Island Hopping in Florida Keys
73 boats available
The best out of 73 deals in Florida Keys - enter dates to check availability
Top Island Hopping in Florida Keys Destinations
Top Island Hopping in Florida Keys
Florida Keys: 73 boats available
Kilo Whiskey Charters - Sunset and Snorkeling
5.0
/5
(4 reviews)
•
58 external reviews
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. "We did a 4 hour trip with Captain Anthony. What an amazing experience." — Michael, 4 Hour Trip – Sandbar Eco Tour
Instant confirmation
2 adults • 0 children
US $600
US $600
Bamboo Charters
5.0
/5
(31 reviews)
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. "Captain Matt was great! He has an Impressive knowledge of the ecological makeup of the keys." — Dominic, 2 Hour - Private Charter Afternoon
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2 adults • 0 children
US $350
US $350
Livin’ the Dream Charters LLC
5.0
/5
(8 reviews)
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
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2 adults • 0 children
US $500
US $500
Living Like Larry Charters
4.9
/5
(23 reviews)
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. "My mom, sister and I booked Larry for a four hour trip and we all wished we had done eight!" — Allison, 4 Hour – Boating Adventure (AM)
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2 adults • 0 children
US $550
US $550
Islamorada Private Charters
5.0
/5
(25 reviews)
Islamorada • 26 ft • 6 persons
2 Hour Private Charter AFTERNOON
2 hour trip • starts at 01:30 PM
Islamorada Private Charters - Luxury Catamaran Experience
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
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2 adults • 0 children
US $395
US $395
Capt. Lew Luxury 32’ WorldCat multi activity
5.0
/5
(32 reviews)
Key Largo • 32 ft • 6 persons
4 Hour Cruise 10AM start
4 hour trip • starts at 10:00 AM
Enjoy a private personalized adventure with Captain Lew on our 32 foot WorldCat catamaran in Key Largo.
"We hired Capitan Lew for a day in the water and he did not disappoint." — Jim, 4 Hour Cruise 10AM start
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2 adults • 0 children
US $890
US $890
Keys Aquatic Adventures
4.8
/5
(11 reviews)
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
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2 adults • 0 children
US $590
US $590
Island Ryder Charters
5.0
/5
(33 reviews)
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. "We booked Captain Jen for a snorkeling trip while staying in Marathon and it was awesome!" — Vanessa, 2 Hour Eco Tour
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2 adults • 0 children
US $300
US $300
Nautical Tiki Islamorada
5.0
/5
(12 reviews)
Islamorada • 23 ft • 6 persons
3 hour Private Charter & Sandbar PM
3 hour trip • starts at 01:00 PM
Experience the ultimate island escape aboard the Nautical Tiki Islamorada, a stunning 2023 Beach Cat Tiki Catamaran, perfect for unforgettable adventures in the heart of Islamorada. "We had such a lovely time with Captain Merv. He’s just a good guy to talk with, and he was very knowledgeable." — Ricky, 3 hour Private Charter & Sandbar PM
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2 adults • 0 children
US $495
US $495
Southern Tauk Charters
5.0
/5
(16 external reviews)
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,
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trips fromUS $450
Tiki Boat Adventures - Key West
5.0
/5
(6 reviews)
Key West • 20 ft • 6 persons
Ditch the ordinary and immerse yourself in a tropical escape with Tiki Boat Adventures in Key West! "Amazing day on the water. Madison was a great captain. Before we started she had everything we brought on board in place ready to go." — DIANNE,
Instant confirmation
trips fromUS $375
Ana Banana Fishing Company
5.0
/5
(1 review)
•
5+ external reviews
Marathon • 40 ft • 6 persons
4 Hr – Ultimate Boating Adventure
4 hour trip • starts at 08:00 AM
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. 4 Hr – Ultimate Boating Adventure
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2 adults • 0 children
US $995
US $995
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