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Dennis Claffey
Trip Guide

Dennis Claffey

Dennis grew up in Windsor Locks, Connecticut. As a child, he spent much of his time exploring the woods behind his home- building shelters and climbing trees. He attended Northeastern University in Boston, finishing with a Bachelor’s in Environmental and Marine Studies. As a member of the student outdoor club, he spent many weekends hiking, skiing, and climbing. Dennis attended the SEA semester program, where he learned to sail on a tall ship while conducting experiments at sea. 

After University, Dennis declined an office job, opting instead to somehow get back on a boat. He has spent the last six years working on superyachts and is now a qualified Deck Officer. Yachting has led him around the world, to places he never knew existed, and he can’t get enough of it! He plans to return to sea in the off-season and experience the best of both worlds- guiding national parks in the summer and navigating the seas in the winter! 


What’s your favorite vacation destination?   

Anywhere I haven’t been. So many places left to see, so little time. The South Pacific, Patagonia, and Antarctica are topping the bucket list now. 

What’s your favorite hike?

Reunion Island- a small volcanic island east of Madagascar. In the center are lush valleys, with villages only accessible by foot trails. In the villages are small “gîte” hostels where you can book a bunk and enjoy family-style French cuisine. At the heart is Piton de Neiges: a two-day ascent from subtropical forest to near alpine conditions. I camped above a sea of clouds and witnessed an incredible summit sunrise.

What’s your favorite bike ride?

Mount Haleakala on Maui. Sunrise at the top, then bike to the beach. Not the most strenuous- I didn’t have to pedal once from the summit to sea! But the scenery was incredible, and I caught some serious speed. The guide said he was once pulled over by police for speeding on a mountain bike!

Favorite movie?

The Lighthouse, starring Willam Dafoe and Robert Pattinson. Such a bizarre, beautifully filmed movie full of excellent monologues, and Dafoe invoking his best Captain Ahab. 

Favorite book?

The Hobbit and The Lord of the Rings. 

Favorite song?

Tough one. Lately, it’s been “This Must Be The Place (Naïve Melody)” by Talking Heads. 

When did you first catch the travel bug?

Sailing with SEA semester. After 6 weeks of navigating by the stars and exploring the Hawaiian Islands, I wanted to work on the water and see the world! 8 years on, I’ve visited over 20 countries, 4 of 5 oceans, and logged over 45,000 sea miles. 

What are your hobbies?

Anything outdoor and sport-related. Hiking, climbing, skiing, diving, free diving, the list goes on. I also enjoy playing guitar and piano, wood carving, and golfing. The latest hobby is pickleball. My dad discovered it recently and loved it so much he put a court in his backyard. Now, the whole family is addicted! 


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