Key West, FL > All activities
05/10/2021 ~ 05/16/2021
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Key West Extreme Activities, Tours & Attractions

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
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
Do It All Water Sports Adventure Package with Parasailing

Do It All Water Sports Adventure Package with Parasailing

354 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
Key West Premium Head Boat Fishing Experience

Key West Premium Head Boat Fishing Experience

New to TripShock
Duration4 Hrs.
Head out on the water for a fishing adventure you will never forget! This party boat fishing charter offers a premium...

New to TripShock

from
$89
Sunset Cycleboat Cruise Key West

Sunset Cycleboat Cruise Key West

1 rating
Duration2.5 Hrs.
Pedal, pedal then bottoms up! Now is the time to book this Sunset Cycleboat Cruise in Key West for your chance at an...
It was a great experience and highly recommend.
from
$45
Island Hopper Speedboat Excursion for Two

Island Hopper Speedboat Excursion for Two

8 ratings
Duration2.5 Hrs.
Are you looking for the best kept secret in Key West?! If so, then hop in your own personal, mini speedboat and follow...
The best f in time I ever had in Key west . Can’t wait to do it again . That was my 68 birthday present to myself . Now I want to buy one of those ocean going sports car boats . Seriously. RC Catskill NY
The staff and crew were awesome! I accidentally booked wrong time and was able to fix it easily, even though it was a very busy Saturday. Ride was amazing! The highlight of our trip for my husband, and we did some awesome things. Definitely recommend for anyone who loves speed and boating, snorkeling and exploring!!
It was awesome adventure!! Our guide was amazing and definitely something I would do again!!
from
$168
Jet Ski Island Tour from Parrot Key

Jet Ski Island Tour from Parrot Key

2 ratings
Duration1.5 Hrs.
FREE SHUTTLE ON THE ISLAND
Take a thrilling ride around the beautiful Key West by jet ski. Zip through the emerald waters and forget about your...

New to TripShock

from
$150
Key West Parasailing Adventure

Key West Parasailing Adventure

5 ratings
Duration1 Hr.
Soar above an island paradise on a tropical breeze with a Key West Parasailing Adventure. Enjoy miles of breathtaking...
Beautiful ride with a professional and hilarious crew! Take this trip if in Key West! Fury makes it more than just a parasail ride.
Captain Alex and first mate Dan were very pleasant and hilarious! They made our experience so much fun especially for my 10 year old niece, Saylor. She loved it so much that she wanted to do it again once the boat returned. This is an memory she will forever carry and we’re thankful for that.
from
$80
Key West Sunset Sail on America 2.0

Key West Sunset Sail on America 2.0

30 ratings
Duration2 Hrs.
Embark on a spectacular sunset sailing adventure off the coast of Key West in search of the famed "Green Flash"....
We loved our time on the sunset cruise! Staff was exceptional and the captain was awesome and informative! The sunset was stunning! Highly recommend this trip!
Easy process to make reservations and we had a great time celebrating our 35th anniversary on the America 2.0!!
The WHOLE CREW was great. What a awesome experience. Totally enjoyed every moment. Wished it would have never ended. You should think about charging for the ride up to NewYork City when they run the schooner up to the other port.
from
$96
Jet Ski Island Tour of Key West from Casa Marina

Jet Ski Island Tour of Key West from Casa Marina

8 ratings
Duration2 Hrs.
Explore beautiful Key West as you circumnavigate its tropical waters on this Jet Ski Tour from Casa Marina Resort. This...
First time on jet skis for both of us and what a great time! The staff was very knowledgeable and made sure we all had a great time. I would highly recommend.
Taking a jet ski tour at sunset was already a one of a kind experience, but the staff really made it superior. From the owner to the guides, I would heavily suggest this tour. Great price and an epic adventure! So much fun!
Best jet ski tour we ever experienced
from
$139
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
Full Day Watersports Adventure with Breakfast & Lunch
This all-inclusive trip includes sailing, jet skis, parasailing, banana boat rides, snorkeling, kayaking, and more!...
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....
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...
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....
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...
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, 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 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...
Beach Pass Watersports Package with Parasailing
Enjoy everything Smathers Beach has to offer with this Beach Pass Watersports Package with Parasailing. Capture the...