Thank you for inquiring about Carefree Boat Club of Southern Connecticut.
We are delighted that you are interested in learning more and possibly joining our incredible club.
We invite you to join now and save up to $500 off 2025 pricing! Pay about 50% of the cost of membership now and the balance with monthly payments for 12 months starting on May 1, 2025. Your membership will be good until April 2026!
Members coming aboard before April 30th will receive discounted pricing up to $500 Plus an additional 2-Hour session of On the Water Training to brush up on boating skills before summer! Don't miss the best deal of the winter and plan on spending many sunny days on the water with friends and family next summer.
Brand-new boats were added to the fleet this fall, making room for new members at each of our 5 locations!
We invite you to join now and save up to $500 off 2025 pricing! Pay about 50% of the cost of membership now and the balance with monthly payments for 12 months starting on May 1, 2025. Your membership will be good until April 2026!
Members coming aboard before April 30th will receive discounted pricing up to $500 Plus an additional 2-Hour session of On the Water Training to brush up on boating skills before summer! Don't miss the best deal of the winter and plan on spending many sunny days on the water with friends and family next summer.
Brand-new boats were added to the fleet this fall, making room for new members at each of our 5 locations!
Our Pricing
Membership Type (annual) |
Number of Rolling Reservations*** |
2025 Pricing |
Spring Sale through April 30, 2025* |
Savings! |
12-Pak - 8 weekday / 4 weekend outings |
1 weekend - 2 weekday |
$4,350 |
$4,150 |
$200 |
Unlimited Premier 3 |
1 weekend - 2 weekday (Boat 15+ times) |
$6,450 |
$6,250 |
$200 |
Unlimited Premier 4 |
2 weekend - 2 weekday (Boat 30+ times) |
$8,950 |
$8,450 |
$500 |
Unlimited Weekday 2 |
2 weekday (Boat 15+ times) |
$4,950 |
$4,750 |
$200 |
What makes Carefree Different from other Boat Clubs?
Our membership plans:
Act quickly -- we currently have a limited number of memberships available in all Clubs - Bridgeport, Westport, Stamford, Rye and Old Saybrook.
Now let’s answer your questions. Throughout this email links are provided that send you to in-depth explanations of various topics that will help you better understand the Club and how Carefree Boat Club can be your way into affordable and trouble-free boating for you and your family!
- No onerous initiation fee, save thousands of dollars!
- Join one year at a time - no long term commitment required
- Spread your annual membership cost over 12 months
- Membership Plans designed to meet your family’s boating expectations and financial needs
- Over 180 clubs you can boat at nationally, boat all year long
- Newer and higher quality boats than other clubs
- 90% of our boats have bathroom facilities
- A variety of brands and models to choose from
- Boats range from 24 to 28 feet in length
- Single and twin engine boats
- Windlass anchoring
- Digital shifting
- All boats have GPS/fish finder units
- Quality stereo systems
- All new members will receive private On the Water training with our seasoned and certified captains.
- We offer advanced training opportunities through our Sea School to help you improve your nautical skills.
- Free dockside training to practice docking, navigation and more
Act quickly -- we currently have a limited number of memberships available in all Clubs - Bridgeport, Westport, Stamford, Rye and Old Saybrook.
Now let’s answer your questions. Throughout this email links are provided that send you to in-depth explanations of various topics that will help you better understand the Club and how Carefree Boat Club can be your way into affordable and trouble-free boating for you and your family!
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How much is membership?
We offer several membership plans to fit any lifestyle, providing your family with the opportunity to boat more than most New England boat owners boat at a fraction of the cost. Check out all of our plans above and pick the one that meets your budget and boating expectations! |
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Will I be able to make reservations on weekends?
If it is important that you boat most weekends you should consider the Annual Premier 4 membership. With the other membership levels it is more likely that you will be able to make reservations for every other weekend. CLICK HERE to see our fleet, learn more about how we provide the best availability in the business, and to see our reservation system in action! |
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How does it work?
At Carefree, we are proud to offer our members access to a variety of boats and locations so they can experience something new every time they boat! Your membership would entitle you to unlimited boating from our 5 location—Bridgeport, Westport, Stamford and Rye—as well as exclusive access to our boats in Old Saybrook. As a member, you could also reserve up to 3 outings each calendar year at every single Carefree Boat club throughout the US, Canada, the BVIs and Asia, with new clubs being added every year. CLICK HERE for more information on how you can boat around the world. |
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Training
Included in your membership is private training on how to safely operate our boats and navigate local waterways. With approximately 50% of our membership new to boating, we offer a comprehensive, real-world and hands-on training program that builds safe, capable and competent boaters. Along with this on the water training, members have unlimited access to dockside training with our staff. CLICK HERE for more about our members’ unlimited access to our locations and training. |
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