Florida Keys Sailing Trip

Enjoy two weeks of swimming, snorkeling, sunning and sailing.


Florida Keys Sailing is a must for those who love the sun, marine life, water, the open ocean, and sailing. Join the Camp T Trippers for one of the most adventurous experiences camp has to offer. Begin by trekking to the southern most point of the United States – Key West. Along the way, enjoy road tripping Camp T style, learning the ins and outs of low impact camping, discovering secret tripper traditions, and even wind-surfing off the beaches of Miami for a day-long excursion.


After setting sail off Little Torch Key, trippers will get the full experience of sailing the 74’ steel schooner – the Dream Catcher. Under the direction of Captain John Duke, trippers will sail for 5 days throughout the Florida Keys stopping at only the most surreal locations (see one journal entry below!). As part of the crew, you are responsible for cooking, cleaning, setting sail, sailing, anchoring, rowing the long-boat Aida, and even swabbing the deck.


Florida Keys Journal Entry


“The next five days were an experience that none of us will ever forget. We were able to snorkel around the outskirts of a coral reef, among a haven of barracuda, and again around an old sunken ship. We anchored for a few days in the Marquesas, a national refuge, and were able to walk the beach, swim in the beautiful, tropical water, and see the nests of giant sea turtles. We also sailed to Boca Grande, where we walked another beautiful beach and took turns diving off the bow of the boat. We saw nurse sharks, jellyfish, all varieties of fish, and on several occasions we saw families of dolphins.


Every morning, noon and night we were able to take two-seated kayaks out to explore the surrounding waters. We learned about raising and lowering main sails, hoisting the jib, and how to row a longboat. Several of the girls even took the opportunity to learn how to steer the Dream Catcher. Captain John Duke spent some time one afternoon teaching us how to read a navigational chart, and explaining some of the history of the area where we were sailing. All throughout our time on the boat, we prepared incredible meals in the ship’s galley. A few of the most memorable On The Boatmeals included crepes, pancakes and bacon, grilled pineapple, barbecued chicken, chili dogs, spaghetti with Italian sausage, and Mexican burritos. Basically, we ate like kings!


Every night we were treated to gorgeous sunsets while the dish crew washed up and then we usually played charades before gathering together for devotions. The gifts we read about on board included the gifts of family, laughter, dreams, giving, and gratitude. We loved devotion time. Tripper devotions are the best! Then we fell asleep on the deck, under a trillion stars—unless of course it was raining and we had to sleep below.”