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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$250-$500
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$250-$375
Sailboats
Set sail with these traditional wind-powered boats
$375-$500
Fishing Charters
Let a captain do the driving while you do the fishing
$300
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$375
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$300
Tamela
Private Islamorada Charters in the Florida Keys
Dawid "David" was great! Our family chose his charter services to celebrate our dad's 70th birthday, and our expectations were exceeded. We had a blast! He's very accommodating and chill. He is an EMT and paramedic, which added an extra level of peace of mind. His price is also very affordable for the services offered. Book with him; you won't be disappointed!
LF
Lisa
Boston Whaler 24ft Sandbar Hangout Key West
Anthony provides a great boating experience for anyone looking to explore around Key West. He had answers to every question my wife and I had and kept it fun for our teenage daughter and her friend. We explored some mangrove islands, snorkeled and paddle boarded. Anthony is a terrific guide and a lot of fun to talk with. Would recommend him to anyone looking to spend a few hours out on the water.
KH
Kelly
Boston Whaler 24ft Sandbar Hangout Key West
Anthony was awesome! Very personable easy going and down to earth. We wanted to go out experience the waters of the keys in the short time we had. Recommend 100%! Give him a try he's a patriot. Take care Anthony. Thanks for the finish to our vacation!!
JW
Jae
Boston Whaler 24ft Sandbar Hangout Key West
Captain Anthony is absolutely the best keys tour guide you could hope for. His boat is brand new and very comfortable. Everything was planned well and he was very accommodating in making the day exactly what we wanted it to be! Don’t hesitate at all... book a day with Captain Anthony!
Kelsey
Boston Whaler 24ft Sandbar Hangout Key West
Anthony was an awesome captain for our day trip! We met at a Marine with a fun little bar attached to it. Throughout the day he drove us around Key West and through the famous mangroves. We hungout at Snipes Sandbar and my husband and I drank lots off beer 😋 We saw dolphins sharks and a manatee! Anthony was very knowledgeable about boats and was great company for a fun day out on the water!
MH
Missy
Lets go boating like a local Sandbar hangout/ Island Hopping/ Paddle-boarding
Couldn’t have asked for a better 40th birthday! Anthony helped us decided on the best spots for what we wanted to do. Mystic the pug was a welcome bonus. The most amazing and unexpected part was the incredible drone footage of our party enjoying the water that Anthony shot and shared with us. Definitely book with Anthony!
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!