By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
Page 3 of 39 • 914 listings
847
Miami
Florida
674
Cancún
Quintana Roo
490
Isla Mujeres
Quintana Roo
372
Tampa
Florida
362
Los Angeles
California
349
Lake Michigan
United States
322
Puerto Vallarta
Jalisco
302
Miami Beach
Florida
289
Chicago
Illinois
288
Nuevo Vallarta
Nayarit
276
Cabo San Lucas
Baja California Sur
273
Marina
Cabo San Lucas
249
Saint Petersburg
Florida
240
Tampa Bay
Florida
232
Clearwater
Florida
230
Marina Vallarta
Puerto Vallarta
225
Cartagena
Bolivar
209
Chesapeake Bay
United States
KD
Katherine
We had an amazing time sailing with Dom! The views of the Toronto skyline were incredible, and we learned so much about the Toronto Islands and about sailing along the way. What we especially appreciated was Dom’s ability to make sailing feel accessible and unintimidating—he cuts through the insider language and conventions and focuses on the practical knowledge that really matters when you’re getting started. It made sailing feel much more approachable and feasible for complete beginners like us. Dom was an incredibly warm and welcoming host, and the whole experience was relaxed, fun, and genuinely informative. We also loved how easy it was to bring our own snacks and drinks. Highly recommend!
fd
frank
Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia
We had a wonderful experience sailing to the Rosario islands! Nicholas was such a kind person, easy to communicate with and organized our trip well taking care of everything. Tatiana was so kind as well. She met us at the dock and got us on board with ease. The boat was well maintained and had everything we wanted for a great day. The crew was outstanding! The captain took us to all of the areas we asked for. We wanted to stay away from the tourist areas and he knew just where to take us. His crew member took great care of everything, serving us drinks and food as well as helping us throughout the trip! We rent boats a few times a year and this experience is one of the best we have had. We highly recommend!!!
MH
Michaella
Luxury Tripp 43 Sailboat Charter in San Francisco Bay
Dan was amazing! I couldn’t have asked for a better experience for my birthday. He gave us lots of options on routes to take and was very knowledgeable. I felt very safe on board with him and would recommend him to anyone!

Kim
Dominic was incredible! He was so chill and so kind with our family. It was a perfect day out sailing on the water. He taught us so much, shared stories, local history and was genuinely so sweet with our family, taking pictures and showing us points of interest! A PERFECT EXPERIENCE AND A PERFECT DAY!
CP
Colleen
We had a fabulous afternoon sailing with Captain Dom. He was very welcoming, friendly and knowledgeable. We immediately felt safe and comfortable sailing with him. The boat was clean and very comfortable and the vibe was relaxing and chill. We enjoyed being out on the lake with the great views of the skyline. It’s a great way to unwind and spend some quality time with some family or friends. I would definitely recommend this experience and I will be booking again to sail with Captain Dom.
EC
Ehsan
We had a great night with Dom. He was very friendly, kind, and easy to talk to, and made the whole experience enjoyable from start to finish. He also took so many great photos of us, and we’ll always have those memories. We had an amazing time and would definitely recommend this tour to anyone. Thanks again, Dom!