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Five Miles Up: How Jay Michael designs a vacation

Bekah Wright
February 25, 2014

As Bravo’s reality series "100 Days of Summer" closes out its season, Jay Michael will most likely be eyeing vacation spots. So where might the COO/Co-Founder of FLATS Chicago find himself? He is, as his website describes him, a “Lifestyle Architect in search of the world’s best way to live.” Wherever the destination, he’ll “eat with the people, but sleep like royalty,” with healthy doses of hiking, biking and lugging copper cookware.

What’s something you never fail to pack in your suitcase?
Running gear. There’s no better way to become acquainted with a city than on an unmapped run.

Carry-on or check-in?
For leisure travel, I shamelessly check-in. It allows me to travel light on the plane, gives me room to pack for more than one climate (you never know where you may end up) and I always seem to come home with a few more things than I left with, so I need a little extra room.

Window or aisle?
Aisle – it’s easy access to everything.

What’s your idea of the perfect vacation?
Hiking or biking a desolate, beautiful and unspoiled part of the world and staying in eco-lodges ... Followed by a day or two in a big, bustling city staying in a hotel with a great spa.

Tell us about a vacation you’ve taken that’s come close thus far.
In 2012, I mountain-biked the Vietnam/China borders in a region called Sapa. It was one of the most unforgiving, difficult treks of my life, yet one of the most breathtaking and rewarding. We stayed at eco-lodges lost in mountains of rice paddies, and ate meals with families along the way. We ended the trip in Hong Kong eating dim sum, getting massages to soothe our sore muscles and sipping cocktails at an infinity pool overlooking Kowloon.

What’s the worst vacation you’ve taken?
Family Camp (Dirty Dancing style minus the beautiful mountains and music) with everyone related – or sort of related – to my family staying in one cluster of cabins.

Where’s your favorite destination for practicing your profession?
I seek inspiration all over the world. If I were to choose one spot, it would have to be London, as my creative juices just don’t stop flowing from the second I land. I find myself snapping shots from my iPhone and taking notes everywhere I end up in the city.

What's the most unusual souvenir you’ve ever brought back from a trip?
Over the holidays this year, I was in Paris and fell into E.Dehillerin, a chef store specializing in French copper. Needless to say, I left with my first pieces of copper cookware and schlepped these heavy finds through London, then Palm Springs, before finally making it home to Chicago. It was a workout.

Ever try a food you wished you hadn't?
I once had balut at a night market in northern China. Balut is a developing duck embryo that’s boiled alive and eaten in the shell, mainly at street markets in Asia. I only took a tiny bite, but that was more than enough!

Favorite hotel, resort, yurt, train, boat you've ever stayed in/on?
The Connaught, London. It’s one of my favorite splurges the world over. It’s quintessentially English with an Aman Spa tucked away below ground. What could be better than that?

Favorite restaurant you’ve discovered while traveling.
Café Bar Du Brésil in The Marais, Paris. It’s the absolute perfect marriage of bar, street café, bistro, and after-hours spot all crammed into less than 1,000 feet. Only the Parisians can successfully pull that off.

Biggest regret you've ever had while on vacation.
I almost bought a striking Helmut Newton photograph in London several years back, but it was a big price for me at the time, and I couldn’t make myself do it. That photograph has since sold at auction for more than 10 times what I would have paid for it.

The one thing you're willing to splurge on when traveling above all else.
I like to eat with the people (street food & neighborhood eateries), but sleep like royalty. I splurge on hotels and almost never on dining.

Three artists on your travel playlist?
Tim Chaisson, Mark Wilkinson and Lee DeWyze – modern country soothes me when I travel.

Where would you take someone visiting your hometown for the first time?
Vincent in Andersonville, Chicago. It’s a neighborhood eatery with fine food and a lovely ambiance, without the fuss or the pretense that’s very Chicago.

You only get one more trip in your lifetime. Where will it be?
India, for at least a month. Until I find my way there, it will remain a priority on my bucket list.