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.

2018 Crownline E21 XS

Hampton Bays

Crownline (BLK)-45G

Length: 21 ft

Capacity: 9 people

Class: Boat

Location: Hampton Bays

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)-45G are coming soon!

2021 Sailfish 220 CC

Hampton Bays

Sailfish center console-93G

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 Sailfish center console-93G are coming soon!

2021 Nautic Star Deck Boat

Sag Harbor

Nautic Star-Destination Sag Harbor Fee plus launch ride.-66g

Length: 23 ft

Capacity: 10 people

Class: Boat

Location: Sag Harbor

Destination usage for reciprocity of $500 due to high club costs for Sag Harbor plus Launch fee per person. 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-Destination Sag Harbor Fee plus launch ride.-66g 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!

2017 Crownline E1XS

East Moriches

Crownline (Blue)-45G

Length: 21.5 ft

Capacity: 9 people

Class: Boat

Location: East Moriches

No additional description available.

Coming Soon

More details for Crownline (Blue)-45G are coming soon!

2013 Southwind Southwind Deck Boat

East Moriches

Southwind-55g

Length: 24 ft

Capacity: 8 people

Class: Boat

Location: East Moriches

No additional description available.

Coming Soon

More details for Southwind-55g are coming soon!

2023 Pioneer 202 Sport Fish

East Moriches

Pioneer (Grey)-59G

Length: 20 ft

Capacity: 8 people

Class: Boat

Location: East Moriches

No additional description available.

Coming Soon

More details for Pioneer (Grey)-59G are coming soon!

2022 Pioneer 202 Islander

East Moriches

Pioneer (White)-59G

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)-59G are coming soon!

2025 Boston Whaler Montauk

East Moriches

Boston Whaler Beach Boat-35g

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-35g are coming soon!

2016 Key West Dual Console

East Moriches

Key West Dual Console-50G

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-50G are coming soon!

2010 Nautic Star Nautic Star

East Moriches

Nautic Star Flat Boat-35G

Length: 18 ft

Capacity: 6 people

Class: Boat

Location: East Moriches

No additional description available.

Coming Soon

More details for Nautic Star Flat Boat-35G are coming soon!

2027 SunCatcher Picnic Boat

East Moriches

Blue/White Day Lily Beach Boat

Length: 17 ft

Capacity: 4 people

Class: Navigator

Location: East Moriches

Silly Lily Beach Club members!!!! Take one of our Amalfi Coast inspired Day Lily beach boats out to a sandy isle or to the beach. Great for Picnics and touring around and sunset anchoring.

Coming Soon

More details for Blue/White Day Lily Beach Boat are coming soon!

2027 SunChaser Pink Striped Day Lily

East Moriches

Pink Striped Day Lily Beach Boat

Length: 17 ft

Capacity: 4 people

Class: Navigator

Location: East Moriches

Silly Lily Beach Club members!!!! Take one of our Amalfi Coast inspired Day Lily beach boats out to a sandy isle or to the beach. Great for Picnics and touring around and sunset anchoring.

Coming Soon

More details for Pink Striped Day Lily Beach Boat are coming soon!

2027 SunChaser Yellow Striped Day Lily

East Moriches

Yellow Day Lily Beach Boat

Length: 17 ft

Capacity: 4 people

Class: Navigator

Location: East Moriches

No additional description available.

Coming Soon

More details for Yellow Day Lily Beach Boat are coming soon!

2027 Angler Bristol Skiff - 40HP

East Moriches

Power Skiff

Length: 18 ft

Capacity: 4 people

Class: Navigator

Location: East Moriches

Take out our our Bristol Skiff and get in where other anglers cant. With a 40Hp Motor, your sure to get where you want to be quickly. Or take it to the beach, clamming or on an excursion. COmes with a Bimini top as well.

Coming Soon

More details for Power Skiff are coming soon!

2027 Sundance Skiffs 17 FT SKIFF

East Moriches

CENTER CONSOLE STURDY DORY

Length: 17 ft

Capacity: 4 people

Class: Navigator

Location: East Moriches

Go Fishing or just get out on the bay with our beautifully restored Sturdy Dory center console with a 25 HP engine. This boat can be used for clamming, fishing or for a day on the bay.

Coming Soon

More details for CENTER CONSOLE STURDY DORY are coming soon!

Carefree Fleet

2018 Crownline E21 XS

Crownline (BLK)-45G

Coming Soon

2021 Sailfish 220 CC

Sailfish center console-93G

Coming Soon

2021 Nautic Star Deck Boat

Nautic Star-Destination Sag Harbor Fee plus launch ride.-66g

Coming Soon

2026 Axopar Boats 750

Lekker 750

Coming Soon

2017 Crownline E1XS

Crownline (Blue)-45G

Coming Soon

2013 Southwind Southwind Deck Boat

Southwind-55g

Coming Soon

2023 Pioneer 202 Sport Fish

Pioneer (Grey)-59G

Coming Soon

2022 Pioneer 202 Islander

Pioneer (White)-59G

Coming Soon

2025 Boston Whaler Montauk

Boston Whaler Beach Boat-35g

Coming Soon

2016 Key West Dual Console

Key West Dual Console-50G

Coming Soon

2010 Nautic Star Nautic Star

Nautic Star Flat Boat-35G

Coming Soon

2027 SunCatcher Picnic Boat

Blue/White Day Lily Beach Boat

Coming Soon

2027 SunChaser Pink Striped Day Lily

Pink Striped Day Lily Beach Boat

Coming Soon

2027 SunChaser Yellow Striped Day Lily

Yellow Day Lily Beach Boat

Coming Soon

2027 Angler Bristol Skiff - 40HP

Power Skiff

Coming Soon

2027 Sundance Skiffs 17 FT SKIFF

CENTER CONSOLE STURDY DORY

Coming Soon

Manufacturer Brands

Quick Links

Subscribe to our Email List