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Great sailboat rentals near Westbrook, Connecticut.
View our Westbrook sailing boating guide1 - 24 of 240 listings
Charter 36ft Sloop In Westbrook, Connecticut
Charter on 50ft Beneteau Sailing Yacht in Greenport, New York
Sail the Thimble Islands on the classy 35' Dufour 4800 Sailboat
Hobie One 12 Sailboat for rent in Sag Harbor
Hunter 170 Sailboat with Honda motor in Sag Harbor, New York
35ft Dufour 4800 Sloop Boat Charter in Sag Harbor, New York
42' Catalina Sailing Yacht in the Hamptons - 4 Hours
42' Catalina Sailing Yacht in the Hamptons - 3 Hours
A Large, Comfortable and Spacious Luxury Sailing Yacht in Sag Harbor
Large Modern Luxury Down-east Schooner Perfect for Private Sails and Events
Viking Princess s65 Motor Yacht Rental in Fishers Island, New York
Able Custom 42' Chartered Sailing Experience in Stonington, CT
40' Sailing Catamaran for charter in Montauk
22ft Catalina Daysailer Boat Rental in Montauk, New York
Sail from Norwalk, CT - $220/Hour
Boston Whaler 17ft Center Console with Captain in Narragansett, RI
4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!
Sail From Northport or Huntington, NY - $215/Hour
Charter Sailboat Cruiser in Stamford, Connecticut
Fast and Comfortable Sailing in Narragansett Bay and Beyond with Captain Peter!
Sailing in Newport onboard Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
42ft J Boat Sailing Yacht in Newport, Rhode Island
Pursuit 32 DC - The Ultimate Family Day Charter in Newport, Rhode Island
50 ft Sail Yacht with Young & Fun Crew :)
Top Destinations Nearby
Sailing Reviews in Westbrook
- AT
April
Fast and Comfortable Sailing in Narragansett Bay and Beyond with Captain Peter!
Captain Peter was a wonderful host and guide, and the Charles Edward is a awesome catamaran - it’s huge, gorgeous and comfortable.This was my first booking through GetMyBoat, and I give the experience and Captain Peter & the Charles Edward ALL THE STARS ⭐️ !
Seth
Sailing in Newport onboard Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Kenny and Perrin were fantastic with communication throughout the process of booking and getting us out for a sunset cruise! Our family had a great time with Perrin and he is very knowledgeable about the area and has tons of experience. We felt right at home on Mariah! We will definitely be back. Great boat, great captain, and a great experience all around. Highly recommend. Seth
- HD
Harsh
Charter Sailboat Cruiser in Stamford, Connecticut
Loved the captain of the boat, Marco. Made us feel safe, showed us a fun time, had all the amenities you could possibly ask for with your loved ones. The boat was also very clean. Have no negatives.
- CM
Cindy
Sailing in Newport onboard Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Perrin was amazing! The whole process was such a breeze and we had a great couple of hours out on the water. Really knowledgeable (and we tested him haha) and had great insight about the area and the other boats around us. Would definitely recommend!
- AG
Avirat
Charter Sailboat Cruiser in Stamford, Connecticut
Marco communicated clearly about the parking and dock to get to the boat. We left on time and he explained us about the boat, sails and we put up the front sail up together. It was amazing watching the sunset on the boat. 10/10 would recommend
- TB
Tayler
Sail from Norwalk, CT - $220/Hour
Best time ever! Captain Mark was awesome! He was flexible with our docking location, quick with communication, and very knowledgeable. His boat is beautiful. 10/10 recommend. We hope to do this every year :)
Boating Guide - Westbrook Sailing
Step onboard a sailboat for an unforgettable experience in Westbrook, Connecticut.
Get ready for a fun adventure when you hit the open water onboard a sailboat in Westbrook, Connecticut. Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Westbrook, Connecticut is a wonderful sailboat rental destination.
Using GetMyBoat to rent your next sailboat.
Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.
Search for the perfect experience now and book your dream day out on the water.
GetMyBoat has 240 listings for Sailing experiences in Westbrook with 4,090 reviews.
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