Everyone has a different love (and appetite) for travel. Some prefer the beach, some prefer the mountains.

I can’t decide. I live in Chicago, which doesn’t make a whole lot of sense for someone with a love for mountains and temperate weather. It does, however, create a unique environment for exploring city, beach, and forest (relatively close) all at once, with a full dose of all four seasons.

Yes, it sometimes bothers me it snows nine inches overnight in March. Yes, it sometimes bothers me it hits 95 degrees in July at 80% humidity. 

But yes, it IS amazing to jump off a sailboat into the Play Pen on one of those days (which makes it ALL worth it). It still feels good to drop a paddle board into the lake in early February, just for fun.

I think I’ve decided I like returning back to this concrete jungle with intermittent trips to both the beach and the mountains. I love the energy of a big city (especially New York City) - it encourages, motivates, and drives you to excel. It’s electric, well into the early hours of the morning.

But there is something about the stillness of a night spent camping in the mountains, where the only lights you need are those from the moon overhead. There is a tranquility to hearing waves crash outside your hammock as you nap in the late afternoon. I love to snowboard and surf, which attract me to these places even more.

Many view travel as an “escape.” It’s funny how many times you hear, “Back to reality tomorrow…”

Every second you spend breathing is reality. Life, going on all around you, whether you’re on vacation or in the “real world,” is reality. Your reality is negotiable - you could live exactly where you just vacationed to. 

If you’re using vacation as an escape, maybe it’s time to take a second look at what it is you’re escaping from. I actually don’t love the term “vacation.” It creates a negative mental association with returning back home. I like "adventure." I’m changing my environment to experience something different, gain a new perspective, and expand my boundaries.

You can learn to find value in your destinations, both at home and on trips. You can take the mindful, relaxed lessons you learn on trips and apply them at home. 

Take a day off from work. Go out for a morning walk while you take your first conference call. Take two weeks off and “live” somewhere else. If you’re fortunate enough, live in multiple destinations.

My Favorite Destinations (I’ve Been To…So Far)


Interlaken / Lauterbrunnen, Switzerland - I’m an adventure sport junkie. Any gravity-aided (or gravity-resisted, if we’re rock climbing) sport is good enough to make me happy. Mountain bike riding, trail running, canyoning, you name it. This is the mecca.

Jackson Hole, Wyoming - Snowboarding is one of my favorite hobbies. JHMR is steep, deep, and enough for anyone to have the best ski trip of their life. Snowmobiling in Yellowstone, which was an amazing day trip as well.

Vail, Colorado - I’m not sure whether I enjoy the summer or winter more in Vail, but it never disappoints. Rip the bowls on a powder day, fly the groomers on a blue bird day, and enjoy long mountain bike rides during a summer day. Plus, apres is always going for winding down (or turning up).

Whistler, Canada - The “perfect” mountain, both in winter and summer. The drive up through British Columbia’s amazing wilderness is almost just as amazing.

Beaches & Islands

Kauai, US - Kauai might be my favorite place on earth. I stayed in Poipu on the southern coast, but got to adventure along the Nepali coast both by boat and by helicopter (take the open door helicopter tour, for sure). Surf, hike, snorkel, and just live.

Pebble Beach, California - My favorite stretch of coastline in the world. A mix of rocks, ocean, sunshine, and cypress trees make for an unforgettable landscape. Put a golf course right along it, and it makes for a pretty special experience.

Exuma, Bahamas - If you imagine the perfect sandbar, with nothing or no one else in sight, this is it. The water is clear, the pigs and dolphins are friendly, and Chat 'N’ Chill serves up the freshest conche salad and island cocktails.

Greek Islands, Greece - I lived on a sailboat for 7 days and sailed to a new island every day, sleeping on the boat in the harbor every night (with 70 of my closest friends). The people, food, and blue water are pretty much all you could ask for.

Tamarindo, Costa Rica - The picturesque surf town. Relaxed, amazing vibe and warm waves to get in, every day.

Nice, France - Romantic adventure through the south of France. I also made a stop in Cannes (during the film festival), which was really enjoyable.

Maui, US - My favorite golf course in the world (shhh, don’t tell Pebble), plus Mama’s Fish House, my favorite restaurant in the world. The best day ever.


New York City, New York - If you need a dose of motivation, inspiration, or flurry of activity, Manhattan is the perfect weekend trip.

Rome, Italy - The best plate of pasta, my favorite place to have a cup of coffee, and the home base of civilization. An amazing place to simply walk around.

Barcelona, Spain - Spain operates on my body clock - nap, eat late, stay up late, wake up early. Beaches, night life, soccer, and good food. Yes, please.

Amsterdam, Netherlands - Lay in the park, take a few long bike rides, and enjoy a beautiful and artistic city.

Travel light. Travel long. Travel free.

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