Carefree Fleet

Carefree Boat Club has a great mix of boats for everyone, so your day on the water is always a blast. Whether you're looking to fish or need a roomy boat for the whole family, we’ve got you covered. With so many options to choose from, your membership makes sure every outing is a great one! Our fleet is continually updated check out a sampling of some of our best boats across the country.

2021 Sailfish 220 CC

Hampton Bays

Just Foolin' Around

Length: 21 ft

Capacity: 8 people

Class: Boat

Location: Hampton Bays

Spend the day fishing on our well-equipped Sailfish 220. Center console spaciousness meets family-friendly versatility with an array of features and options for fishing trips and fun-filled outiings. Features include: built-in GPS system, surround sound Bluetooth stereo, live well, cooler, courtesy lighting, comfortable seating with backrests (forward and aft), rinse-off station and T-top for shade.

Coming Soon

More details for Just Foolin' Around are coming soon!

2023 Pioneer 202 Sport Fish

Hampton Bays

Pioneer (Grey)

Length: 20 ft

Capacity: 8 people

Class: Boat

Location: Hampton Bays

No additional description available.

Coming Soon

More details for Pioneer (Grey) are coming soon!

2013 Southwind Southwind Deck Boat

Safe Harbor Greenport

Southwind

Length: 24 ft

Capacity: 8 people

Class: Boat

Location: Safe Harbor Greenport

No additional description available.

Coming Soon

More details for Southwind are coming soon!

2021 Nautic Star Deck Boat

Sag Harbor

Nautic Star

Length: 23 ft

Capacity: 10 people

Class: Boat

Location: Sag Harbor

The Nauticstar with its rugged Deep-Vee hull and U-shaped wraparound cockpit ensure a comfortable ride for everyone. A panoramic walk-through windshield, enclosed dressing room, leather touch upholstery and stereo system are just a few of its creature comforts. A Seadek transom landing and forward and aft boarding ladders extend the fun beyond the boat. Take it up a notch. If you want to go fishing book one of our fishing boats please. We have fishing packages available.

Coming Soon

More details for Nautic Star are coming soon!

2026 Axopar Boats 750

Sag Harbor

Lekker 750

Length: 25 ft

Capacity: 10 people

Class: Boat

Location: Sag Harbor

Built in Amsterdam of high grade aluminum this boat is designed for adventure and the social life. Crafted from raw aluminium and designed around an open, social layout. A real head turner of a boat.

Coming Soon

More details for Lekker 750 are coming soon!

2022 Pioneer 202 Islander

East Moriches

Pioneer (White)

Length: 20 ft

Capacity: 8 people

Class: Boat

Location: East Moriches

We like to call this our hybrid boat because the Pioneer is great for family beach trips or an afternoon of fishing. Features include: comfortable plush seating with a full transom bench seat, wrap-around bolsters throughout, surround sound Bluetooth stereo, built-in GPS, cooler, dual swim platform, courtesy and down lights, rinse-off station and T-top for shade.

Coming Soon

More details for Pioneer (White) are coming soon!

2018 Crownline E21 XS

East Moriches

Crownline (BLK)

Length: 21 ft

Capacity: 9 people

Class: Boat

Location: East Moriches

Luxury meets family boating fun on the Crownline 21.5 XLS. Complete with a spacious sun lounge, ample wrap-around seating and a dinette table for serving, this boat has everything you need for entertaining family and friends on the water. Features include: marine carpeting throughout, surround sound Bluetooth stereo, built-in GPS, cooler, integrated swim platform, courtesy lighting, rinse-off station, sun bimini top.

Coming Soon

More details for Crownline (BLK) are coming soon!

2017 Crownline E1XS

East Moriches

Crownline (Blue)

Length: 21.5 ft

Capacity: 9 people

Class: Boat

Location: East Moriches

No additional description available.

Coming Soon

More details for Crownline (Blue) are coming soon!

2025 Boston Whaler Montauk

East Moriches

Boston Whaler Beach Boat

Length: 17 ft

Capacity: 5 people

Class: Boat

Location: East Moriches

The perfect Beach Boat. COmes with Beach Chairs, Umbrella and Cooler. The Boston Whaler Montauk is nimble, easy to captain and tons of fun. This nimble center console model retains its clean, timeless aesthetic and rugged utility while providing enhanced comfort, performance and versatility. Count on all the features you need to get the job done, and the impeccable quality you know to expect from Boston Whaler - and fall in love all over again with the 170 Montauk.

Coming Soon

More details for Boston Whaler Beach Boat are coming soon!

2016 Key West Dual Console

East Moriches

Key West Dual COnsole

Length: 20 ft

Capacity: 7 people

Class: Boat

Location: East Moriches

Dual Console with tow bar and Head. Garmin GPS. Perfect boat for family fun and adventures.

Coming Soon

More details for Key West Dual COnsole are coming soon!

2010 Nautic Star Nautic Star

East Moriches

Nautic Star Flat Boat

Length: 18 ft

Capacity: 6 people

Class: Boat

Location: East Moriches

No additional description available.

Coming Soon

More details for Nautic Star Flat Boat are coming soon!

Carefree Fleet

2021 Sailfish 220 CC

Just Foolin' Around

Coming Soon

2023 Pioneer 202 Sport Fish

Pioneer (Grey)

Coming Soon

2013 Southwind Southwind Deck Boat

Southwind

Coming Soon

2021 Nautic Star Deck Boat

Nautic Star

Coming Soon

2026 Axopar Boats 750

Lekker 750

Coming Soon

2022 Pioneer 202 Islander

Pioneer (White)

Coming Soon

2018 Crownline E21 XS

Crownline (BLK)

Coming Soon

2017 Crownline E1XS

Crownline (Blue)

Coming Soon

2025 Boston Whaler Montauk

Boston Whaler Beach Boat

Coming Soon

2016 Key West Dual Console

Key West Dual COnsole

Coming Soon

2010 Nautic Star Nautic Star

Nautic Star Flat Boat

Coming Soon

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