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12 Months of Travel in 20 Instagrams

A year in the life of one of AFAR's co-founders

According to United Airlines, I’ve earned 112,800 (premier qualifying) miles in 2015. And adding up the miles on the various other carriers I’m somewhere in the ballpark of 125,000. All the points-junkies out there are probably thinking, “small potatoes,” but really, this year wasn’t so much about how many places I traveled to or the distance it took to get there, but rather the time I spent in those places to have deeper and richer experiences.

In the end, 2015 was all about the people I had the good fortune of connecting with combined with some spectacular settings. We've already shared our list of where to go in 2016, but you can never have too much travel inspiration, so here is a snapshot of a year in travel that  will maybe give you a few ideas.

1. New Years: Aspen, Colorado

My year started in Aspen, one of my favorite places in the world. Brunch at Cloud Nine with a 1.5L bottle of a delicious Italian Barbaresco, a charcuterie-and-cheese plate, and close friends was a great way to start the year. If you’re thinking about getting a group of friends together for a memorable time, Aspen and Cloud Nine brunch should be at the top of your list.

2. January: Cuba!
The day after Obama announced he was easing travel restrictions to Cuba, my co-founder, Greg Sullivan, and I landed in Havana. It was a fascinating experience to be in a country that had been closed to most Americans for so long on the eve of a transition. Not only did we find ourselves crammed into a small hotel conference room with a gaggle of reporters, U.S. Congressmen, and U.S. Senators, but we also ended up immersed in local culture at the home of a waiter we had met. His wife was a yoga instructor—and what better way to exercise and meet interesting locals than take a yoga class taught by a new friend?

3. February: Montreal, Canada
Go Habs! Canadians love their hockey and there is no place that love runs deeper than in Montreal. From our corner seats at the Bell Centre, we watched the Canadiens play the NY Rangers (and lose in an overtime shootout). Bucket list…check! Even if sports aren't your thing, there is something special about watching an iconic sport in an iconic stadium.

4. March: Charleston, South Carolina

I’ve met many good friends in Charleston because of

AFAR Experiences. Highlights of my time there included sitting with artist Jonathan Green in his living room studying his work, and an oyster roast courtesy of renowned chef, The Ordinary's Mike Lata (rocking out above), out at Bowens Island.

5. Later in March: Cancun, Mexico

I headed to Mexico to reconnect with myself over a much-needed long weekend. Only a 3.5 hour flight from NYC, Rosewood Mayakoba gives you the space, time, and ambience to really relax. My favorite part of the weekend was dinner underneath the Ceiba tree.

6. April: New Orleans, Louisiana

En route to NOLA
Easter was a great time of year to visit NOLA. The weather was beautiful and the city was festive. We found a great spot to rent on VRBO in the Garden District above a design shop; it was the perfect location.

7. May: Montreal, Canada (again)

Bonne nuit, Montreal
I visited Montreal a lot in 2015 and in May it was for a conference. C2MTL is a creativity and commerce conference that attracts interesting and interested global citizens from all over the world, so if you want to expand your database, this is a good place to do it.

8. June: Switzerland
Our “Grand Tour” of Switzerland featured eight different places in eight nights, and while it was quite a whirlwind, it allowed me to understand the diversity of Switzerland and all of the new things going on in the country. I was blown away by Ticino, the Italian speaking part of the country, and by the Switzerland's incredible hotels. It’s a definite must!

9. July: Iceland
I fell in love with Iceland thanks to Lindblad Expeditions. Their Iceland expedition was a new offering that combined two days on land with 3 days at sea. Lindblad puts a lot of emphasis on meeting locals and immersing in the culture—very in sync with our own philosophy. Jacob Edgar, founder of music label Cumbancha, curates musical talent for the expeditions, including acts such as the local folk band Ylja. Taking in the breathtaking views of Iceland while rocking out with local musical talent is a cherished memory.

10. Later in July: Cruising the Mediterranean
I spent eight days aboard the Paul Gaugin ship, Tere Moana, cruising from Athens to Venice for a friend’s birthday party. While Croatia’s coastline blew me away, and I’ve never swam in more perfect waters than those of the Dalmatian Coast, I fell in love with the Greek Isles once again and will be back next summer.

11. August: Back to Aspen, Colorado
I come for the Aspen winters but stay for the summers. In fact, summer in Aspen is so beautiful that I actually visited twice in August. There are so many activities to enjoy; coming here is a practice in wellness. I stayed at the Gant on this trip. It's perfect for families, groups of friends, or even a company retreat.

12. August (part II): Newport, Rhode Island
We headed to Newport for a company retreat and stayed at the Castle Hill Inn. It’s a 15-minute drive from Newport and such an ideal spot for a New England vacation. Eat fresh seafood, stop in at the Tennis Hall of Fame, and take one of the famed mansion tours.

13. August (part III): Cancun, Mexico

Plan a trip to Nizuc. This hotel will change the way you look at Cancun. I spent a long weekend here and loved it. The accommodations were top notch and all of the hotel’s many restaurants were so good. I got some tennis in on Nizuc’s private and lighted courts. The icing on the cake is that Nizuc is only a ten-minute drive from Cancun’s airport (you'd never believe it).

14. September: US Open Tennis in New York, New York
I love championship tennis, especially when you get invited to watch it with Emirates. They are the title sponsor of the US Open and accordingly have some luxury digs at the Arthur Ashe Stadium. Regardless of how you go, the US Open is iconic New York and is a who’s-who of the local scene. It's easily reached by the subway, so there are no excuses to not go.

15. More in September: Tofino and Vancouver Island, Canada
My most pleasantly unexpected destination of the year was Tofino. This is a place that not many have heard of, but once Tofino gets underneath your skin you’ll be clamoring to get back. If you have the budget, combine a stay at the Wickininnish Inn with one at Clayoquot Wilderness Retreat. There are also some great house rentals and B&B opportunities that are affordable and deliver high value.

16. October: San Francisco, California and the Blue Angels
I love San Francisco in October and when the Blue Angels come to town, the city is the perfect backdrop. There are not many airshows where the setting is such a compliment to the show.

17. Later in October: Bermuda
Bermuda is only a one-and-a-half hour flight from New York, but the island is the antithesis of Manhattan. Bermuda is gearing up for the America’s Cup sailing race and in October hosted the Louis Vuitton World Series of Racing. Even without a day of wind, we were still able to get an inside look at the world of sailing, and the setting couldn't have been better. Now is the time to head to Bermuda.

18: November: Marrakesh, Morocco and the High Atlas Mountains
I came for a travel conference, PURE, and stayed for the majestic mountains. Marrakesh is a bustling city with more than its fair share of top-notch hotels. We were privileged enough to stay at the Royal Mansour. If you want to live like a king, then stay there. We then spent time in the High Atlas Mountains, which are only a 90-minute drive from Marrakesh. If you want an authentic and local feel, stay at the Kasbah du Toubkal and pair it with a stay in their mountain lodge, which is a 17km hike away. For a more luxury option, Richard Branson also has a high-end Kasbah called Tamadot.

19. Later in November: Lausanne, Switzerland
I was invited to speak at the Leading Hotels of the World Convention, which brought me to Lausanne. It is the hospitality capital of the world with two of the world’s top hotel management schools. And the setting is spectacular. It's situated right on the shores of Lac Leman (ie Lake Geneva). The beautiful thing about Switzerland is how well connected all of its towns and cities are—Lausanne is only an hour from Geneva by train. 

20. End of November: Vienna, Austria

Hotel Sacher
I celebrated my birthday and Thanksgiving in this regal city with dear friends, two of whom are local. Our stay at the Hotel Sacher was one of my most memorable hotel stays of the year. Their suites are spacious and well appointed, the location is central, and most important, the team treats you like family. I loved walking the Christmas markets while drinking hot wine. We had great meals at hip Motto and Do & Co., the extremely local Heuriger Schmidt, as well as at Plachutta's Gasthaus zur Oper. Shopping is top notch with family-owned innovative legacies like Scheer and Mühlbauer. To top it off, we experienced the Vienna Philharmonic live.

20. December: Paris, France
After the terrorist tragedies that occurred around the world in November, I thought it was important to take a stand against the fear that terrorist acts try to strike in our hearts. It is times like these when the citizens of terror-stricken cities need us most. And so I traveled to Paris to show my support as well as to take a stand. The luxury hotels of Paris are hurting, so it’s a buyer’s market. That combined with the weak euro means it’s time to visit. Maybe that's how you can kick off your own year of travel in 2016.

>>Next: The 10 Best Travel Instagrams of 2015