Ten Thousand Islands: Private Catamaran Sailing Tour

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Sail wild florida waters on a vintage catamaran with local captain

You’ll sail Florida’s Ten Thousand Islands on a vintage stiletto catamaran with an easygoing captain who lets you help with the sails or just kick back. Expect close-up wildlife moments, salty breezes, bottled water on board, and plenty of space to feel small in the best way.

What’s included

Your day includes two hours aboard a classic stiletto catamaran with a knowledgeable local captain guiding you around Florida’s Ten Thousand Islands, plus chilled bottled water to keep you refreshed as you sail past mangroves and wildlife.

Traveler reviews

4.89★★★★★★★★★★

156 verified traveler reviews

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fromUS$ 450 See dates & prices ›

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Step-by-step itinerary

Day 1 — Private sailing tour in Ten Thousand Islands

Board private performance catamaran
Sail around Ten Thousand Islands
Captain points out flora and fauna
Help man the sails or relax

★★★★★★★★★★

4.89

(156 reviews)

The Experience

“You ever seen dolphins up close like this?” our captain asked, just as something sleek broke the surface near the bow. I was still figuring out how to sit without sliding around (those stilettos are fast — nobody warned me), but I managed to spot the fin before it disappeared. The Ten Thousand Islands looked endless from the water, all tangled mangroves and little spits of sand, and honestly, I’d never felt so small in such a good way. There was this salty breeze that kept my hair in my mouth no matter what I did, but it just made everything feel more real.

The stiletto catamaran itself was kind of a character — built in the 80s, our guide told us, and apparently famous among sailors for being quick and dry. He let us help with the sails (“just pull here — not too hard!”), which was both exciting and slightly terrifying since I have zero upper body strength. At one point I tried to say “thank you” in his accent and got laughed at (deserved). We drifted past these weirdly beautiful clusters of birds and he pointed out some plant whose name I immediately forgot. There’s something about being out there — you start noticing tiny things, like how quiet it gets when the wind drops for a second.

I brought my own snacks but mostly just drank the cold bottled water they handed out — sun does funny things to your appetite. We saw maybe two other boats the whole time, which made it feel like we’d lucked into our own private world. If you’re thinking about booking this private sailing tour through the Ten Thousand Islands, just know: you’ll probably get sandy feet and windburned cheeks and still not want to go back in.