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Top Key West Tours, Tickets & Activities

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Key West Tours

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Key West 4 Seater EZGO Golf Cart Rental

Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and …More

Likely to Sell Out
Likely to Sell Out
4.9 (1,361)

Key West 4 Seater EZGO Golf Cart Rental

Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and...

3 hours and up • Free Cancellation
4.9 (1,361)
$100
$99
Key West 4 Seater Electric Car Rental

Cruise Key West with family or friends! Four people can get around town in comfort and ease with the smooth, silent GEM 4-seater electric car …More

Likely to Sell Out
Likely to Sell Out
4.9 (1,110)

Key West 4 Seater Electric Car Rental

Cruise Key West with family or friends! Four people can get around town in comfort and ease with the smooth, silent GEM 4-seater electric car...

3 hours and up • Free Cancellation
4.9 (1,110)
$100
$99
Key West Original Island Jet Ski Tour

Get into some wet & wild watersports excitement on the best Key West jet ski tour around – a 90-minute adventure featuring 28 miles of …More

Likely to Sell Out
Likely to Sell Out
4.9 (3,085)

Key West Original Island Jet Ski Tour

Get into some wet & wild watersports excitement on the best Key West jet ski tour around – a 90-minute adventure featuring 28 miles of...

1.5 Hours • Free Cancellation
4.9 (3,085)
$170
$120
Key West Wind & Wine Sunset Sail

Wind & Wine has been the #1 rated sunset sail on Cool Destinations for over a decade. In our opinion, this is the best wine …More

Likely to Sell Out
Likely to Sell Out
5.0 (1,703)

Key West Wind & Wine Sunset Sail

Wind & Wine has been the #1 rated sunset sail on Cool Destinations for over a decade. In our opinion, this is the best wine...

2 hours (approx.) • Free Cancellation
5.0 (1,703)
$115
$99
Key West Split Fishing Charter

On a Key West Split Fishing Charter, you save by dividing the charter cost between several people. Book your Key West split-charter fishing trip now …More

Likely to Sell Out
Likely to Sell Out
4.8 (503)

Key West Split Fishing Charter

On a Key West Split Fishing Charter, you save by dividing the charter cost between several people. Book your Key West split-charter fishing trip now...

4 or 6 hours (approx.) • Free Cancellation
4.8 (503)
$350
$200
Premium Key West Party Head Boat Fishing Experience (Max 10 Guests)

“The captain ann lewis were amazing!!!”

— Duane Langner

Economical, safe Key West fishing fun. Great inshore fishing with only 9 other guests onboard on our Premium Key West Party Head Boat Fishing Experience. …More

Likely to Sell Out
Likely to Sell Out
4.8 (249)

Premium Key West Party Head Boat Fishing Experience (Max 10 Guests)

Economical, safe Key West fishing fun. Great inshore fishing with only 9 other guests onboard on our Premium Key West Party Head Boat Fishing Experience....

4 hours (approx.) • Free Cancellation
4.8 (249)
$109
$99
Key West PADI® Discover Scuba 1-day Resort Course

The is the absolute best way for a person to experience diving. Great for those who want to try scuba diving in Key West. …More

Likely to Sell Out
Likely to Sell Out
4.9 (146)

Key West PADI® Discover Scuba 1-day Resort Course

The is the absolute best way for a person to experience diving. Great for those who want to try scuba diving in Key West....

9 hours (approx.) • Free Cancellation
4.9 (146)
$269
$229
Private Key West Deep Sea Fishing Charter

Experience the thrill of a Key West deep sea fishing adventure on a hunt for trophy game fish with your own Key West fishing charter …More

Likely to Sell Out
Likely to Sell Out
4.9 (268)

Private Key West Deep Sea Fishing Charter

Experience the thrill of a Key West deep sea fishing adventure on a hunt for trophy game fish with your own Key West fishing charter...

4, 6 or 8 hours (approx.) • Free Cancellation
4.9 (268)
$1,000
$900
Key West Original Full-Day Watersports Adventure

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the …More

Special Offer
Special Offer
4.9 (739)

Key West Original Full-Day Watersports Adventure

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the...

6 hours (approx.) • Free Cancellation
4.9 (739)
$200
$169
Key West Parasailing Adventure

Float high above and parasail the Atlantic waters for a bird’s eye view of Florida’s beautiful Key West, the Southernmost Point in the US. This …More

Special Offer
Special Offer
4.9 (1,015)

Key West Parasailing Adventure

Float high above and parasail the Atlantic waters for a bird’s eye view of Florida’s beautiful Key West, the Southernmost Point in the US. This...

1 Hour • Free Cancellation
4.9 (1,015)
$85
$64
Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise …More

Special Offer
Special Offer
4.9 (128)

Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise...

2 hours (approx.) • Hotel pickup offered • Free Cancellation
4.9 (128)
$99
$89
Key West Scuba Diving Refresher Course & Dive

The Cool Destinations Scuba Refresher course is a safe, fun skills review perfect for Open Water divers who have been out of the water for …More

Special Offer
Special Offer
5.0 (22)

Key West Scuba Diving Refresher Course & Dive

The Cool Destinations Scuba Refresher course is a safe, fun skills review perfect for Open Water divers who have been out of the water for...

8 hours (approx.) • Free Cancellation
5.0 (22)
$229
$225
Key West Private Inshore Light Tackle Fishing Charter (up to 10+ passengers)

Enjoy a fun-filled day catching lots of fish in the calm and sheltered nearshore waters of Key West with this scenic, Family-Friendly Fishing Tour! …More

Likely to Sell Out
Likely to Sell Out
4.9 (23)

Key West Private Inshore Light Tackle Fishing Charter (up to 10+ passengers)

Enjoy a fun-filled day catching lots of fish in the calm and sheltered nearshore waters of Key West with this scenic, Family-Friendly Fishing Tour!...

4 hours (approx.) • Free Cancellation
4.9 (23)
$1,300
$1,200
Key West Full-Day Catamaran Eco Tour: Sail, Kayak and Dolphin Watch

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a …More

Special Offer
Special Offer
4.9 (558)

Key West Full-Day Catamaran Eco Tour: Sail, Kayak and Dolphin Watch

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a...

6 hours (approx.)
4.9 (558)
$125
$120
Key West Night 1-Tank Night SCUBA Dive

Go Key West night diving and experience nightime on the coral reef on a Cool Destinations 1-Tank Key West Night SCUBA Dive. A shallow, easy …More

Special Offer
Special Offer
5.0 (1)

Key West Night 1-Tank Night SCUBA Dive

Go Key West night diving and experience nightime on the coral reef on a Cool Destinations 1-Tank Key West Night SCUBA Dive. A shallow, easy...

2 hours 30 minutes (approx.) • Free Cancellation
5.0 (1)
$169
$149
Private Key West Morning Sail, Snorkel & Kayak Excursion

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge. …More

Special Offer
Special Offer

Private Key West Morning Sail, Snorkel & Kayak Excursion

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4 hours 30 minutes (approx.) • Free Cancellation
$2,399
$2,270
Key West Smather's Beach All Day Pass with Parasailing

The beach pass is an all-day, all-inclusive package. Buy a combo package that includes parasailing or one that includes an umbrella, chairs, and all the …More

Special Offer
Special Offer
4.7 (19)

Key West Smather's Beach All Day Pass with Parasailing

The beach pass is an all-day, all-inclusive package. Buy a combo package that includes parasailing or one that includes an umbrella, chairs, and all the...

All Day (9am - 5pm) • Free Cancellation
4.7 (19)
$109
$100
Key West PADI® Advanced Open Water Diver Scuba Certification

Go deeper into the world of Scuba with PADI® Advanced Open Water Diver certification. Expand your skills and experience, qualify for pro-level dive training. …More

Special Offer
Special Offer
5.0 (2)

Key West PADI® Advanced Open Water Diver Scuba Certification

Go deeper into the world of Scuba with PADI® Advanced Open Water Diver certification. Expand your skills and experience, qualify for pro-level dive training....

2 days (approx.) • Free Cancellation
5.0 (2)
$699
$659

Frequently Asked Questions

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

Recent tour reviews
Great way to explore!
New York City
Key West 4 Seater EZGO Golf Cart Rental
Michael L, Sep 2026
Great way to explore!
It was perfect. We were there early Sept, really hot and humid. Tough to walk very far. This is the best way to get around, go down some streets you normally wouldn't, go to restaurants you normally wouldn't, shops, etc. It's too easy.
Read more
awesome Cool Key west golf cart rental
New York City
Key West 4 Seater EZGO Golf Cart Rental
Elaine C, Sep 2026
awesome Cool Key west golf cart rental
staff very friendly and helpful. Golf cart was in excellent condition and instructions were clear. They even gave us a drive back to our cruise ship. Great job everyone!
Read more
Parasailling
New York City
Key West Parasailing Adventure
Bo H, Sep 2026
Parasailling
It was a blast the to crew members were amazing 👏, funny and all around great 👍 the only downer was the price.
Read more
A+ Cart Rental
New York City
Key West 4 Seater Electric Car Rental
Letty D, Sep 2026
A+ Cart Rental
I rented an electric cart from Key West Electric Cars in December 2025. I enjoyed getting around Key West in their quiet ride, unlike a previous visit when I rented a gas powered cart from a different vendor. The gas powered cart was so loud that we could barely hear each other speaking. On Sep.1st, 2026, I was in Key West again. I didn't give it a second thought. I rented from KWEC again. Their customer service is A+. The guys are awesome from check-in to return, and the quiet ride was top notch!! Electric carts are the best and so are the guys at Key West Electric Cars. Thanks for my second great experience!!!
Read more
PERFECT DAY!!!
New York City
Premium Key West Party Head Boat Fishing Experience (Max 10 Guests)
Duane L, Sep 2026
PERFECT DAY!!!
The captain ann lewis were amazing!!! Not only did they make this trip special for me.They did it with smiles on their face! I was able to celebrate a personal accomplishment today and after catching a 26" Grouper it made it that much special. Both the captain and lewis were eager to take pictures and celebrate the victory. Thank you for making this "the perfect day."
Read more
Key West Split Fishing Charter
New York City
Key West Split Fishing Charter
Darren H, Aug 2026
Key West Split Fishing Charter
Fantastic time. Captain Steve & Willy were amazing worked very hard and very knowledgeable putting us on the fish multiple times. We ended up with 6 fish.
Read more
Fabulous company and personal service.
New York City
Key West 4 Seater Electric Car Rental
Beth C, Aug 2026
Fabulous company and personal service.
We had a wonderful experience. The golf cart worked perfect perfectly. We’d love the locking trunk to leave things in as we shopped around. Customer service was wonderful highly recommend.
Read more
Jet Skis Key West
New York City
Key West Original Island Jet Ski Tour
Randy G, Aug 2026
Jet Skis Key West
Staff Ninni was awesome
Read more
Key west jet ski tour.
New York City
Key West Original Island Jet Ski Tour
William C, Aug 2026
Key west jet ski tour.
Awesome experience. By far the highlight of this trip.
Read more
Fabulous Wind & Wine Sunset Sail
New York City
Key West Wind & Wine Sunset Sail
Janet H, Jul 2026
Fabulous Wind & Wine Sunset Sail
We loved our sunset sail with Key West Wind and Wine By Cool Destinations. Everything was very organized. Captain Tony and his delightful crew were wonderful,friendly and very attentive. The choice of wines were great and varied . The passed nibbles were nicely curated. Highly recommend this as a perfect way to end the day in Key West. Nicely appointed and ideal for a relaxing evening. No loud music 👍👍and Not Crowded ❤️
Read more
Really Great 4-hour fishing trip
New York City
Premium Key West Party Head Boat Fishing Experience (Max 10 Guests)
Lou V, Jul 2026
Really Great 4-hour fishing trip
Captain Mike and Mate Luis made this fishing trip as enjoyable as one could expect. The party was friendly -- everyone had a good time. Cap gave a short historical tour of part of Key West harbor. The boat caught a good variety of fish: red grouper, lane snapper, yellowtail snapper, and white grunt. I enjoyed the music played as we fished -- mostly James Taylor, which added an island flavor to the island fishery.
Read more
Had a very enjoyable trip
New York City
Private Key West Deep Sea Fishing Charter
Barry M, Jul 2026
Had a very enjoyable trip
Unfortunately we didn't catch any fish. Capt Gary and mate Ed were extremely nice and knowledgeable
Read more
Great Charter
New York City
Key West Split Fishing Charter
Robert G, Jul 2026
Great Charter
Loved the fact although the recent fishing has not been good due to the seaweed bloom this year, Fish Key West was not fazed and we hit paydirt about 30 miles offshore with multiple catch (and awesome dinner). You got to love that beautiful Mahi Mahi biting! Great work skipper and Little Eddy. Nice to see a well oiled machine run by real fisherman. Loved it. Keep up the great work.
Read more
FUN DIVE
New York City
Key West PADI® Discover Scuba 1-day Resort Course
Ciera C, Jul 2026
FUN DIVE
Thorough training, friendly staff, awesome dive! Did not see a shark :( but still great
Read more
Key West Ultimate Adventure
New York City
Key West Original Full-Day Watersports Adventure
Colette G, Jul 2026
Key West Ultimate Adventure
Worth every penny!! My family of four had a blast! I have to admit, after seeing close to 70 people get on the catamaran I was a little concerned. Concern was not needed. The staff was so well organized it never felt like there was that many people there. We did the banana boat, jet skied, parasailed and played on the obstacle course. I felt like we had ample time at each experience. My two kids, 10(girl), 15(boy), had nothing but smiles the entire time. Snacks and drinks served hit the spot after all the sun and fun. Staff was so friendly, fun and on top of everything. We would 100% do this again!
Read more
Awesome fishing trip.
New York City
Private Key West Deep Sea Fishing Charter
Brent P, Jun 2026
Awesome fishing trip.
Professional and knowledgeable crew. Fun trip.
Read more
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