ve worn pants as a scarf before. So.

Mark: No, but—

Tim: I think you should travel next him in all the puffer jackets, but then no shoes or

socks and just—

Aislyn: Yeah. And put your feet on the back of his arm rest.

Mark: As I short circuit.

Ready for more unpacking? Visit afar.com, and be sure to follow us on Instagram and Twitter. The magazine is @afarmedia. If you enjoyed today’s exploration, I hope you’ll come back for more great stories. Subscribing makes this easy! You can find Unpacked on Apple Podcasts, Spotify, or your favorite podcast platform. And be sure to rate and review the show. It helps other travelers find it. We also want to hear from you: Is there a travel dilemma, trend, or topic you’d like us to explore? Drop us a line at afar.com/feedback or email us at unpacked@afar.com.

This has been Unpacked, a production of AFAR Media. The podcast is produced by Aislyn Greene and Nikki Galteland. Music composition by Chris Colin.

And remember: The world is complicated. We’re here to help you unpack it.