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The Best Sailboat Rentals Near Sleepy Hollow
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Sleepy Hollow
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$225-$3,250
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$220-$2,915
Fishing Charters
Let a captain do the driving while you do the fishing
$100-$500
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$100-$300
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$160-$780
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50
Top Sailboat Rental Locations Near Sleepy Hollow
Recent Reviews in Sleepy Hollow
PP
PARNAZ
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Captan Rick's boat trip was an incredible experience that I highly recommend ! The planning was flawless, offering a perfect blend of activities. Captan Rick excellent communication and warm demeanor made the journey even more enjoyable. This boat trip is a must-do for anyone looking for an unforgettable day on the water!
KB
Keisha
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
The boat is large enough to comfortably fit a group of 10. We learned some new terms and had a sailing lesson. Capt Rick is a great vibe and fits right in with the group from kids to adult, the experience was one of a kind. Boat is very well kept and has lots of lounging areas inside and outside.
DE
Desireé
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Captain Rick was excellent!!! He is a skilled and patient captain. We had so much fun on the trip. Lots of laughs and great conversations. This day could not get any better. The boat and amenities were as advertised. I will definitely book this trip again with Captain Rick!
Brooke
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Capt. Rick was so fun! His knowledge of sailing and expertise made him a wonderful guide. Plus he is so personable! You can tell he really enjoys the water and loves to share the joys of being on the water with his guests! The boat was great and well outfitted! Such a wonderful experience!! I highly recommend! The trip on Capt. Ricks boat was so memorable and special! It made my 40th birthday an event to remember!
Denis
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Rick was amazing and his boat was perfect for a larger group. He offered us an amazing time and great hospitality. We shared many laughs and many great stories. I would recommend it for anyone and you could not pick a better host. The boat was capable of hosting a party of 8-10 comfortably with plenty of room to lounge and take in the sun. Super clean and super well kept. He also offers several great historic pieces about the area and don’t forget to ask him about the jacuzzi!!!
AF
ASHLEY
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Rick was passionate about his love for the water and for the art of sailing, he answered the questions the kids had, he even answered mine. He was great with the kids, pirate flags and buried treasure had them engaged from the start. The boat was incredible, the ride was comfortable and Rick was warm and inviting. I highly recommend sailing with Rick.
Top Sailboat Rental Locations in the United States
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
Real reviews from happy Getmyboaters.
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