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Great sailboat rentals near Westbrook, Connecticut.

4.9(Average of 4,090 reviews in this area)
View our Westbrook sailing boating guide
1 - 24 of 240 listings
Charter 36ft Sloop In Westbrook, ConnecticutSailing in Westbrook6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$145person
Charter on 50ft Beneteau Sailing Yacht in Greenport, New YorkSailing in Greenport6 guests

Charter on 50ft Beneteau Sailing Yacht in Greenport, New York

5.0
$275hour
Sail the Thimble Islands on the classy 35' Dufour 4800 SailboatBranford6 guests

Sail the Thimble Islands on the classy 35' Dufour 4800 Sailboat

5.0
$200hour
Hobie One 12 Sailboat for rent in Sag HarborSailing in Sag Harbor3 guests

Hobie One 12 Sailboat for rent in Sag Harbor

New
$179day
Hunter 170 Sailboat with Honda motor in Sag Harbor, New YorkSailing in Sag Harbor6 guests

Hunter 170 Sailboat with Honda motor in Sag Harbor, New York

New
$193hour
35ft Dufour 4800 Sloop Boat Charter in Sag Harbor, New YorkSailing in Sag Harbor6 guests

35ft Dufour 4800 Sloop Boat Charter in Sag Harbor, New York

New
$300hour
42' Catalina Sailing Yacht in the Hamptons - 4 HoursSailing in Sag Harbor6 guests

42' Catalina Sailing Yacht in the Hamptons - 4 Hours

5.0
$300hour
42' Catalina Sailing Yacht in the Hamptons - 3 HoursSailing in Sag Harbor6 guests

42' Catalina Sailing Yacht in the Hamptons - 3 Hours

New
$300hour
A Large, Comfortable and Spacious Luxury Sailing Yacht in Sag HarborSailing in Sag Harbor12 guests

A Large, Comfortable and Spacious Luxury Sailing Yacht in Sag Harbor

5.0
$600hour
Large Modern Luxury Down-east Schooner Perfect for Private Sails and EventsSailing in Sag Harbor41 guests

Large Modern Luxury Down-east Schooner Perfect for Private Sails and Events

5.0
$1,150hour
Viking Princess s65 Motor Yacht Rental in Fishers Island, New YorkEvents in Fishers Island12 guests

Viking Princess s65 Motor Yacht Rental in Fishers Island, New York

New
$1,800hour
Able Custom 42' Chartered Sailing Experience in Stonington, CTSailing in Stonington3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$215hour
40' Sailing Catamaran for charter in MontaukSailing in Montauk8 guests

40' Sailing Catamaran for charter in Montauk

New
$300hour
22ft Catalina Daysailer Boat Rental in Montauk, New YorkSailing in Montauk5 guests

22ft Catalina Daysailer Boat Rental in Montauk, New York

New
$145hour
Sail from Norwalk, CT - $220/HourSailing in Long Island12 guests

Sail from Norwalk, CT - $220/Hour

4.5
Superowner
$36person
Boston Whaler 17ft Center Console with Captain in Narragansett, RIPowerboats in Narragansett5 guests

Boston Whaler 17ft Center Console with Captain in Narragansett, RI

New
$100hour
4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!Sailing in North Kingstown6 guests

4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!

5.0
$175hour
Sail From Northport or Huntington, NY - $215/HourSailing in Long Island12 guests

Sail From Northport or Huntington, NY - $215/Hour

5.0
Superowner
$50person
Charter Sailboat Cruiser in Stamford, ConnecticutSailing in Long Island6 guests

Charter Sailboat Cruiser in Stamford, Connecticut

5.0
Best of 2021
$170hour
Fast and Comfortable Sailing in Narragansett Bay and Beyond with Captain Peter!Sailing in Jamestown6 guests

Fast and Comfortable Sailing in Narragansett Bay and Beyond with Captain Peter!

4.7
$200hour
Sailing in Newport onboard Catalina 320 Sailboat with Captain Kenneth & Captain PerrinSailing in Newport6 guests

Sailing in Newport onboard Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
$150hour
42ft J Boat Sailing Yacht in Newport, Rhode IslandSailing in Newport4 guests

42ft J Boat Sailing Yacht in Newport, Rhode Island

5.0
$260hour
Pursuit 32 DC - The Ultimate Family Day Charter in Newport, Rhode IslandEvents in Newport10 guests

Pursuit 32 DC - The Ultimate Family Day Charter in Newport, Rhode Island

New
$3,500day
50 ft Sail Yacht with Young & Fun Crew :)Sailing in Newport6 guests

50 ft Sail Yacht with Young & Fun Crew :)

5.0
$250hour

Top Destinations Nearby

Sailing Reviews in Westbrook

  1. 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 ⭐️ !

  2. Seth
    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

  3. 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.

  4. 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!

  5. 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

  6. 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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