Tailor a private Caribbean sailing charter for your celebration or getaway
Up to 6 people
Private charter, catamaran
Set sail on a private Caribbean charter designed around your vacation, event, preferred duration, and budget. Relax aboard a sailing yacht and celebrate any occasion on the water.
This booking is for the whole experience, which fits up to 6 guests.
Fully paid reservations are refundable less 30% with cancellation notice at least 6 months before your scheduled trip. Other refund requests are subject to management approval. Approved refunds are usually issued within 4 business days.
A fuel, dockage, and insurance surcharge applies and is not included in the listed price. Gratuity is also not included; a 15% gratuity may be assessed at the completion of your charter using the card on file.
Captain Brad and Maddie are the real draw here, and it shows in nearly every review. Guests consistently rave about their warmth, humor, and genuine expertise on the water. Brad handles navigation and local knowledge while Maddie keeps guests comfortable with food, drinks, and dolphin spotting tips. The boat itself, a 60-foot catamaran called Zodiac, is described as spotless and well-appointed with thoughtful touches like beanbag loungers and Bluetooth speakers. What stands out most is how personalized each trip feels. Reviewers mention proposals, birthday celebrations, holiday fireworks, and even a Bahamas sailing week, suggesting Brad and Maddie are equally comfortable with quick day sails and longer adventures. The food and drinks receive consistent praise, and the crew's attention to safety comes up often without ever feeling rigid or overly formal. With a near-perfect rating across a strong volume of reviews, this is clearly a team that takes pride in the experience they deliver.
We had a phenomenal time! Captain Brad and Maddie were absolutely incredible. Brad is such a great captain—so fun, funny, and incredibly knowledgeable about Key West. He took us to a fantastic sandbar area where we did a lazy river and just hung out; we had an absolute blast. Maddie was fabulous and so pleasant, constantly serving us delicious drinks and lunch throughout the day. The boat itself is gorgeous. It’s brand new, beautiful, and had absolutely everything we needed. We honestly felt like celebrities on a private excursion! My friends and I have been talking about it ever since, and it was easily the highlight of our trip. Thank you for a 10/10 experience! 🛥️🌴🍹
Mark Rukavina
May 17, 2026
We had a phenomenal time! Captain Brad and Maddie were absolutely incredible. Brad is such a great captain—so fun, funny, and incredibly knowledgeable about Key West. He took us to a fantastic sandbar area where we did a lazy river and just hung out; we had an absolute blast. Maddie was fabulous and so pleasant, constantly serving us delicious drinks and lunch throughout the day. The boat itself is gorgeous. It’s brand new, beautiful, and had absolutely everything we needed. We honestly felt like celebrities on a private excursion! My friends and I have been talking about it ever since, and it was easily the highlight of our trip. Thank you for a 10/10 experience! 🛥️🌴🍹
Mark Rukavina
May 17, 2026