Key West, FL > All activities
05/12/2021 ~ 05/17/2021
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Top Key West attractions, tours & rentals

Morning Reef Snorkel and Sail in Key West
$50
$42
Duration3 Hrs.
Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings
$80
$74
Duration2.5 Hrs.

Things to do in Key West, FL

Key West Sunset Dinner Cruise

Key West Sunset Dinner Cruise

203 ratings
Duration2 Hrs.
If you are looking to make memories on a glorious Key West sunset as you dine and enjoy drinks with your loved ones,...
My friend and I had a great time at the dinner cruise..we met some nice people when we were waiting to board the boat. The food was good and well prepared. Will do again the next time we are in Key West.
I felt like this was worth the price. Everyone was friendly, the food was good and then sunset was nice!
Four of us ladies had a blast on the Sunset Dinner Cruise! Everything was perfect! Very cute and friendly bartenders who made fantastic drinks! Our new favorite drink is a Key Lime Martini!
from $70
$69
Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

114 ratings
Duration2 Hrs.
Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local...
The sunset sail was one of our favorite highlights to Key West!! Staff and crew were delightful!! Drinks and food were awesome and live music the perfect touch!! And then there is the sunset!! WOW!! We even got to see a few dolphins!! Best way to spend our last night in Key West!
Great hors d’oeuvres and appreciated the unlimited bar service.
Good food. Good beverages. On time launch and return. Friendly staff. Overall no one of the best activities we experienced in KW.
from $70
$64
Smathers Beach Parasailing Adventure

Smathers Beach Parasailing Adventure

27 ratings
Duration1 Hr.
Come parasail the ocean blue skies of Key West where you’ll get a bird's eye view of Key West and Smathers Beach from...
My daughter and I tried parasailing for the first time ever and were pretty nervous at first! The guys on our boat were so helpful and accommodating and FUN!!!!! We had a great time!
I loved it ! Very fun and professional! I will be going back again!
Best experience ever. I’d do it all over again in a heartbeat!!!!
from
$70
Key West Party Boat Fishing Trip (6 Hour)

Key West Party Boat Fishing Trip (6 Hour)

10 ratings
Duration6 Hrs.
If you're looking for the best angling adventure in Key West, then this 6 hour Party Boat Fishing Trip is the one for...
Great experience, Captain put us on the fish. Whole family went and had a blast.
Everything was good from beginning to end. Calling & booking with TripShock was easy & the rep was very pleasant & thorough. The crew from Gulfstream was awesome.
Caption and crew did an excellent job of making the trip enjoyable for both our 11 year daughter and us, parents. We fished multiple locations and caught multiple species of fish. The galley food was a big hit with our daughter. Overall it was a great time. We recommend others to take a trip out when in Key West.
from
$67
Rum Runner Bar Boat Castaway Cruise

Rum Runner Bar Boat Castaway Cruise

3 ratings
Duration1.5 Hrs.
Enjoy this Rum Runner Bar Boat Castaway Cruise and get out on the water for some fun to last the summer through. Cruise...
It was great. Does not have space for lots of people so that made it perfect. Sometimes you book a boat adventure and there is so many people your constantly bumping into them....Captain was super nice. I'll definitely do it again
Entertaining and beautiful scenery!!!
from
$35
2 Hour Private Sunset Cruise on a Tiki Bar Boat

2 Hour Private Sunset Cruise on a Tiki Bar Boat

1 rating
Duration2 Hrs.
If you are looking for a way to float away the day, then this 2 Hour Private Sunset Cruise on a Tiki Bar Boat is the...

New to TripShock

from
$425
Glass Bottom Boat Reef & Eco Tour

Glass Bottom Boat Reef & Eco Tour

16 ratings
Duration2 Hrs.
Climb aboard for an adventure through the most diverse underwater ecosystem in the United States with the Glass Bottom...
The Coral Reef was Great the Sunset was absolutely Breathtaking ✨
The crew was great - boat was in excellent condition. Was a pretty cool trip - even though water was a bit rough, we were still able to have some great sights
We had a great time on the ride! Marta was very knowledgeable and we very much enjoyed our trip to the barrier reef.
from
$50
Do It All Water Sports Adventure Package with Parasailing

Do It All Water Sports Adventure Package with Parasailing

355 ratings
Duration6 Hrs.
A $350 VALUE FOR $139!
Don't miss your chance to “Do it All” with a daylong Watersport Adventure Package with Parasailing in Key West. This...
I am super impressed with the 9am reef snorkel we had today! the water was so clear, the captain was a great driver not really Rocky and the weather...
Did my first dinner cruise and it was excellent!! Capt. Carl and crew made for a wonderful experience in spite of cold weather and the Covid protocols. Was...
We Decided to go on a sunset dinner cruise the last night of our trip. We were pleasantly surprised. The crew was nice Ross Brown who entertained was...
from
$150
Full Day Sail, Snorkel and Kayak Excursion

Full Day Sail, Snorkel and Kayak Excursion

11 ratings
Duration6.5 Hrs.
Get out on the water and experience nature at her finest with Full Day Sail, Snorkel and Kayak Excursion complete with...
Fantastic time, great weather and staff was amazing
Great time! Great experience! The trip was ran very well and the crew was excellent! We will be back!
Relaxing and adventurous at the same time. Friendly crew!
from
$120
Key West Sunset Celebration Walking Tour with Cocktails

Key West Sunset Celebration Walking Tour with Cocktails

New to TripShock
Duration2.5 - 3 Hrs.
You are invited to take an exclusive cocktail & food tasting tour on the Waterfront in Downtown Key West! Step into the...

New to TripShock

from
$69
Key West Premium Head Boat Fishing Experience
Head out on the water for a fishing adventure you will never forget! This party boat fishing charter offers a premium...
Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings
Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Dolphin Watch Sunset...
Key West Pontoon Rental
Toss your worries away and book yourself and crew on this Key West Pontoon Rental. With two size options, and your...
Key West Tropical Bike Tour
Discover Key West through the eyes of a local named Lloyd on an unforgettable Tropical Bike Tour. Take a leisurely ride...
Triple Combo Snorkeling, Dolphin, and Sunset Cruise
This triple combo tour gives you three amazing experiences in one package. Watch pods of local dolphins playing in their...
Sunset Cycleboat Cruise Key West
Pedal, pedal then bottoms up! Now is the time to book this Sunset Cycleboat Cruise in Key West for your chance at an...
Private Key West Walking Tour
Experience the remarkable and historic Key West by foot while observing the sights and embracing the unique vibe of this...
Island Hopper Speedboat Excursion for Two
Are you looking for the best kept secret in Key West?! If so, then hop in your own personal, mini speedboat and follow...
Jet Ski Island Tour from Parrot Key
Take a thrilling ride around the beautiful Key West by jet ski. Zip through the emerald waters and forget about your...
Champagne Sunset Catamaran Cruise
Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted...
8 Hour Key West Boat Rental
Cast your cares to the wind and book you and your crew on this Key West Boat Rental. With multiple size options, you can...
Day Sail Aboard Schooner America 2.0
Explore the high seas in style on the Schooner America 2.0, namesake of the first sailboat to win the America's Cup in...
Key West Parasailing Adventure
Soar above an island paradise on a tropical breeze with a Key West Parasailing Adventure. Enjoy miles of breathtaking...
Sunset Sip and Sail with Open Bar and Live Music
Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this...
Bone Island Haunted Pub Crawl & Ghost Tour
Are you ready to experience one of the top 5 haunted places in America? If so, then look no further, this Bone Island...
Wind and Wine Sunset Sail
Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around...
Small Group Key West Food Tasting & Culture Walking Tour
Meet your fellow foodies in Old Key West and set off to explore the mouthwatering tastes of the region. Skip the tourist...
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"....
Jet Ski Island Tour of Key West from Casa Marina
Explore beautiful Key West as you circumnavigate its tropical waters on this Jet Ski Tour from Casa Marina Resort. This...
Reef Dive or Snorkel Excursion
Experience tropical diving or snorkeling and swim with marine wildlife on a thrilling excursion to two different reef...
Half Day Split Charter Fishing in Key West
Climb aboard a 34' Crusader and take to the ocean blue on a deep sea fishing charter for up to 6 guests. On this...
Key West Parasailing
Prepare to be astonished as you fly 300 feet in the air above Key West. Experience the still tranquility while you float...
Key West Kayak Eco-Tour
Join in on this guided Key West Kayak Eco-Tour and paddle at a relaxed pace through the crystal clear water of Key...
Private Cycleboat Cruise Key West
Pedal, pedal then bottoms up! Now is the time to book this Private Cycleboat Cruise Key West for your chance at an...
Live Music Sunset Cruise with Cocktails Included
Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise. Experience...
Private Fishing Charter in Key West
Climb aboard a 34' Crusader and take to the ocean blue on a Private Fishing Charter in Key West for up to 6 guests. Take...
Original Key West Pub Crawl
Take a tipsy stroll through Key West's famous downtown and its boisterous bars. You will get to experience five...
Sunset Snorkel Sail with Open Bar & Live Music
Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Sandie Cat...
Morning Reef Snorkel and Sail in Key West
Begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. First, you’ll sail...
Seabreeze Sunset Harbor Cruise with Wine and Beer
Escape the hustle and bustle and experience a breathtaking Key West sunset with a Seabreeze Sunset Harbor Cruise. Your...
Downtown Parasailing Adventure
If you are looking for something exciting to do over downtown Key West, then this is the adventure for you. Parasail the...
4 Hour Key West Boat Rental
Cast your cares to the wind and book you and your crew on this Key West Boat Rental. With multiple size options, you can...
4 Hour Private Sandbar Cruise on a Tiki Bar Boat
Climb on a floating tiki bar boat for a truly unique Key West sandbar experience. Enjoy a seat at the bar as you journey...
Kayak Rental at the Reach Resort
Be your own guide as you explore the sapphire blue waters of Key West in a kayak rental from Barefoot Billy's. With...
Sunset Snorkel & Sail with Rum & Reggae Included
Leave the land behind for an evening of snorkeling and Reggae music on this Sunset Snorkel & Sail with Rum & Reggae...
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...
Jet Ski Tour of Key West from Marriott Beachside
Race around the tropical waters of beautiful Key West on a Jet Ski Island Tour. An exciting, high-speed tour around the...
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...
Paddleboard Rentals at Casa Marina
Feel like your walking on water as you take in the beauty of Key West on your personal paddleboard. Glide over sparkling...
Early Bird Jet Ski Island Tour from Parrot Key
See Key West from the water on this Early Bird Jet Ski Island Tour from Parrot Key. Zip around on some new jet skis and...
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...
Jet Ski Island Tour of Key West from Cow Key Marina
Treat yourself to an action-packed, 28 mile Jet Ski tour among the sparkling waters of Key West and beyond. Join...
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...
Private 6 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 6 Hour Key West...
Do It All Water Sports Adventure Package
Don't miss your chance to “Do it All” with a day-long Watersport Adventure Package in Key West. This all-inclusive...
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...
Guided Old Town Bike Tour of Key West
Slow down and explore the best from Old Key West on a guided bicycle tour! This leisurely ride will teach you all about...
Java Cat Sail, Kayak, & Snorkel Half Day Eco Tour
Experience the unbridled beauty of the Keys' on this Java-Cat Sail, Kayak and Snorkel Half Day Eco Tour in Key West....
Private Sunset Cycleboat Cruise Key West
Pedal, pedal then bottoms up! Now is the time to book this Private Sunset Cycleboat Cruise Key West for your chance at...
Tiki Cocktails & Foodie Pub Crawl of Key West
Sip, stroll, and party your way through Old Key West as you and a troupe of other free-spirited beverage enthusiasts...
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...
Mallory Square Hydrobike Sunset Tour
Witness a sunset from one of the most sought out vantage points on the island, Mallory Square, but do it from the water...
Private Snorkel and Sunset Sail Excursion
Climb aboard and set out on a private snorkel and sunset sail. You'll get the best of both worlds as you glide across...
Double Dip: 2 Stop Snorkel Adventure
Experience snorkeling in the Florida Keys on an adventure like no other. Explore the crystal clear waters on this...
Castaway Island Hydrobike Tour
Escape the crowds and enjoy the tropics on this unique, guided island tour on your very own hydrobike! Similar to a...
Half Day Deer & Wildlife Tour from Key West
The only trip of its kind in Key West, the Half Day Key Deer tour, lets you travel in comfort across Overseas Highway as...
Morning Half Day Sail, Snorkel, and Kayak Excursion
Get out early and experience nature at its finest with a half day island adventure complete with sailing, kayaking, and...
Coral Reef Snorkeling Catamaran Trip with Margaritas included
Experience the best afternoon you'll find on the Straits if Flofida Keys by snorkeling this gorgeous coral reef. Climb...
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...
Historic Seaport Food Tasting & Cultural Walking Tour
Discover the incredible flavors of Key West's best Caribbean and seafood as...
Ultimate Water Sport Combo Package with Breakfast & Lunch Buffet
Embark on an all day water excursion that includes breakfast, lunch, and unlimited water sports for you and your whole...
Combo Dolphin Watch & Snorkel Tour with Beer & Wine
Take a voyage through the crystal clear water of Key West on a Combo Dolphin Watch & Snorkel Tour. Climb aboard a...
Full Day Watersports Adventure with Breakfast & Lunch
This all-inclusive trip includes sailing, jet skis, parasailing, banana boat rides, snorkeling, kayaking, and more!...
Island Snorkel & Kayak Adventure
Experience the magic of the Keys as you explore the backcountry on this Island Snorkel & Kayak or Paddleboard Adventure....
Guided Backcountry Paddle Tour
Let Key West Eco Tours pick you up for a Guided Backcountry Paddle Tour of lush island mangroves. Choose from a...
Beach Pass Watersports Package with Beach Chairs and Umbrella
Enjoy everything Smathers Beach has to offer with this Beach Pass Watersports Package with Beach Chairs and Umbrella....
Private Tiki Bar Adventure
Pick out your grass skirt and your flower lei, then set out on a fun filled Tiki Bar Adventure. The only tour of its...
The Key West Aquarium Admission Ticket
Journey under the sea without even getting wet with a Key West Aquarium Admission Ticket. The very first attraction in...
Beginner Scuba Diving Tour in the Florida Keys
Plunge into the serene waters of the Florida Keys with a private lesson and scuba diving tour. Catered specifically for...
Key West Sail, Snorkel, & Kayak Adventure
Get out on the water for an incredible day of sailing, kayaking, and snorkeling in one awesome package on this Key West...
Escape Room Experience
Gather up your friends, and see if you have what it takes in an Escape Room experience in Key West. Piece together...
Old Town Trolley Tours Key West
Step on the Old Town Trolley for a Tour of Key West and watch its history come alive. Ride along enjoying the city's top...
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...
TripShock Gift Card
Give the gift of lasting memories with a TripShock gift certificate! Let the recipient choose an adventure from top...
Key West Sailing, Kayak, & Dolphin Watching with Breakfast and Lunch
This fun-filled Key West tour combines three awesome adventures into one package. Enjoy a day of sailing, dolphin...
Miami, Fort Lauderdale, & Key West Unlimited Sightseeing Day Pass
Get your ticket to experience the best of Miami, Fort Lauderdale, and Key West with an Unlimited Sightseeing Day Pass....
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...
Hop On Hop Off Conch Tour Train Key West
Learn the legacy of the Old Town from the Conch's themselves on a Conch Tour Train in Key West. When you come on board...
Ghosts and Gravestones Tour Key West
Climb on board for a bone-chilling Ghosts and Gravestones Tour of Key West. Journey down dark narrow streets, past 19th...
Key West Day Trip From Miami
Take a journey from Miami, across the Overseas Highway, to beautiful Key West on a day trip from Miami. Hop on a luxury...
Florida Keys & Miami Explorer Pass
The Florida Keys & Miami Explorer Pass gives you the most bang for your buck on a variety of sweet South Florida...
Morning Coral Reef Snorkel Adventure & Catamaran Cruise
Experience some morning snorkeling in the sparkling waters of the Florida Keys on this Morning Coral Reef Snorkel...
Private Dolphin Research Center Adventure from Key West
Travel up the Keys to visit the Dolphin Research Center and make exciting stops along the way on this full day...
Afternoon Reef Snorkel and Sail
Immerse yourself in the tropical waters of Key West when you set out on a snorkel and sailing adventure. Watch swarms of...
Key West Shipwreck Treasures Museum Admission Ticket
See the lost treasures of old with an admission ticket to the Key West Shipwreck Treasures Museum. Home to over 400...
Truman's Little White House Admission Ticket
Discover Florida's only presidential site with an admission ticket to Truman's Little White House. Built in 1890 as the...
Private Luxury Yacht Charter
Climb aboard for a leisurely adventure through the Florida Keys with this Private Luxury Yacht Charter. Experience the...
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...
Private Up the Keys Adventure to Aquarium Encounters
Visit Aquarium Encounters and see the best the Keys has to offer on this full day adventure with Up the Keys Tours....
3/4 Day Split Charter Fishing in Key West
Climb aboard a 34' Crusader and take to the ocean blue on a deep sea fishing charter for up to 6 guests. On this 3/4 day...
Key West Double Rider Scooter Rentals
Strike out and explore Key West on a double rider scooter rental. Soak up the sun and delight in the breeze as you...
Jet Ski Tour of Key West from The Reach Resort
Explore beautiful Key West as you circumnavigate its tropical waters on this Jet Ski Tour. This exciting adventure...
Miami to Key West Day Trip & Snorkel Combo
Escape from Miami to Key West and enjoy a snorkeling booze cruise. Your journey begins on a luxury motor coach waiting...
Miami, Fort Lauderdale, & Key West Unlimited Sightseeing Flex Pass
Miami, Fort Lauderdale, and Key West are yours to explore with an Unlimited Sightseeing Flex Pass. Enjoy top activities...
Day Trip to Key West from Miami or Ft. Lauderdale
Escape to a tropical paradise with a Day Trip to Key West from Miami or Ft. Lauderdale. Climb on board and enjoy the...
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...
Key West Overnight Trip from Miami or Ft. Lauderdale
Hop on the bus and journey to charming Key West on this Overnight Trip from Miami or Ft. Lauderdale. Enjoy a comfortable...
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...
Day Trip to Key West & Conch Train Tour from Miami or Ft. Lauderdale
Get away to the tropics today with a Day Trip to Key West and Conch Train Tour. Relax and take in the coastal scenery as...
Day Trip to Key West & Trolley Tour from Miami or Ft. Lauderdale
Escape to a magical place with Caribbean flair on a Day Trip to Key West and Trolley Tour. Take in the coastal sights as...
Wreck Dive Scuba Adventure
Visit two shipwreck locations and explore Key West's underwater treasures. Glide through the shimmering waters in search...
Day Trip to Key West from Miami or Ft. Lauderdale with Parasailing
Escape to a tropical paradise on a Day Trip to Key West from Miami or Ft. Lauderdale with Parasailing. Journey through...
Bugeye Schooner Backcountry Eco Tour
Have you ever wanted to take the wheel or hoist the sails of a real schooner? If so, here's your chance! This half-day...
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 Day Trip & Snorkeling Tour From Miami or Ft. Lauderdale
Take a journey South to explore with this Key West Day Trip and Snorkeling Tour from Miami or Ft. Lauderdale. On a...
Beach Pass Watersports Package with Parasailing
Enjoy everything Smathers Beach has to offer with this Beach Pass Watersports Package with Parasailing. Capture the...