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Hotel developer Dick Friedman on the Dalai Lama’s unique laugh, Martha’s Vineyard, and packing light

Dick Friedman (on the right in the yellow vest) with world champion skier Marc Girardelli at a charity ski event in Aspen in 2022.Handout

He may be in his 80s, but real estate mogul and hotel developer Dick Friedman isn’t slowing down any time soon. The former ski racing competitor and Harvard University ski coach still likes to hit the slopes, travel the world, and go horseback riding on Martha’s Vineyard, a place he began visiting as a child and where he has owned property (now containing several homes) since 1982. “The Vineyard is special to me because I love the ethnic diversity of the people there, and I love the locals,” said Friedman, who famously hosted President Bill Clinton and his family on the island for many summers, and is friends with numerous island celebrities, including Larry David. “My older son is a tuna fisherman and an oyster farmer. He lives [on the island] full-time with the two grandkids. It’s one of the great places in the world, really. It’s a spectacular place. The only time I don’t like to go there is in August. It’s crazy.” The 83-year-old Brookline native, who is the developer behind many luxury hotels around the world, including the Liberty Hotel, the Charles Hotel, and the Four Seasons Hotel & private residences at One Dalton, which — at 742 feet and 61 stories high — is the tallest residential building in New England. He also developed, with partners the Reykjavik EDITION, Iceland’s first five-star hotel, and is working on his next project, a Four Seasons Hotel in Dallas. A former Cambridge resident, Friedman lives at One Dalton with his wife, Nancy Klemm. In addition to their Boston and Vineyard homes, the couple has a home in Aspen, Colo. We caught up with the father of two adult sons and two granddaughters to talk about all things travel.

If you could travel anywhere right now, where would you go? I haven’t been there in quite a while, but I would love to go back to Bhutan. It is a beautiful and peaceful place in the Himalayas, where they believe in a Gross National Happiness index. Sicily is another place I’d like to visit again soon.


Where was the first place you traveled to after COVID restrictions were lifted? I frequently traveled to Iceland because I was building the Reykjavik EDITION Hotel up there. For many months I was one of the only passengers on the plane, except for the fish they were shipping to the US.

Do you prefer booking trips through a travel agent or on your own? I plan my own travel itinerary but book trips through Diamond Air International, a VIP meet-and-greet service available through American Express Centurion. It’s a terrific benefit that makes every aspect of travel ― from departure through arrival ― smooth and efficient, especially figuring out customs in unfamiliar airports.


Thoughts on an “unplugged” vacation?

Unplugging can be tough given my schedule. But I do unplug when in the backcountry, [helicoptering] and powder skiing — or fishing in exotic places.

Do you use all of your vacation time or leave some on the table?

When it comes to vacations, I’m very lucky. Because of the nature of my work as a developer of hotels, work and travel are often combined. My business takes me across the country and around the world.

What has been your worst vacation experience?

I remember an awful trip to Costa Rica with my wife and my kids. Let’s just say the hotel did not live up to its reputation. And I was terrified of its less-than-reliable-looking zipline in the jungle. I also had a horrible Christmas/New Year’s trip to Egypt a long time ago which was a nightmare from the beginning, as I was traveling with several other couples and one very famous person had promised to take us on his private jet — which he didn’t have.


Do you vacation to relax, to learn, or for the adventure of it all?

All of the above.

What book do you plan on bringing with you to read on your next vacation?

Walter Isaacson’s new biography of Elon Musk. Given that it’s almost 700 pages, it will take me more than one trip to finish.

If you could travel with one famous person/celebrity, who would it be?

His Holiness the Dalai Lama. I have known him quite well for a long time and he is an unbelievable person to be around. There’s an aura about him that is spectacular — and he’s very funny with a very strange laugh; he laughs on the inhale.

What is the best gift to give a traveler?

An Ambien.

What is your go-to snack for a flight or a road trip?

I drink sparkling water to stay hydrated. On long flights, I usually travel at night, so I try to eat dinner immediately after takeoff so I can get some sleep. The food is bad and since it’s always much better where I am going, I’d rather sleep.


What is the coolest souvenir you’ve picked up on a vacation?

I like to buy leather goods, ties, and shoes in Italy. I also collect Tibetan conch shells, decorative horns that are used as musical instruments in Bhutan as part of religious rituals and by shepherds tending their flocks.

What is your favorite app/website for travel?

Airline ticket prices can significantly change, so I always check Google FlightsPrice Graph for the best options, which sometimes vary wildly in price from one day to the next.

What has travel taught you?

I’ve learned that there are interesting people everywhere and that you can learn a lot about a place by talking to locals, whether it’s a taxi driver, waiter, a shop owner, or a museum guide.

What is your best travel tip?

Travel light. You don’t need all the stuff you think you need. That’s why I only take a carry-on bag — saves lots of time and gets me out of the airport and to my destination faster.

Juliet Pennington can be reached at