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The Best Sailboat Rentals Near Chester
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Chester
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$185-$905
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$150-$400
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$65-$350
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$195-$260
Fishing Charters
Let a captain do the driving while you do the fishing
$95-$350
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$350
Kayaks
Who says you need a motor to have fun on the water?
$65
Top Sailboat Rental Locations Near Chester
Recent Reviews in Chester
DD
Danuta
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
What an enjoyable experience! Captain Joe was always attuned to our wishes, making an extra effort to make this afternoon pleasant for all. His company is very agreeable. We wish we could relive yesterday's feeling of complete relaxation over and over!
ST
Sherzod
38-ft Hunter 376 Sailing Adventure in Annapolis
Great experience, it was my first time boat sailing and Alberto and his wife were great. My fiance and I had a great time. Highly recommend!
BF
Bruce
38-ft Hunter 376 Sailing Adventure in Annapolis
Our family of four, who are experienced sailors, appreciated the opportunity to sail with Alberto and his lovely wife, who shared lots of great stories and reflections of sailing on the Bay. The boat was perfect for a day of sailing, and exactly how described on the website. It was clean and comfortable and we felt completely welcomed, and were able to participate in sailing activities as we desired, while also relaxing and enjoying some downtime. Great time sailing!
SW
Stacie
38-ft Hunter 376 Sailing Adventure in Annapolis
Our sailing trip exceeded our expectations! Captain Alberto is a complete treasure: he shared his sailing knowledge and involved us in the sail as much as we wanted - The boat was clean and comfortable with space to enjoy the trip both above and below deck. We only had 2 in our party, but 6 people would absolutely be comfortable given the space. We hope to book a trip with Capt. Alberto again!
Cliff
38-ft Hunter 376 Sailing Adventure in Annapolis
I found Captain Alberto and his first mate lovely wife were the ultimate hosts and storytellers. What I didn't expect, was to get impromptu sailing lessons. It was a beautiful day on the Chesapeake and I would highly recommend this to anyone who wants to truly appreciate the beauty and magnificence and physics of sailing
AM
Aleisha
38-ft Hunter 376 Sailing Adventure in Annapolis
BOOK WITH CAPTAIN ALBERTO!! I mean this was the BEST thing experience I had all summer. He accommodated our needs, let us have fun, and taught us soo much during the process. Captain Alberto just had the best hospitality that I’ve seen in a long time. As a first-time boat goer, he made me feel so comfortable and welcomed! I will definitely be back and will rebook with captain Alberto. I mf you are looking through boat options and stumble on this, this is your sign to book with him!
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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