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The Best Sailboat Rentals Near Whitby
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Whitby
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$115-$700
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$75-$250
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$85-$130
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$110-$145
Fishing Charters
Let a captain do the driving while you do the fishing
$120-$165
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$165
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$145
Top Sailboat Rental Locations Near Whitby
Recent Reviews in Whitby
AB
Annie
Woman-owned luxury with transparent pricing - read our 5-star reviews!
We had such a good experience with Jessica and Captain Dan! The boat was supplied with basic needs and a bathroom! There is a Bluetooth speaker and a bean bag in the front of the boat so that you can lounge there if you'd like. The communication up front was excellent and easy to follow. I highly recommend this experience. Myself and the 5 others in tow had the best time! Thank you!
MS
Megan
Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
We celebrated our 10th anniversary on Faith and couldn’t be happier. Captain Ian personalized the journey for us and guided us along the way. He was exuberant, caring, and checked in with us to make sure we were having a great time. He asked if we wanted to learn sailing and taught us a few things, which was so cool and unexpected. We are excited to sail again to learn more and see the beautiful sites NYC has offer!
MR
Matthew
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
We had a great time sailing out of Port Washington with Steven! Got to sail around the harbor to see some cool houses in Great Neck, the old lighthouse, and views of New York City in the distance. Steven was very communicative and a great captain for the morning! Would do again!
GB
Gillian
The Only 40ft Hinckley Sailboat in Manhattan
This was such a great experience. Andy was wonderful and the boat is absolutely lovely. I would highly recommend this to anyone looking to book a boat outing. It was such great value for the experience and we had a wonderful time
Cindy
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Our sailboat outing was absolutely perfect - peaceful, scenic and incredibly relaxing. The boat was pristine. Captain Charles and his wife were perfect hosts. Highly recommend!
JC
Julia
Woman-owned luxury with transparent pricing - read our 5-star reviews!
Highly Recommend!!! Jessica was very responsive and helpful with helping me plan our last minute sailing. Everything was exactly as described. The ship was clean with nice amenities for our entire party. Captain Kevin was extremely knowledgeable and provided a great experience with plenty of photo opportunities! We can’t wait to do this again!!
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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