Island Hopping in Florida Keys
58 boats available
The best out of 58 deals in Florida Keys - enter dates to check availability
Top Island Hopping in Florida Keys Destinations
Top Island Hopping in Florida Keys
Florida Keys: 58 boats available
Island Ryder Charters
Islamorada • 23 ft • 6 persons
2 Hour Eco Tour
2 hour trip • starts at 09:00 AM
Experience Islamorada Like Never Before!
There is no better way to immerse yourself in the natural beauty and vibrant marine life of Islamorada than by setting sail on a private charter. "Don’t think about it, just book it! Jen was fantastic, she’s knowledgeable, personable, easy going and makes sure the day is filled with something for everyone." — Tracy, 2 Hour Eco Tour
Instant confirmation
2 adults • 0 children
US $300
US $300
Kilo Whiskey Charters - Sunset and Snorkeling
Key West • 33 ft • 6 persons
4 Hour Trip – Sandbar Eco Tour
4 hour trip • starts at 10:00 AM
Welcome to Kilo Whiskey Charters, the premier destination for unforgettable aquatic adventures in the pristine waters of Key West, Florida. "Captain Anthony was very knowledgeable and we had a great day on a custom adventure out to Dry Tortugas and the lighthouse." — Heather, 4 Hour Trip – Sandbar Eco Tour
Instant confirmation
2 adults • 0 children
US $600
US $600
Islamorada Private Charters
Islamorada • 26 ft • 6 persons
2 Hour Private Charter AFTERNOON
2 hour trip • starts at 02:00 PM
Islamorada Private Charters - Luxury Catamaran Experience (2019 Custom Build)
Set sail aboard the stunning Islamorada Private Charters, a custom-built 2019 catamaran offering an unforgettable adventure in the heart of the Florida Keys. " Captain Don greeted us with a Manatee was in distress in the harbor and ask if we would
Like to help locate it." — Curt, 2 Hour Private Charter AFTERNOON
Instant confirmation
2 adults • 0 children
US $349
US $349
Capt. Lew Luxury 32’ Worldcat multi activity
Key Largo • 32 ft • 6 persons
4 Hour Trip morning
4 hour trip • starts at 10:00 AM
Captain Lew Charter offers a private luxury experience on our 2023 World Cat 325DC Catamaran in Key Largo. "My family and I had a wonderful time with Captain Lew. He and his wife Sheri(sorry if I misspelled) are such sweet people and provide a wonderful private boating experience." — Erin, 4 Hour Trip morning
Instant confirmation
2 adults • 0 children
US $890
US $890
Livin’ the Dream Charters LLC
Little Torch Key • 25 ft • 6 persons
4 hr- Bar/Restaurant Happy Hour Hop
4 hour trip • starts at 11:00 AM
Climb aboard Livin’ the Dream Charters LLC, a beautifully restored 1987 Downeaster Tunnel Hull Center Console, based out of scenic Little Torch Key. "This was a short visit to the keys for our family and we booked a sunset cruise so the kids could get out on the water to see a a beautiful sunset." — Shawn, 4 hr- Bar/Restaurant Happy Hour Hop
Instant confirmation
2 adults • 0 children
US $400
US $400
SeaEO I – Marathon
Marathon • 38 ft • 13 persons
Experience the ultimate adventure on the 2021 Axopar 37 XC, a sleek and versatile vessel based in Marathon. "We had a great trip on our boat ride with Captian Daniel. JP was great to work with when scheduling and booking the trip." — Donna,
Instant confirmation
trips fromUS $799
Keys Aquatic Adventures
Islamorada • 25 ft • 6 persons
Bar Hopping
4 hour trip • starts at 08:00 AM
Uncover the Magic of Islamorada with Keys Aquatic Adventures!
"Charlie was great! Friendly, laid back, and wants to make sure you have a good time." — Aimee, Bar Hopping
Instant confirmation
2 adults • 0 children
US $590
US $590
Bamboo Charters
Islamorada • 25 ft • 6 persons
Step aboard the 2022 Parker 25 SE Center Console, your gateway to the turquoise waters of the Florida Keys. "Went online to book an Islamorada sandbar trip. After reviewing all the choices decided on Bamboo Charters." — Frank,
Instant confirmation
trips fromUS $250
Double Decker Tritoon with Waterslide
Marathon • 26 ft • 6 persons
Double Decker Tritoon with Waterslide is a 2021 Grand Island Double Decker Waterslide Pontoon based out of Marathon. "I came down to Marathon with my husband and 2 kids last weekend (Feb 2025), and wanted a no-stress excursion for the whole family." — BoatBooker Member,
Instant confirmation
trips fromUS $549
Southern Tauk Charters
Tavernier • 23 ft • 6 persons
Southern Tauk Charters is a 2023 Sea Hunt Center console based out of Tavernier. "“What an incredible day on the water with Captain Mike! It was clear from the start that Mike knew all the lively and serene spots to hang out, have fun, and relax ." — BoatBooker Member,
Instant confirmation
trips fromUS $450
Island Adventures
Islamorada • 19 ft • 6 persons
4 Hour – Adventure, Your Way! (AM)
4 hour trip • starts at 09:00 AM
Embark on the ultimate island getaway aboard Island Adventures, a beautifully restored 2006 Godfrey Hurricane Sun Deck Deck Boat (refurbished in 2024). "We had a great day on the water with Captain Jim. Started off snorkeling in a protected cove which was great for my eight year old." — Bohdan, 4 Hour – Adventure, Your Way! (AM)
Instant confirmation
2 adults • 0 children
US $649
US $649
Living Like Larry Charters
Marathon • 24 ft • 6 persons
4 Hour – Boating Adventure (AM)
4 hour trip • starts at 09:00 AM
Set sail aboard the stunning 2016 NauticStar 243DC Deck Boat, docked in the picturesque Marathon. "There were 6 of us. He was so accommodating. We just wanted a laid back cruise and he showed us some really cool spots and stopped at a sandbar." — Lisa, 4 Hour – Boating Adventure (AM)
Instant confirmation
2 adults • 0 children
US $550
US $550
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