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
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 01:30 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 $395
US $395
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. "“Captain Larry gave us an unforgettable experience! He was incredibly friendly, courteous, and accommodating from start to finish." — Guy, 4 Hour – Boating Adventure (AM)
Instant confirmation
2 adults • 0 children
US $550
US $550
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. "Matthew was very accommodating in adjusting our schedule for a possible storm coming." — William, 2 Hour - Private Charter Afternoon
Instant confirmation
2 adults • 0 children
US $350
US $350
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
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
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!
"We had amazing experience and day on the water. Definitely will booking with them next trip here." — Jaclyn, Bar Hopping
Instant confirmation
2 adults • 0 children
US $590
US $590
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. "Jen was a great boat captain. The wind was a little high, but, Jen had alternative locations for our family to snorkel and hang out at a sandbar." — Luke, 2 Hour Eco Tour
Instant confirmation
2 adults • 0 children
US $300
US $300
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
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
Ana Banana Fishing Company
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
Instant confirmation
2 adults • 0 children
US $995
US $995
Sandbar/Snorkel/ Dolphins/Sunset Trips
Key West • 27 ft • 6 persons
Step aboard a beautifully restored 1985 SeaVee Ocean Center Console, meticulously updated in 2010, and get ready for an unforgettable adventure. "Captain Tony made our charter A++. He was great about communicating with us in advance to ensure our day was perfect." — Heather,
Instant confirmation
trips fromUS $350
View all boat rentals
See all 65 boat rentals in Florida Keys