Carefree Boat Sales

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.

Spotlight Boat

2025 Seafox 228 Commander

HP | 150
Seats | 8
Includes | Depth finder, bluetooth radio
Located at | Hampton’s Landing

BRAND NEW

2024 Berkshire Berkshire 22 RFX CTS 2.75

Island Watersports

Black & Tan

Length: 22 ft

Capacity: 11 people

Class: Boat

Location: Island Watersports

Equipped with a Mercury 150 hp motor, Ski Tow Bar, Lowrance Hook 5 Navigation Display, 25" Tubes Center with Sport Tube, Seastar Hydraulic Steering with Power Assist Steering Pump and Tilt Steering, Electric Bimini Top, "Black Out" Trim Package with black anodized rails, black anodized bimini top frame, black rail spacers, black pinch guards, black door stops, black rail plugs, black snap screws, black pedestals

Coming Soon

More details for Black & Tan are coming soon!

2025 Berkshire Berkshire 22 CL CTS

Island Watersports

Calypso (Fishing License)

Length: 22 ft

Capacity: 11 people

Class: Boat

Location: Island Watersports

Equipped with a Mercury 150 hp motor, Lowrance Hook 5 Navigation Display, Power Electric Bimini, 25" Tubes Center with Sport Tube, Aluminum Underdeck, Seastar Hydraulic Steering, and Tilt Steering. This boat has a Maryland fishing license, but does not have any specific equipment for fishing.

Coming Soon

More details for Calypso (Fishing License) are coming soon!

2024 Berkshire Berkshire 23 RFC2 STS 2.75

Island Watersports

Fish On (Designated Bay Fishing Boat)

Length: 23 ft

Capacity: 12 people

Class: Boat

Location: Island Watersports

2.75 Performance Package with Seastar Hydraulic Steering, Power Electric Bimini Top, Mercury 150hp, Ski Tow Sports Bar, Lowrance Elite FS 7, Saltwater Edition, Live Well, Centric II Stern Fishing Chairs. This boat has a Maryland fishing license. Exterior: Platinum / Black Onyx Panel Interior: Furniture Base: Latte TT, Accent Black Onyx

Coming Soon

More details for Fish On (Designated Bay Fishing Boat) are coming soon!

2025 Berkshire Berkshire RFX STS

Island Watersports

Pegasus

Length: 23 ft

Capacity: 12 people

Class: Boat

Location: Island Watersports

Power electric Bimini, 150 horsepower Mercury outboard, Lowrance Elite FS, WetSounds audio system with Bluetooth, RGB lighting, wireless charger at helm

Coming Soon

More details for Pegasus are coming soon!

2025 Berkshire Berkshire CL STS

Island Watersports

Shell Game

Length: 23 ft

Capacity: 12 people

Class: Boat

Location: Island Watersports

This boat is equipped with a 200 horsepower Mercury outboard, power bimini, Lowrance Elite Chart Plotter, wireless phone charger, Wet Sounds audio system with bluetooth, and RGB under seat and speaker back lighting. This boat requires an all day reservation.

Coming Soon

More details for Shell Game are coming soon!

2025 Berkshire Berkshire 24 RFC CTS

Island Watersports

Deep Blue (Designated Bay Fishing Boat)

Length: 24 ft

Capacity: 13 people

Class: Boat

Location: Island Watersports

Equipped with live well, 2 midback chairs, 150 horsepower Mercury motor, Power Electric Bimini, Lowrance Hook 5 Display, 2.75 Performance Package including 25" tubes, center sport tube, aluminum underdeck, large lifting strakes on inside of the outer tubes, Seastar Hydraulic Steering, and Tilt Steering.

Coming Soon

More details for Deep Blue (Designated Bay Fishing Boat) are coming soon!

2024 Four Winns Four Winns HD5C OB (Not Equipped for Watersports)

Island Watersports

Why Knot

Length: 25 ft

Capacity: 13 people

Class: Boat

Location: Island Watersports

White Exterior with Black stripe, with Lunar Cockpit color, GPS Plotter, 250 Horsepower Mercury outboard, bow and aft swim platforms and ladders, usb charge port, stereo with AM/FM/Bluetooth, in floor ski locker. For inquiries regarding purchasing this boat, please contact Josh Klein at Island Watersports 302-537-2628 [email protected].

Coming Soon

More details for Why Knot are coming soon!

2025 Scarab Scarab 235 SE

Island Watersports

Blue Sky

Length: 23 ft

Capacity: 10 people

Class: Jet Boat

Location: Island Watersports

Denium Blue/White Hull, Twin Rotax 230 Motors, Bow and Stern Swim Platforms, Ski Tow, convertible aft seating, Scarab custom gauges and instrumentation fuel level, tach, gps speed, hour meter, compass, depth sounder, cruise control, 12 v outlet, in-floor ski locker, JL Audio Stereo System with Bluetooth, Speakers, wakeboard tower. THIS BOAT CURRENTLY DOES NOT HAVE A STERN SWIM LADDER.

Coming Soon

More details for Blue Sky are coming soon!

Fishy Business (Designated Bay Fishing Boat)

2024 Scarab Scarab 255 Open

Island Watersports

Fishy Business (Designated Bay Fishing Boat)

Length: 25 ft

Capacity: 13 people

Class: Jet Boat

Location: Island Watersports

Seafoam Green / White, Interior Neutral with Black Accent, Twin Rotax 170 horsepower motors, GPS Plotter with Depth Sounder, Bow and Stern Swim Platforms, Tailgate, T-Top with tow point, self bailing cockpit, enclosed changing room, Bluetooth Stereo For inquiries regarding purchasing this boat, please contact Josh Klein at Island Watersports 302-537-2628 [email protected].

Coming Soon

More details for Fishy Business (Designated Bay Fishing Boat) are coming soon!

Cast Away (Designated Off-Shore or Bay Fishing Boat)

2024 Sea Born Sea Born LX 24

Island Watersports

Cast Away (Designated Off-Shore or Bay Fishing Boat)

Length: 24 ft

Capacity: 10 people

Class: Twin Engine

Location: Island Watersports

White Exterior, Twin Engine 150 horsepower Mercury outboards, live well, rocket launcher, rod storage in the gunnels. This boat is not equipped with a table. For inquiries regarding purchasing this boat, please contact Josh Klein at Island Watersports 302-537-2628 [email protected].

Coming Soon

More details for Cast Away (Designated Off-Shore or Bay Fishing Boat) are coming soon!

Carefree Boat Sales

Spotlight Boat

Spotlight Boat

BRAND NEW

2024 Berkshire Berkshire 22 RFX CTS 2.75

Black & Tan

Coming Soon

2025 Berkshire Berkshire 22 CL CTS

Calypso (Fishing License)

Coming Soon

2024 Berkshire Berkshire 23 RFC2 STS 2.75

Fish On (Designated Bay Fishing Boat)

Coming Soon

2025 Berkshire Berkshire RFX STS

Pegasus

Coming Soon

2025 Berkshire Berkshire CL STS

Shell Game

Coming Soon

2025 Berkshire Berkshire 24 RFC CTS

Deep Blue (Designated Bay Fishing Boat)

Coming Soon

2024 Four Winns Four Winns HD5C OB (Not Equipped for Watersports)

Why Knot

Coming Soon

2025 Scarab Scarab 235 SE

Blue Sky

Coming Soon

2024 Scarab Scarab 255 Open

Fishy Business (Designated Bay Fishing Boat)

Coming Soon

2024 Sea Born Sea Born LX 24

Cast Away (Designated Off-Shore or Bay Fishing Boat)

Coming Soon

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