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The top boating charters in Summerland Key

Summerland Key

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Second Generation is a 2004 Yellowfin 36 Yellowfin Center console (restored in 2024), based out of Stock Island. 

Second Generation Key West/ Dry Tortugas park

Custom Cat Charters is a 2022 Honu Comfort Cat Catamaran based out of Marathon, offering an unforgettable experience for up to thirteen guests. 

Custom Cat Charters

Blind Squirrel Charters is a 2000 custom built sportfish based out of Stock Island. 

Blind Squirrel Charters

Don't miss your chance to experience a luxury charter in the Florida Keys, versatile enough for any on-water activity you can envision. 

Reel Paradise Charters

Step aboard our luxury 36’ Contender powered by triple 350s—perfect for sandbar hopping, snorkeling, or a high-speed run around Key West. 

36’ Contender – Triple 350s, Sandbar, Snorkel

Welcome aboard our private charter boat, accommodating up to 36 guests for an extraordinary backcountry sandbar experience tailored just for you! 

Salty Bottom Boats

Embark on an unforgettable adventure aboard the Ana Banana, a beautifully restored 2022 Luhrs Express Sport Fishing Yacht, now available for your ultimate cruising experience in Marathon. 

Ana Banana Fishing Company

Experience the ultimate adventure on the 2021 Axopar 37 XC, a sleek and versatile vessel based in Marathon. 

SeaEO I – Marathon

Ana Banana Fishing Company is a 2014 Grady White Release Center console (restored in 2023), based out of Marathon. 

Escape to the waters of Key West with Laid Back Key West, a sleek 2010 Intrepid 323 Center Console that guarantees an unforgettable day of fun and relaxation. 

Summerland Key: 71 boats available

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Summerland Key: 71 boats available

Second Generation Key West/ Dry Tortugas park

Custom Cat Charters

Blind Squirrel Charters

Reel Paradise Charters

36’ Contender – Triple 350s, Sandbar, Snorkel

Salty Bottom Boats

Ana Banana Fishing Company

SeaEO I – Marathon

Ana Banana Fishing Company

Laid Back Key West