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Top Key West Outdoor Activities

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Key West Tours

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Key West Mangrove Kayak Eco Tour

Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key …More

4.9 (2,370)

Key West Mangrove Kayak Eco Tour

Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key...

2 hours • Free Cancellation
4.9 (2,370)
from
$80
Key West Party Boat Fishing Charter

Our Key West Party Boat Fishing Charter is great for an affordable day on the water with friends and family enjoying the best Key West …More

4.7 (147)

Key West Party Boat Fishing Charter

Our Key West Party Boat Fishing Charter is great for an affordable day on the water with friends and family enjoying the best Key West...

6 hours (approx.) • Free Cancellation
4.7 (147)
from
$70
Key West Private Luxury Pro Fishing Yacht Charter (up to 41 passengers)

Cool Destinations brings you the ultimate Private Deep Sea Fishing Charter experience with a classic 63-foot sportfishing boat that can show 41 day-trip guests a …More

Likely to Sell Out
Likely to Sell Out
4.9 (19)

Key West Private Luxury Pro Fishing Yacht Charter (up to 41 passengers)

Cool Destinations brings you the ultimate Private Deep Sea Fishing Charter experience with a classic 63-foot sportfishing boat that can show 41 day-trip guests a...

4-12 hours (approx.) • Free Cancellation
4.9 (19)
from
$1,700
Shark and Wildlife Viewing Adventure in Key West

This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to …More

Likely to Sell Out
Likely to Sell Out
5.0 (3,287)

Shark and Wildlife Viewing Adventure in Key West

This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to...

2 hours • Free Cancellation
5.0 (3,287)
from
$99
Key West Safari Eco Sandbar Tour Adventure with Snorkeling

Explore Key West in a fun and unique way! Avoid the crowds on this exciting snorkel safari adventure and captain your own speedboat through 28 …More

4.7 (220)

Key West Safari Eco Sandbar Tour Adventure with Snorkeling

Explore Key West in a fun and unique way! Avoid the crowds on this exciting snorkel safari adventure and captain your own speedboat through 28...

2 hours 30 minutes • Free Cancellation
4.7 (220)
from
$197
Guided Clear Kayak Eco-Tour Near Key West

100% Clear Kayaks: Unlike traditional kayaks, ours are completely see-through. As you paddle, you'll have a front-row seat to the vibrant marine life beneath the …More

Likely to Sell Out
Likely to Sell Out
4.9 (727)

Guided Clear Kayak Eco-Tour Near Key West

100% Clear Kayaks: Unlike traditional kayaks, ours are completely see-through. As you paddle, you'll have a front-row seat to the vibrant marine life beneath the...

2 hours • Free Cancellation
4.9 (727)
from
$79
Sunset Sail Cruise in Key West

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's …More

Likely to Sell Out
Likely to Sell Out
5.0 (290)

Sunset Sail Cruise in Key West

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...

2 hours • Free Cancellation
5.0 (290)
from
$95
Key West Island Adventure: Sandbar, Kayak & Paddleboard Excursion with Sunset Option

Enjoy life like a Key West local with a picnic play day on the calm, clear waters and pure white sands of a Backcountry sandbar …More

Likely to Sell Out
Likely to Sell Out
4.9 (616)

Key West Island Adventure: Sandbar, Kayak & Paddleboard Excursion with Sunset Option

Enjoy life like a Key West local with a picnic play day on the calm, clear waters and pure white sands of a Backcountry sandbar...

3.5 Hours (approx.) • Free Cancellation
4.9 (616)
from
$120
Key West Mini Catamaran Eco Tour

Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you …More

Likely to Sell Out
Likely to Sell Out
4.8 (181)

Key West Mini Catamaran Eco Tour

Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you...

1 hour 30 minutes • Free Cancellation
4.8 (181)
from
$285
Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and …More

4.9 (569)

Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and...

4 hours • Free Cancellation
4.9 (569)
from
$143
Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks

Join us for the ultimate sandbar adventure in Key West. This trip combines the best activities Key West has to offer. We will cruise out …More

4.9 (421)

Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks

Join us for the ultimate sandbar adventure in Key West. This trip combines the best activities Key West has to offer. We will cruise out...

5 hours • Free Cancellation
4.9 (421)
from
$161
Sandbar Adventure Cruise in the Florida Keys

Discover the enchanting beauty of the Florida Keys with Island Girls Excursions. This adventure combines relaxing sandbar experiences with stunning sunset cruises. Unwind on your …More

Likely to Sell Out
Likely to Sell Out
4.9 (15)

Sandbar Adventure Cruise in the Florida Keys

Discover the enchanting beauty of the Florida Keys with Island Girls Excursions. This adventure combines relaxing sandbar experiences with stunning sunset cruises. Unwind on your...

4 hours • Free Cancellation
4.9 (15)
from
$87
Florida Key West Self-Guided Driving Tour (7 Mile Bridge)

Discover the beautiful Florida Keys with a self-guided audio tour! This 100-mile drive stretches from Key Largo, the first island off the Florida coast, all …More

4.7 (69)

Florida Key West Self-Guided Driving Tour (7 Mile Bridge)

Discover the beautiful Florida Keys with a self-guided audio tour! This 100-mile drive stretches from Key Largo, the first island off the Florida coast, all...

2 to 3 hours • Free Cancellation
4.7 (69)
from
$17
Key West Parasailing: Ideal For Cruise Ship & Downtown Guests

This location was carefully selected to offer convenience to all guests arriving on cruise ships or those looking to parasail downtown. Situated a mere 5-minute …More

4.9 (53)

Key West Parasailing: Ideal For Cruise Ship & Downtown Guests

This location was carefully selected to offer convenience to all guests arriving on cruise ships or those looking to parasail downtown. Situated a mere 5-minute...

1 hour • Free Cancellation
4.9 (53)
from
$64
Florida Keys Nature & History Tour from Key West

With your friendly and knowledgeable tour guide, this 4 Hour VIP Tour of the South Keys promises to amaze you. En route, you’ll learn the …More

4.9 (117)

Florida Keys Nature & History Tour from Key West

With your friendly and knowledgeable tour guide, this 4 Hour VIP Tour of the South Keys promises to amaze you. En route, you’ll learn the...

4 hours • Hotel pickup offered • Free Cancellation
4.9 (117)
from
$85
Dry Tortugas National Park Day Trip by Catamaran from Key West

Explore beautiful tropical beaches on this full-day catamaran trip from Key West to Dry Tortugas National Park. The Dry Tortugas islands were discovered by Ponce …More

4.7 (442)

Dry Tortugas National Park Day Trip by Catamaran from Key West

Explore beautiful tropical beaches on this full-day catamaran trip from Key West to Dry Tortugas National Park. The Dry Tortugas islands were discovered by Ponce...

10 hours
4.7 (442)
from
$245
Key West Sunset Sail Aboard Legendary Schooner Appledore

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern …More

5.0 (364)

Key West Sunset Sail Aboard Legendary Schooner Appledore

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

2 hours • Free Cancellation
5.0 (364)
from
$89
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your …More

4.9 (114)

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your...

5 hours • Free Cancellation
4.9 (114)
from
$119
Key West's Happy Hour Sandbar & Sunset Cruise - Unlimited Drinks

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar & …More

4.6 (39)

Key West's Happy Hour Sandbar & Sunset Cruise - Unlimited Drinks

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar &...

4 hours • Free Cancellation
4.6 (39)
from
$137
Go City: Miami Explorer Pass - Choose 2, 3, 4 or 5 Attractions

Go City's Explorer pass is the best Miami pass for savings and flexibility Create your own sightseeing itinerary and gain admission to your choice of …More

4.5 (21)

Go City: Miami Explorer Pass - Choose 2, 3, 4 or 5 Attractions

Go City's Explorer pass is the best Miami pass for savings and flexibility Create your own sightseeing itinerary and gain admission to your choice of...

1 to 30 days
4.5 (21)
from
$79

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Great day trip from Key West
New York City
Dry Tortugas National Park Day Trip by Catamaran from Key West
Carlton_B, Sep 2026
Great day trip from Key West
Great boat trip, great crew, great place to visit if you like history.Tour guide named Hollywood was outstanding.
Read more
Perfect trip
New York City
Key West’s Happy Hour Sandbar & Sunset Cruise – Unlimited Drinks
Brandy_C, Sep 2026
Perfect trip
First time me and my husband went on a sunset cruise to a sandbar. The crew was fantastic. We were able to see dolphins along the way. We also saw the top of a hammerhead shark coming up out of the water near the sandbar where we anchored. It was amazing swimming at the sandbar. There were floating lilypads, snorkel gear, and noodles you could use. The drinks, food and service were great. The boat ride out, sunset, and boat ride back was great with beautiful scenery. Highly recommend!
Read more
A tranquil excursion in paradise
New York City
Key West Mangrove Kayak Eco Tour
charlestrapp1962, Sep 2026
A tranquil excursion in paradise
My guide Rachel was dynamic, effervescent and very knowledgeable. I think her standing position on her paddleboard allowed her to see things that I had a hard time viewing but immersing myself in the mangroves through the channels was an awesome experience. Her presentation of the history of Key West was given in a very fun manner and Rachel made sure to engage everyone in the group. Our tour ended two minutes too late as we were hit with driving rain. Or could it be that we ended at exactly the right time to experience the true Key West experience. It was money well spent and definitely something I would do again for a relaxing experience.
Read more
Exceptional Adventure
New York City
Dry Tortugas National Park Day Trip by Catamaran from Key West
George_M, Sep 2026
Exceptional Adventure
2 hour peaceful ferry boat ride to Fort Jefferson. We then do the 30 minutes fort tour and spent another 30 minutes walking along the top of the fort. We then got snorkeling gear and snorkeled at the piers on the north post. We then swam around the outside of the fort and hit the piers in the south beach. There were a ton of fish at both sets of piers. I highly recommend snorkeling and swimming out to the old piers on both beaches. Do the short tour as it is very informative. The fort is incredible and unbelievable to see and the snorkeling is great and I recommend this as A MUST DO in Key Wedt
Read more
Unique Kayaking Experience
New York City
Guided Clear Kayak Eco-Tour Near Key West
Culture54981487604, Sep 2026
Unique Kayaking Experience
Such a fun experience with Get Up And Go Kayaking! The clear kayaks were so cool because you could see right through the water while kayaking through the mangroves. Our guide was friendly, knowledgeable, and made the tour really enjoyable.
Read more
Awesome eco tour
New York City
Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling
Ben_R, Sep 2026
Awesome eco tour
Knowledgeable and experienced captain and crew. Great food, great tour. Great respect for nature. Family friendly.
Read more
Kayaking the mangroves
New York City
Key West Mangrove Kayak Eco Tour
Kristen_E, Sep 2026
Kayaking the mangroves
We had a beautiful kayak tour of the mangroves with Tall Rachel today. She shared her knowledge and respect for this beautiful area and habitat. She had a great eye and spotted a manatee, ray, cormorants and heron and green sea turtle for us. It was a perfect two hour trip!
Read more
A beautiful night!
New York City
Key West Sunset Sail Aboard Legendary Schooner Appledore
Lisa_M, Sep 2026
A beautiful night!
This tour was amazing! The boat was beautiful and the crew amazing!! My husband and I took this and very happy we did it made our key west trip so memorable!!!
Read more
Wonderful crew. The...
New York City
Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks
Rachel_K, Sep 2026
Wonderful crew. The...
Wonderful crew. The snacks were good so were the drinks. The sandbar was beautiful and there was a great atmosphere
Read more
Would 100% Recommend!!!
New York City
Shark and Wildlife Viewing Adventure in Key West
G6967VXmaricarmenp, Sep 2026
Would 100% Recommend!!!
Amazing one of a kind experience!!! 😃
Read more
Great morning with the sharks and dolphins!
New York City
Shark and Wildlife Viewing Adventure in Key West
Yvette_P, Sep 2026
Great morning with the sharks and dolphins!
The sharks were awesome! Captain and mate are very knowledgeable on the seas and it’s sea life. It was also a lovely ride. You will see sharks! Oh yeah and dolphins.
Read more
Awesome trip
New York City
Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks
Jessie_G, Sep 2026
Awesome trip
Logan, Jordan and Claire were excellent. Definitely recommend this place. Try it out when you visit Key West!
Read more
Jodie was great
New York City
Guided Clear Kayak Eco-Tour Near Key West
K4334JDlukam, Sep 2026
Jodie was great
I had a great time with Jodie on the kayak ecotour in key west!
Read more
Sandbar cruise
New York City
Sandbar Adventure Cruise in the Florida Keys
lisawW6430ZW, Sep 2026
Sandbar cruise
The sandbar cruise was one of the best experiences on our trip to the keys!
Read more
Sooo much fun
New York City
Key West Mini Catamaran Eco Tour
Tara_K, Sep 2026
Sooo much fun
Our guide was Jo Jo and he was great. We had a great time would definitely recommend doing it. We got to see a manatee.
Read more
Really fun day for two couples
New York City
Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling
T9378OZbillb, Sep 2026
Really fun day for two couples
Great time spent with a knowledgeable and fun Captain. So much fun for all experience level snorkelers. Ask for Captain Kristen.
Read more
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