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All listings in Westbrook

Great sailboat rentals near Westbrook, Connecticut.

4.9(Average of 4,371 reviews in this area)
View our Westbrook sailing boating guide
24 listings
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$145person
Charter on 50ft Beneteau Sailing Yacht in Greenport, New York
Sailing in Greenport · 6 guests

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

5.0
$275hour
Sail the Thimble Islands on the classy 35' Dufour 4800 Sailboat
Branford · 6 guests

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

5.0
$200hour
Hobie One 12 Sailboat for rent in Sag Harbor
Sailing in Sag Harbor · 3 guests

Hobie One 12 Sailboat for rent in Sag Harbor

New
$179day
Hunter 170 Sailboat with Honda motor in Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

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

New
$193hour
35ft Dufour 4800 Sloop Boat Charter in Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

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

New
$300hour
42' Catalina Sailing Yacht in the Hamptons - 4 Hours
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 4 Hours

5.0
$300hour
42' Catalina Sailing Yacht in the Hamptons - 3 Hours
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 3 Hours

New
$300hour
A Large, Comfortable and Spacious Luxury Sailing Yacht in Sag Harbor
Sailing in Sag Harbor · 12 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 Events
Sailing in Sag Harbor · 41 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 York
Events in Fishers Island · 12 guests

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

New
$1,800hour
Able Custom 42' Chartered Sailing Experience in Stonington, CT
Sailing in Stonington · 3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$215hour
40' Sailing Catamaran for charter in Montauk
Sailing in Montauk · 8 guests

40' Sailing Catamaran for charter in Montauk

New
$300hour
22ft Catalina Daysailer Boat Rental in Montauk, New York
Sailing in Montauk · 5 guests

22ft Catalina Daysailer Boat Rental in Montauk, New York

New
$145hour
Sail from Norwalk, CT - $220/Hour
Sailing in Long Island · 12 guests

Sail from Norwalk, CT - $220/Hour

4.5
Superowner
Best of 2022
$36person
Boston Whaler 17ft Center Console with Captain in Narragansett, RI
Powerboats in Narragansett · 5 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 Kingstown · 6 guests

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

5.0
$175hour
Sail From Northport or Huntington, NY - $215/Hour
Sailing in Long Island · 12 guests

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

5.0
Superowner
Best of 2022
$50person
Charter Sailboat Cruiser in Stamford, Connecticut
Sailing in Long Island · 6 guests

Charter Sailboat Cruiser in Stamford, Connecticut

5.0
Superowner
$170hour
Fast and Comfortable Sailing in Narragansett Bay and Beyond with Captain Peter!
Sailing in Jamestown · 6 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 Perrin
Sailing in Newport · 6 guests

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

5.0
$150hour
42ft J Boat Sailing Yacht in Newport, Rhode Island
Sailing in Newport · 4 guests

42ft J Boat Sailing Yacht in Newport, Rhode Island

5.0
$260hour
Pursuit 32 DC - The Ultimate Family Day Charter in Newport, Rhode Island
Events in Newport · 10 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 Newport · 6 guests

50 ft Sail Yacht with Young & Fun Crew :)

5.0
$250hour

Top Destinations Nearby

Sailing Reviews in Westbrook

  1. RM
    Rachel
    50 ft Sail Yacht with Young & Fun Crew :)

    I'm a photographer who hired Steve and Bec for a couples sailboat shoot. They knew exactly how to get the best angles and then treated us to an amazing view as the sunset. I can't recommend these guys enough! We had a blast!

  2. LG
    Lucas
    50 ft Sail Yacht with Young & Fun Crew :)

    Steve and Bec were awesome! My wife and I had such a lovely time. Steve is a wealth of knowledge of Newport history and lore and Bec was super friendly and made our experience amazing.

  3. 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 ⭐️ !

  4. JR
    Jai
    Sail the Thimble Islands on the classy 35' Dufour 4800 Sailboat

    We had a wonderful experience and found Captain Eric to be an excellent sailor and gracious host. He is extremely friendly, relaxed and a great conversationalist who has many stories to tell about the Thimble Islands and other topics. We had a large party with a two year old child and Captain Eric made us all comfortable and provided us with a perfect trip.

  5. Lauri
    Lauri
    Sail the Thimble Islands on the classy 35' Dufour 4800 Sailboat

    CaptIn Eric provided an amazing experience for my family. Not only did he display his professional sailing skills but he accommodated time for dining and swimming and the thrill of being under sail on a beautiful sunny and windy day. We've already shared our great experience with friends and family and hope to join them for another trip on Erics Nomade.

  6. Ilona
    Ilona
    42' Catalina Sailing Yacht in the Hamptons - 4 Hours

    We had a great day out on the water with Nate! He was very flexible with starting a bit later due to the weather and had great communication overall. He and his crew are very kind and professional. The boat is great and this is a must-do while you are in the Hamptons!

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 24 listings for Sailing experiences in Westbrook with 4,371 reviews.

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