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.

2026 Berkshire Berkshire RFX CTS 2.75

Island Watersports

Second Wind

Length: 22 ft

Capacity: 11 people

Class: Boat

Location: Island Watersports

Exterior: Pearl White / Pearl White Interior: Lattee TT / Black Onyx 150 hp Mercury Motor, 2.75 Performance Package, Hydraulic Steering, Tilt Steering, Salt Water Package, Ski Tow Bar, 10' Power Electric Bimini Top, Wet Sounds MC-2 Head Unit and Sound System, Telescoping Swim Ladder For information on purchasing this boat, please contact the Island Watersports Sales Department at 302-537-2870.

Coming Soon

More details for Second Wind are coming soon!

2026 Berkshire Berkshire 24 UL LE 2.75

Island Watersports

Island Time

Length: 24 ft

Capacity: 12 people

Class: Boat

Location: Island Watersports

Exterior: Caribbean Blue / Caribbean Blue Interior: Granite/ Cobalt 2.75 Performance Package, Seastar Hydraulic Steering, Tilt Steering, Saltwater Edition, Ski Tow Bar, Power Electric Bimini, Lowrance Hook 5150 Chart Plotter, 150 hp Mercury motor, 10' Power Electric Bimini Top, Stainless Steel Telescoping Swim Ladder More information available at https://www.berkshirepontoon.com/berkshire-le/24UL%20LE%20B/1583 For information on purchasing this boat, please contact the Island Watersports Sales Department at 302-537-2870.

Coming Soon

More details for Island Time are coming soon!

2026 Alera Alera A22

Island Watersports

Shadow

Length: 22 ft

Capacity: 11 people

Class: Boat

Location: Island Watersports

200 hp Mercury outboard, Simrad NSX ULTRAWIDE chart plotter, Scanstrut Wireless Charger, Roswell Marine audio systems For information on purchasing this boat, please contact the Island Watersports Sales Department at 302-537-2870.

Coming Soon

More details for Shadow are coming soon!

2025 Berkshire Berkshire CL STS 3.0

Island Watersports

Risky Venture

Length: 23 ft

Capacity: 12 people

Class: Boat

Location: Island Watersports

200 Horsepower Mercury motor, Sport Tow Bar, Lowrance Elite Plus, Wireless Charger at the helm, Wet Sounds Audio with Bluetooth, Power Bimini Top For more information, please visit https://www.berkshirepontoon.com/berkshire-sts/23CL%20STS/1710 For information on purchasing this boat, please contact the Island Watersports Sales Department at 302-537-2870.

Coming Soon

More details for Risky Venture are coming soon!

2026 Berkshire Berkshire 24 RFC2 2.75

Island Watersports

Reel Escape (Designated Fishing Boat)

Length: 24 ft

Capacity: 11 people

Class: Boat

Location: Island Watersports

Exterior: Bronze / Pearl White 24RFC CTS 2.75 Performance Package, Hydraulic Steering, Tilt Steering, Saltwater Edition Package, Mercury 150 hp outboard motor Interior: Lattee TT/Caribou Brown 2 Midback chairs on stern with live well, Simrad 7" NSX3007, Wet Sounds MC-2 Head Unit and Sound System, Power Electric Bimini Top, Telescoping Swim Ladder This boat is not equipped to tow. For information on purchasing this boat, please contact the Island Watersports Sales Department at 302-537-2870.

Coming Soon

More details for Reel Escape (Designated Fishing Boat) are coming soon!

2026 Berkshire Berkshire RFX CTS 2.75

Island Watersports

Sea Spray

Length: 24 ft

Capacity: 13 people

Class: Boat

Location: Island Watersports

Exterior: Lagoon / Pearl White Interior: Smoke TT / Black Onyx Mercury 150 hp outboard motor, 2.75 Performance Package, aluminum underdeck, Salt Water Edition, Ski Tow Bar, Power Electric Bimini Top, Hydraulic Steering, Simrad 7" NSX3007, Wet Sounds MC-2 Head Unit and Sound System, Telescoping Swim Ladder For information on purchasing this boat, please contact the Island Watersports Sales Department at 302-537-2870.

Coming Soon

More details for Sea Spray are coming soon!

2026 Key West Key West 219FS

Island Watersports

Sea Dog (Designated Fishing Boat)

Length: 22 ft

Capacity: 5 people

Class: Boat

Location: Island Watersports

200 horsepower motor, Simrad, Clarion Fusion Audio, Centered Aerated Live Well in stern bench, Premium Independent Flip Bolster Leanpost, Console Seat w/ Cushion & Backrest, Full-Width Bench Seat w/ Removable Bottom Cushion, Stainless Steel Steering Wheel, Sea Star Hydraulic Tilt Steering, Self-Bailing Cockpit, , Molded-In Fiberglass Swim Platform w/ Ladder, Molded Anchor Locker w/Anchor, Compass, Bilge Pump w/ Auto Float Switch LED Livewell Lights, Bow Cushions, Bow Backrests, Bow Bolsters, Recessed Low Profile Bow Rail Deluxe Console: Windshield, Stainless Steel Grab Rail w/ Plenty Of Flush Mount Room, Electric Horn, Spacious Console w/ Light, Courtesy Lights, Power Outlet Plug On Dash, 4 Stainless-Steel Rod Holders w/ Drain Gunwale Rod Storage For 8' Rods, Molded Non-Skid Inner Liner, Folding Stern Light Cockpit Bolsters, Trim Tabs w/ Indicators, Console Footrest / Storage Box, Black Rubber Rub Rail, Built-In "Easy Access" Cooler Box Aft, Pull-Up Forward Cleat In Bow, Cup Holders Forward at bow seating. Hull Color: White For more information, please visit https://keywestboats.com/our-boats/219-fs For information on purchasing this boat, please contact the Island Watersports Sales Department at 302-537-2870.

Coming Soon

More details for Sea Dog (Designated Fishing Boat) are coming soon!

Offshore Account (Designated Fishing Boat)

2026 Key West Key West 239DFS

Island Watersports

Offshore Account (Designated Fishing Boat)

Length: 24 ft

Capacity: 9 people

Class: Boat

Location: Island Watersports

Equipped with a 250hp Mercury motor, hard top. Simrad, Deluxe Captains Chair And Back To Back Lounge Seat Bow Cushions, Wrap Around Aft Seating With Large Storage Box, SeaStar Hydraulic Tilt Steering, Self Bailing Cockpit, Aerated Live Well, Molded-In Fiberglass Swim Platform, Raw Water Wash Down System, Anchor Locker w/Anchor, Bilge Pump w/Auto Float Switch, Bluetooth Stereo, 4 Speakers & MP3 Port, Black Rubber Rub Rail, Curved Walk-Thru Windshield, Fish Box / Lockable Large Storage Box / Ski Locker In Floor, Rod Storage In Gunwale, Built-In "Easy Access" Cooler Box Aft, Dual Battery Switch, 8 Stainless Steel Cup Holders, Electric Horn, Courtesy Lights, Power Outlet Plug On Dash, Stainless-Steel Rod Holders w/ Drain, Gunwale Rod Storage, Foam Injected Fiberglass Stringer System, Molded Non-Skid Inner Liner, Built-In Fuel Tank, Folding Stern Light, Cockpit Bolsters, Closed Cell Positive Foam Floatation, 3 Rod Lockable Storage In Cabin, Granite Look Acrylic Counter Top With Sink, Low Profile Grab Rails In Bow, Acrylic Walk-Through Door With Latch, Convenient Storage Areas Throughout, 12" Trim Tabs w/ Indicators, Hull Color: White Note: Photo is a stock image. Options may vary. More Info at https://keywestboats.com/our-boats/239-dfs This boat will be slipped on the Harpoon Hanna's side of the marina. For information on purchasing this boat, please contact the Island Watersports Sales Department at 302-537-2870.

Coming Soon

More details for Offshore Account (Designated Fishing Boat) are coming soon!

2026 Scarab Scarab 235 Open

Island Watersports

Liquid Asset (Designated Fishing Boat)

Length: 23.5 ft

Capacity: 5 people

Class: Jet Boat

Location: Island Watersports

Liquid Blue hull, Twin 230 hp Rotax jet motors, T Top, two Aqua Amp Wireless Chargers at the helm, Simrad, Kicker Audio System, wireless phone charger. Two seat backs fold down at the stern to allow for larger stern platform. Tailgate also folds down. For more information, please visit https://www.scarabjetboats.com/us/trimgroup/235-open For information on purchasing this boat, please contact the Island Watersports Sales Department at 302-537-2870.

Coming Soon

More details for Liquid Asset (Designated Fishing Boat) are coming soon!

2025 Scarab Scarab 235 SE

Island Watersports

Blue Sky

Length: 23.5 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 has a bimini installed on it. Only Carefree staff should be taking this bimini top down, as the procedure requires multiple people and the attention to bimini arms not impacting windshield glass. Should you require that the bimini isn't installed, please notate on the reservation in advance for staff, to close and remove. For information on purchasing this boat, please contact the Island Watersports Sales Department at 302-537-2870.

Coming Soon

More details for Blue Sky are coming soon!

Carefree Fleet

2026 Berkshire Berkshire RFX CTS 2.75

Second Wind

Coming Soon

2026 Berkshire Berkshire 24 UL LE 2.75

Island Time

Coming Soon

2026 Alera Alera A22

Shadow

Coming Soon

2025 Berkshire Berkshire CL STS 3.0

Risky Venture

Coming Soon

2026 Berkshire Berkshire 24 RFC2 2.75

Reel Escape (Designated Fishing Boat)

Coming Soon

2026 Berkshire Berkshire RFX CTS 2.75

Sea Spray

Coming Soon

2026 Key West Key West 219FS

Sea Dog (Designated Fishing Boat)

Coming Soon

2026 Key West Key West 239DFS

Offshore Account (Designated Fishing Boat)

Coming Soon

2026 Scarab Scarab 235 Open

Liquid Asset (Designated Fishing Boat)

Coming Soon

2025 Scarab Scarab 235 SE

Blue Sky

Coming Soon

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