Key West, FL > Boat Tours
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11/29/2020 ~ 12/04/2020
November 2020

Key West Boat Tours

Key West Sunset Dinner Cruise

Key West Sunset Dinner Cruise

137 ratings
Duration2 Hrs.
Enjoy a delicious dinner, drinks, and a beautiful sunset at sea with a friendly crew. Dig in to an incredible tropical...
The cuze was awesome bartender and live DJ was at point with everyone. Highly recommended to everyone.
It was a great experience. Would recommend if you want to see a sunset and have some rum drinks. Food was very good and good value for the price. Music was entertaining. Not good for children. If you got a sitter go do it!
We thoroughly enjoyed our sunset dinner cruise with the crew is sunsetsports! They kept us with a drink in our hand the entire time and the dinner was wonderful. The sunset was SPECTACULAR!!!!!
from $69
Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

11 ratings
Duration3 Hrs.
Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Dolphin Watch Sunset...
So enjoyable, relaxing & fun! Great value! Happy with the food, wine & staff. Can’t wait to go again!
My crew was knowledgeable, watched out for us, food was good. We saw a lot of dolphins and crew gave us a chat about these non-migratory ones that live in waters near Key West. The best thing about the cruise is that we were a small group of about 15 persons. Great! You should add Coke Zero to the drinks.
My husband and I booked this cruise through Tripshock for our 5th anniversary and it was amazing! The dolphins were in abundance! The crew was personable and the drinks and appetizers were good as well. We highly recommend!
from $80
Wind and Wine Sunset Sail

Wind and Wine Sunset Sail

30 ratings
Duration2 Hrs.
Sail into the Key West sunset while sampling 8 fine wines from around the world, beer, and delicious hors d'oeuvres....
The crew was wonderful! Meg & other stew were great! Tony was a good skipper
A fun crew, beautiful ship, Wine and cheese were yummy, breathtaking sunset! Only thing that could have made it a better evening would have been seats or stadium pads :0) it’s a sail boat so your sitting on the deck...which after and hour or so is a bit uncomfortable.
This was a first-class outing from the captain and crew to the wine and food to the beautiful Key West Sunset. We even had an on-board wedding to make us all feel a little more romantic. If you're visiting the Keys, don't miss this trip!
Day Sail Aboard Schooner America 2.0

Day Sail Aboard Schooner America 2.0

5 ratings
Duration1.5 Hrs.
Explore the high seas in style on the Schooner America 2.0, namesake of the first sailboat to win the America's Cup in...
We had a fabulous sail with our all female crew of Amber Heather and Mary! Very fun and knowledgeable as well as excellent sailors! The boat was gorgeous! The allotted time went way too fast...We will certainly go out again on next trip to the Keys!
Wonderful experience sailing with this all female crew under the guidance of Captain Amber...cheerful, knowledgeable and welcoming ... they taught us safety and all about the coral reef!
Highly recommend! The crew was professional and just a lot of fun. The boat is spotlessly clean. I have never sailed. This was a great introduction. I enjoyed every minute. I wish I could remember the names of the crew who worked with Captain Ron. They deserve a shout out!!! Smart women, passionate about their work. And did I say fun????
Rum Runner Bar Boat Castaway Cruise
Enjoy this Rum Runner Bar Boat Castaway Cruise and get out on the water for some fun to last the summer through. Cruise...
Island Hopper Speedboat Excursion for Two
This is the best kept secret in Key West! Hop in your own personal mini speedboat and follow your knowledgeable guide...
Seabreeze Dolphin & Snorkel Tour
Be on the lookout for Key West’s magnificent dolphins while cruising the crystal clear backcountry waters of the Gulf...
Private 4 Hour Key West Fishing Charter (for 6 Guests)
All Aboard this center console for a day of fun in the sun, fishing your hearts out with this Private Half Day Key West...
Cycleboat Cruise Key West
Pedal, pedal then bottoms up! Now is the time to book this Cycleboat Cruise Key West for your chance at an all-inclusive...
Private Key West Dolphin Sightseeing Charter
Set out on an adventure with this Key West Dolphin Sightseeing Charter. Enjoy cruising on gorgeous water within...
Private Key West Sandbar & Snorkeling Charter
Experience the beautiful Florida Keys and its lush mangroves, islands, turquoise waters, and marine life on this full...
Private 8 Hour Key West Fishing Charter (for 6 Guests)
All aboard this center console for a day of fun in the sun, fishing your hearts out with this Private 8 Hour Key West...
Private Tritoon Charter on the Barefoot One
Hang out like the locals! The shallow, clear backcountry waters of the Florida Keys sets it apart from anywhere else in...
Private Harbor Day Sail Aboard the High Tide
Cruise the scenic waters of America's southernmost city on a private day sail adventure with the professionals at Sunset...
Rum Runner Bar Boat Sunset Cruise
Enjoy a sunset cruise on the water on the best value bar boat in Key West. Cruise the gorgeous water on this Rum Runner...
Rise & Reef Snorkeling Trip With Breakfast & Unlimited Mimosas
Take an adventure into the depths to explore Florida's best reef on a snorkeling experience you will never forget! The...
Private Key West Morning Boat Charter (Up to 6 guests)
Climb aboard for a day of ultimate relaxation on this Private Key West Morning Boat Charter. Get ready to cruise away on...
Private Key West Afternoon Boat Charter (up to 6 guests)
Climb aboard for a day of ultimate relaxation on this Private Key West Afternoon Boat Charter. Get ready to cruise away...
Rum Runner Bar Boat Early Bird Cruise
Cruise the gorgeous water on the best value bar boat in Key West and give a cheers for every gorgeous sight. Perfect for...
Backcountry Paradise Private Charter - Up to 4 Guests
Take an adventure through the Florida Keys' Backcountry on a Custom Charter for up to four guests. Customize your...
Private Chill Out Lily-Pad Sail - Up to Six Guests
Live the Key West lifestyle as you set sail over calm blue waters then drop anchor and chill out on a giant floating...
Dip and Sip Afternoon Snorkel with Open Bar
Take an afternoon and plunge into the depths of Florida's coral reef for an amazing snorkeling experience. The Sandie...
Combo Dolphin and Snorkel Cruise in Key West
Climb aboard a combo snorkel and dolphin watch adventure and see the best of Key West. First head out looking for pods...
Private BYOB Sunset Sailing Excursions
Cruise the picturesque waters of Key West at sunset aboard the 33' yacht of Sunset Sail Key West. Among the most popular...
Private Charter Fishing in Key West
Climb aboard and take to the open ocean on an unforgettable Key West deep sea fishing excursion with Captain Conch...
Private Luxury Yacht Charter
Climb onboard the After Hours for a one-of-a-kind adventure through the Florida Keys with this Private Luxury Yacht...
Sunset Sail Aboard the Historic When and If
Set sail on Key West’s most elegant historic schooner, the When And If. Built in 1939 for General George Patton’s...
3/4 Day Split Charter Fishing in Key West
Venture out to sea to chase big game with an expert captain and crew. You and up to 5 other anglers will search for some...
Key West Day Trip with Glass Bottom Boat Ride
Journey to explore the southernmost city in the U.S. on a Key West Day Trip with Glass Bottom Boat Ride from Miami or...
Schooner Champagne Sunset Sail
Come along on this Champagne Sunset Sail and step into the lap of luxury. Sip, relax, and unwind aboard a gorgeous...
Wreck Dive Scuba Adventure
Visit two shipwreck locations and explore Key West's underwater treasures. Glide through the shimmering waters in search...
Harbor History Tour Key West
Soak up the idyllic seaside views on this fully narrated Harbor History Tour Key West. Climb on board for a breathtaking...
Key West Sunset Sail on America 2.0
Embark on a spectacular sunset sailing adventure off the coast of Key West in search of the famed "Green Flash"....