What kind of traveler are you: a super planner who finalizes itineraries months in advance, or the spontaneous sort who’ll book a flight to Puerto Rico for this weekend? Did you used to be able to drop everything—and then you had kids? We hear ya. But you don’t have to abandon your past life to embrace a last-minute flight deal or explore a city with no set agenda. Just ask Busy Philipps.
As a mother of two who’s always balancing multiple projects, Los Angeles–based actress Philipps likes leaving her hectic life behind for a few days to take her family on a quick weekend getaway.
She wants to help the super planners put down the itinerary and embrace the fun and freedom of booking a spontaneous vacation. That’s why she’s partnering with HotelTonight to find America’s biggest planners and surprise them with a last-minute getaway. The winners won’t know where they’re going until a few days before they leave (not so different from AFAR’s Spin the Globe series).
When we sat down with Philipps to learn more about the contest, she shared her best travel tips: the one thing she won’t fly without, ways to keep kids happy on a long trip, and how she recovered from a big packing mishap. (Hint: Always bring a bathing suit.)
Interview has been edited for length/clarity.
Why spontaneous travel? Have you ever been a planner?
I’ve always been a spontaneous traveler. Obviously you want schedules to line up if you’re traveling with friends, but there’s something really nice to not having such a set idea of what your trip is going to be. I think it really helps you connect better with a destination.
What was one of your favorite last-minute trips?
Years ago, my boyfriend at the time and I both had a weekend off of work, and we wanted to go somewhere, so we looked at plane tickets first. There was a crazy deal from L.A. to Seattle, and I had never been to Seattle, so we said, “Let’s just do that!” We didn’t really plan anything, and this was before smartphones, so we just had to walk around the city and explore. It was really fun—we ended up going to the art museum, we went to see them throw the fish at [Pike Place] market, and we stumbled upon a great antique bookstore. It ended up being a very bonding thing, and if you’re open to the spontaneity of it, you won’t be so tied to expectations. Really fun, weird, cool things will happen.
What tips do you have for traveling with kids?
My children are the best travelers. My friend Christa Miller from Cougar Town told me years ago that before a long-haul flight, [you shouldn’t] let your kids watch TV for 24 hours. And then they get on board, and they’re glued to the TV! When you’re entering a long-haul flight with kids, you have to go into it knowing it’s going to be terrible. So that way, anything other than terrible is a delight. Even on this trip, my 11-year-old spilled an entire can of Coke on her seat during the first hour. But because I’ve been a mother for 11 years, we had a complete change of clothes, even for the 11-year-old, because we know that all bets are off on an airplane.
Is there any travel gear you always fly with?
I wear compression socks and leggings on long-haul flights. I have a friend who just had a blood clot from travel recently, and I don’t think it’s worth messing with. I’m not embarrassed by it at all. Whatever, I’m young and hot, and [wearing them] truly means nothing other than you don’t want to die of a blood clot!
Why do you think spontaneous travel around the holidays is a good idea?
There are those obligatory trips to see family that for a lot of people can be really stressful, and to be able to balance it with something that’s purely for you is fun. It helps you just get out of there and have a great two nights somewhere during those weeks off. The great thing about HotelTonight.com over the holidays is that there aren’t any minimum stays required. [And] it’s a very curated list. They make it very easy to narrow down the options, like “basic” (that’s not for me); “hip,” which is more designer, cool; and then “luxe,” which is where I mostly tend to go toward.
How do you roll with the punches when you’re making quick decisions?
Part of the joy of spontaneous travel is that things aren’t going to work out perfectly, but you’re just in a different headspace. It’s like when my family and I did a spontaneous trip to Palm Springs, and when we unpacked, I realized I didn’t pack any underwear. None, not any underwear other than the ones that were on my person. Everywhere was closed because it was around midnight, so I just waited until the next day and wore my bathing suit until I went to the store—don’t judge me.
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