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Sailboats
Set sail with these traditional wind-powered boats
$130-$1,155
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$160-$1,155
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$130-$250
Fishing Charters
Let a captain do the driving while you do the fishing
$130
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$130
GS
Genevieve
Private San Juan Bay Cruise 37' Sailboat
I booked with Captain Luis for my sister’s 30th birthday trip, and we all had the best experience! There were 4 of us in San Juan for a long weekend and this was the highlight of our trip. We felt safe, welcome, and taken care of the whole ride - the captain brought refreshments including Sangria that his wife had made which we all loved. He sailed us around and anchored at a beautiful spot to jump in and swim which was so fun. I highly recommend!
Tamela
Private Islamorada Charters in the Florida Keys
Dawid "David" was great! Our family chose his charter services to celebrate our dad's 70th birthday, and our expectations were exceeded. We had a blast! He's very accommodating and chill. He is an EMT and paramedic, which added an extra level of peace of mind. His price is also very affordable for the services offered. Book with him; you won't be disappointed!
GP
Gianluca
Huge! Delray Beach $339!!!*
Steve went above and beyond for my family and I this past father's day. From start to finish, the experience was exceptional. The boat was perfect for my large family of 7. We booked the trip on less than one week notice for father's day and it turned out to be the best decision we could've made. I will definitely be back to book this boat again. If you book this boat you will love it!
Marissa
Huge! Delray Beach $339!!!*
Absolutely incredible experience! Stephen was professional, knowledgeable, and truly passionate about what he does. From start to finish, everything was seamless, safe, well organized, and tons of fun. The boat was in excellent condition, and Stephen made sure everyone felt comfortable and welcome, whether it was our first time on the water or not. I can’t recommend this experience highly enough we’ll definitely be booking again. Thanks for a trip to remember!
MD
Maddie
Huge! Delray Beach $339!!!*
Captain Stephen was AMAZING! Highly recommend booking with him. We went on a 3 hr boat cruise for a bachelorette party and it was our favorite part of the whole weekend. Boat stereo system, fridges, bathrooms, top deck for dancing, and water mats to float on it was the perfect day.
Suzanne
Best Day Ever! Private, All Inclusive & Custom Sailing, Snorkeling, Adventure!
We chartered Saltwater Taffy whilst on a recent cruise to St Thomas. The 4 of us had the best time ever. Great communication from Rosie on the days before the sailing. We were met at the ship by Brad and driven to the boat where we met Rosie and Bosun the cat. We set sail straight away into turquoise waters and we were quickly under sail. We chose to snorkel with turtles so we went to Scott beach, got kitted up with snorkels and Brad took us to the beach in the motor rib. It’s really easy to get in and out of the water from the swim platform. We swam for about 10 minutes until we found the turtles. They are just so graceful. Brad got some great underwater pics. We then went back to the boat where Rosie had been preparing an amazing lunch and cocktails. We then motored back to the dock. Best day ever and we will be back to do it all over again. Thanks so much. Suzanne, Chris, Pam and Ricky xxxx
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
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Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!