Welcome to Carefree Boat Club of Southern Connecticut

Experience hassle-free boating in CT and NY from four premium locations! Become a member and enjoy boating without the high costs and maintenance of ownership! Carefree Boat Club of Southern CT, a family-owned and operated club since 2016, provides members with access to a top of the line fleet of boats on Long Island Sound.

Club Form for Southern Connecticut
Terms
By providing my information, I give my consent to be contacted by the company through phone calls, emails and text messages, which may include updates about my account, as well as advertising and telemarketing messages. I acknowledge that these communications may be sent using automatic dialing systems or may contain prerecorded voices. I also understand that giving this consent is not required for purchasing any products or services, nor is it required to become a member of the company.Privacy Policy.
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Your Nearest Club Location

Rye, NY USA

Rye City Boat Basin
650 Milton Rd., Rye, NY 10580 USA

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Bridgeport, CT USA

Steelpointe Harbor
10 E. Main St., Bridgeport, CT 06608 USA

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Stamford, CT USA

Crabshell Side
78 Southfield Ave, Stamford, CT 06902 USA

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Westport, CT USA

Bridge Square
21 Bridge Square, Westport, CT 06880 USA

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Unlock Boating on Long Island Sound

All members have unlimited access to our four exciting locations in Connecticut and New York. You can choose to boat from Bridgeport, Westport, Stamford and Rye. This variety of locations allows members to experience different waterways and local waterside attractions.

Boating Made Easy and Accessible

Carefree of Southern CT maintains the highest availability in the industry by keeping its member to boat ratio at seven full memberships to one boat. Get the boat you want, when and where you want it, with our online reservation system and spur of the moment usages.

Our Fleet

Carefree Boat Club offers a diverse fleet of premium, professionally maintained vessels to meet your every boating need. Whether you're planning a relaxing cruise, a fishing trip, or a day of watersports, there's a boat for every adventure. Our fleet is regularly updated and inspected to ensure a safe, comfortable, and high-quality boating experience every time.

We make boating easy.
You make it unforgettable.

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Pontoons, Center Consoles, Deck Boats, and more

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Access to 146 locations across North America

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Unlimited on-the-water boat training

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We take care of maintenance, repairs, cleaning, & insurance

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Boats are cleaned, fueled, and ready to go

What Our Members Say

“I love the variety of boats. We’re lucky to live near some of the most beautiful waters in the world, and we get to enjoy them in all these different ways. I even tried tubing, which I never thought I’d do!”

Jess, Stuart, FL

“I will never forget the smile on my grandson’s face when he caught his first bass. It’s a memory I will cherish forever. Thank you Carefree Boat Club for creating this moment for us.”

Gordon, DMV

“Every reservation feels VIP. The Carefree Team don’t just know my name, but also the names of my wife and kids. The boat’s ready when we turn up – we just jump in and go. 100% recommend.”

Paul, Tennessee

“I have boated my entire life, and nothing compares to the ease of Carefree Boat Club. No Maintenance, no slip fees, no cleaning. It’s been a game-changer for me and my family.”

Peter, New England

“Our weekends have been transformed since we joined Carefree. No more lounging around the house looking at screens. We book a boat, head down to the dock, and enjoy some great family time together.”

Nicole, California

How Carefree Boating Works
Easy as 1, 2, 3!

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Step 1

Reserve Your Boat

Book your next adventure effortlessly—online or by phone. Choose your preferred boat, time, and location, and get ready for a hassle-free day on the water.

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Step 2

Pick Up & Go

Arrive at the dock to find your boat waiting, fueled, and ready to launch. No prep, no stress—just step aboard and set sail.

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Step 3

Enjoy

Make unforgettable memories on the water, then bring the boat back when you're done. No cleaning, no maintenance — just carefree fun. We’ll handle the rest.

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Boating Simplified. Experiences Amplified.

We believe boating should be effortless and accessible to all. Whether you’re cruising with family, casting a line with friends, or simply soaking up the serenity of the water, we want everyone to enjoy the wonders of being out on the water.

Step aboard any of our meticulously maintained vessels confident in your training and excited to make the most of the day ahead, knowing that all the boring bits of boating are being taken care of for you. Just head out, and have your best day yet!

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Hours NOT spent by our members cleaning, maintaining or winterizing their boats!

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Boat Club Locations Worldwide

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Members

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Total Boat Trips

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Boats Available

With a Carefree Membership, You Get:

Enjoy all the benefits of boating for a fraction of the cost, with membership priced at approximately one-third of traditional ownership, giving you access to a premium fleet without the hassles of maintenance, docking, or insurance.

Boat as often as you’d like - with no extra fees and no hassle. Use our online reservation system to choose the day, time, boat, and location that fit your plans. Our dock staff takes care of all the prep, cleaning, and maintenance, so your boat is ready and waiting whenever you are.

As a member, you get unlimited access to a diverse fleet of 18’ to 28’ powerboats -center consoles, pontoons, cruisers, deck boats, and more. Whether you're fishing, tubing, cruising with friends, or heading to your favorite dockside restaurant, we have the perfect vessel for you.

With our rolling reservations program, you can hold up to four bookings at a time, up to six months in advance. You’ll also have access to Spur-of-the-Moment reservations, giving you the flexibility to take out any available boat for a last-minute outing. Plus, our strict 10:1 member-to-boat ratio ensures excellent availability.

Our members enjoy exclusive access to more than 150 locations on some of the most spectacular waterways in the world. Whether you're cruising the coast or navigating scenic rivers and lakes—at home or on vacation - Carefree Boat Club gets you on the water in the most stunning destinations.

At Carefree Boat Club, every member begins with a NASBLA-certified boating safety course to ensure a strong foundation. From there, you’ll receive personalized, one-on-one training on the water - followed by specialty vessel instruction to prepare you for our entire fleet. Optional ongoing training is always available, so you can continue building confidence at your own pace.

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Ready to be Carefree?

Select Your Location to Get in Touch

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View Our Locations Worldwide

North America

Central America

Caribbean