Island Hopping in Florida Keys
65 boats available
The best out of 65 deals in Florida Keys - enter dates to check availability
Top Island Hopping in Florida Keys Destinations
Top Island Hopping in Florida Keys
Florida Keys: 65 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. "Highest recommendation for Capt Jen! She was a great guide for a wonderful morning on the water for my wife and two daughters." — Zach, 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. "We booked our charter and as the day got closer we saw that it was supposed to be super windy." — Heather, 2 Hour Private Charter AFTERNOON
Instant confirmation
2 adults • 0 children
US $349
US $349
Nice Guy Charters
Stock Island • 24 ft • 6 persons
6 Hour – Boat Tour & Sand - 9 AM
6 hour trip • starts at 09:00 AM
Nice Guy Charters is a 2004 Everglades 243cc Center console (restored in 2024), based out of Stock Island. "Captain Jeff was quick to respond to our booking and asked us what our priorities would be for the trip." — Corey, 6 Hour – Boat Tour & Sand - 9 AM
Instant confirmation
2 adults • 0 children
US $750
US $750
Bamboo Charters
Islamorada • 25 ft • 6 persons
2 Hour - Private Charter Afternoon
2 hour trip • starts at 01:30 PM
Step aboard the 2022 Parker 25 SE Center Console, your gateway to the turquoise waters of the Florida Keys. "Matt was a great captain, allowed us to go to a quieter spot for snorkeling as it was a busy holiday weekend." — Christina, 2 Hour - Private Charter Afternoon
Instant confirmation
2 adults • 0 children
US $350
US $350
Capt. Lew Luxury 32’ Worldcat multi activity
Key Largo • 32 ft • 6 persons
4 Hour Cruise 10AM start
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 Cruise 10AM start
Instant confirmation
2 adults • 0 children
US $890
US $890
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. "Larry was great and took us anywhere we really wanted to go." — Jamie, 4 Hour – Boating Adventure (AM)
Instant confirmation
2 adults • 0 children
US $550
US $550
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
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 $500
US $500
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
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!
"Captain Charlie is amazing! He asked us what type of experience we were looking for then took us to some beautiful spots." — David, Bar Hopping
Instant confirmation
2 adults • 0 children
US $590
US $590
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 did the 4 hour option from Marathon with Captain Daniel and had the most incredible time." — Elizabeth,
Instant confirmation
trips fromUS $899
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