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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-$465
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$70-$355
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$80-$130
Kayaks
Who says you need a motor to have fun on the water?
$250-$290
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$110-$140
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$160
Fishing Charters
Let a captain do the driving while you do the fishing
$115
Top Sailboat Rental Locations Near Whitby
Recent Reviews in Whitby
FS
FRANCI
Sailing NYC aboard 34' Catalina
Ian provided us with a fantastic sailing experience for our wedding anniversary. It was absolutely lovely—truly beyond our expectations. His communication and instructions were clear and outstanding from start to finish. On the day of our sail, Ian even reached out to offer an earlier time slot when one became available, which we appreciated. The boat was perfect, and we had an unforgettable time on the water. Thank you, Ian, for making our special day even more memorable!
Irina
35ft C&C 35 Sailboat in Toronto
It was a great experience for me and my whole family. Peter made us a part of sailing experience and my husband and our teenagers gladly participated in everything that needed to be done and also enjoyed the conversation and the company of the captain. Thank you, Peter!
Abhishek
The Only 40ft Hinckley Sailboat in Manhattan
Captain Andy is one of the best hosts and extremely skilled at what he does. I was planning a proposal for my girlfriend and he went above in beyond in helping us out. He gets back quickly regarding any queries and makes sure you have a memorable experience. I have nothing but good this to say about our experience. Definitely recommend Captain Andy if you are looking for a good time on a sail boat.
AM
Angela
Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Wonderful experience with my 2 daughters! They jammed out to their favorite music while enjoying the sights and were given a chance to steer the boat! Ian was attentive and amiable throughout the booking and sailing experience.
AS
Andie
Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Ian and Kim were fantastic hosts, captain and first mate! We used Ian’s vessel for a music video shoot, and not only were they helpful and accommodating, but happy to have us aboard and a part of our production. I highly recommend booking with Ian for a similar situation or if you just wanted a fun outing with some good friends!
Miss
35ft C&C 35 Sailboat in Toronto
I need just one word to describe this experience! - Incredible ! 🤩🤩
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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