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Top Key West Private Sightseeing Tours

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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
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
Florida Key West Self-Guided Walking Audio Tour

Explore beautiful coastlines, wild history, and fascinating wildlife with this self-guided walking tour of Key West. Get to know famed author Ernest Hemingway and the …More

4.7 (26)

Florida Key West Self-Guided Walking Audio Tour

Explore beautiful coastlines, wild history, and fascinating wildlife with this self-guided walking tour of Key West. Get to know famed author Ernest Hemingway and the...

2 to 3 hours • Free Cancellation
4.7 (26)
from
$10
Self-Guided Driving Audio Tour in Florida Keys

Don't miss a thing as the GuideAlong Audio Driving Tour takes you on an incredible self-guided journey on one of the most classic US road …More

4.8 (97)

Self-Guided Driving Audio Tour in Florida Keys

Don't miss a thing as the GuideAlong Audio Driving Tour takes you on an incredible self-guided journey on one of the most classic US road...

1 day • Free Cancellation
4.8 (97)
from
$17
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
Private Looe Key Snorkel from Big Pine Key

Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef …More

5.0 (444)

Private Looe Key Snorkel from Big Pine Key

Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef...

3 hours • Free Cancellation
5.0 (444)
from
$569
Private Sunset Cruise around Key West

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour around the island of Key West on our 20 foot pioneer center console. Your …More

Likely to Sell Out
Likely to Sell Out
4.9 (65)

Private Sunset Cruise around Key West

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour around the island of Key West on our 20 foot pioneer center console. Your...

2 hours • Free Cancellation
4.9 (65)
from
$400
Key West Smartphone guided Ghost Walking Tour App/GPS/EMF Reader

Go at your own pace and schedule. You'll see Key West's most haunted spots and hear their ghostly stories on spooky solo walking tour on …More

4.7 (7)

Key West Smartphone guided Ghost Walking Tour App/GPS/EMF Reader

Go at your own pace and schedule. You'll see Key West's most haunted spots and hear their ghostly stories on spooky solo walking tour on...

40 to 55 minutes • Free Cancellation
4.7 (7)
from
$10
Key West Conch Republic Tiki Pedicab Experience by Kokomo Cabs

You will sit and relax on our spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting …More

5.0 (69)

Key West Conch Republic Tiki Pedicab Experience by Kokomo Cabs

You will sit and relax on our spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting...

2 hours 30 minutes • Free Cancellation
5.0 (69)
from
$229
Hemingway's Key West Self Guided outdoor Walking Audio Tour

Want to discover Hemingway's story in Key West? This tour is outside (no tickets to the Hemingway house) See the many sites he's linked to? …More

4.3 (3)

Hemingway's Key West Self Guided outdoor Walking Audio Tour

Want to discover Hemingway's story in Key West? This tour is outside (no tickets to the Hemingway house) See the many sites he's linked to?...

60 to 90 minutes • Free Cancellation
4.3 (3)
from
$8
Boat Excursion in Florida Keys with Snorkeling Equipment

Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the …More

5.0 (22)

Boat Excursion in Florida Keys with Snorkeling Equipment

Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the...

4 hours • Free Cancellation
5.0 (22)
from
$700
Private Sandbar Adventure in Key West Backcountry

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle …More

5.0 (51)

Private Sandbar Adventure in Key West Backcountry

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle...

3 hours • Free Cancellation
5.0 (51)
from
$500
Marathon to Key West Private Tour of Florida Keys

Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS • …More

5.0 (28)

Marathon to Key West Private Tour of Florida Keys

Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS •...

8 hours • Free Cancellation
5.0 (28)
from
$84
Private Key West Sunset Sail

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for …More

Likely to Sell Out
Likely to Sell Out
4.9 (50)

Private Key West Sunset Sail

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for...

2 hours
4.9 (50)
from
$695
PRIVATE Welcome to Key West Walking Tour

Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during …More

Likely to Sell Out
Likely to Sell Out
4.9 (22)

PRIVATE Welcome to Key West Walking Tour

Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during...

90 to 180 minutes • Free Cancellation
4.9 (22)
from
$55
Key West’s Old Town Treasures: A Self-Guided Audio Tour

See Key West’s top attractions from the Lighthouse to the Little White House at your own pace with this affordable walking tour. • Find out …More

4.3 (30)

Key West’s Old Town Treasures: A Self-Guided Audio Tour

See Key West’s top attractions from the Lighthouse to the Little White House at your own pace with this affordable walking tour. • Find out...

90 to 120 minutes • Free Cancellation
4.3 (30)
from
$15
Private 90-Minute Harbor Sailing Charter in Key West

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida …More

4.9 (19)

Private 90-Minute Harbor Sailing Charter in Key West

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida...

1 hour 30 minutes • Free Cancellation
4.9 (19)
from
$425
Key West Boat Experience — Swim, Sip & Soak Up the Sun!

Welcome to Key West Boat & Jet Ski Adventures! Explore Key West's Backcountry Aboard Our Brand-New Manitou Cruise with Swim Deck Set out on a …More

Likely to Sell Out
Likely to Sell Out
4.9 (9)

Key West Boat Experience — Swim, Sip & Soak Up the Sun!

Welcome to Key West Boat & Jet Ski Adventures! Explore Key West's Backcountry Aboard Our Brand-New Manitou Cruise with Swim Deck Set out on a...

4 hours • Free Cancellation
4.9 (9)
from
$600
Escape Rooms Outdoors on the Waters of Key West!

Choose your adventure! Castaway, Mermaid, or Conch Quest !! Each charter is four (4) hours, with the escape game being one hour of the adventure …More

Likely to Sell Out
Likely to Sell Out
5.0 (5)

Escape Rooms Outdoors on the Waters of Key West!

Choose your adventure! Castaway, Mermaid, or Conch Quest !! Each charter is four (4) hours, with the escape game being one hour of the adventure...

4 hours • Free Cancellation
5.0 (5)
from
$500
The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the …More

Likely to Sell Out
Likely to Sell Out
5.0 (9)

The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the...

2 hours • Free Cancellation
5.0 (9)
from
$599

Frequently Asked Questions

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

Recent tour reviews
Great Snorkel Trip with Keys Boat Tours
New York City
Private Looe Key Snorkel from Big Pine Key
adamlJ3958WX, Sep 2026
Great Snorkel Trip with Keys Boat Tours
We originally booked a Looe Key reef snorkel, but the wind was too strong. Keys Boat Tours called with an option to go to the bay side and snorkle along the mangrove islands. We decided to go with that and adjusted the time to hit the slack tide.Capt Brian was excellent. We rode out from Big Pine under the bridges and out to one of the bay islands. There were 5 of us. Three of us snorkled all along the mangrove island and were able to see many kinds of fish, barracuda and even a couple of small sharks. Two stayed close to the boat and snorkled with a noodle. Whatever your skill or swimming level, there's a way to enjoy the experience.Capt Brian was great, knowing where to go and knowledgeable about the area. If you are looking for a private snorkel trip, I would highly recommend Keys Boat Tours. And also check out Capt Brian's guide book, The Road to Key West. It's packed full of information about the Lower Keys.
Read more
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
Scott made this night amazing!
New York City
The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise
E373DFannaw, Sep 2026
Scott made this night amazing!
Scott was amazing!!! Fun and he knew so much about the area! Such a great sunset cruise. When we’re back in the area we will definitely request Scott again!
Read more
Definately worth it
New York City
Self-Guided Driving Audio Tour in Florida Keys
maryjoh813, Aug 2026
Definately worth it
The self guide tour was very informative. It provided good commentary and information along the route and possible place to stop or visit. We used the tour from Key West to Key Largo and back and the in downtown Key Largo for information regarding places to see in Key West and their exact location. I was not sure if a self-guided tour would be that good but i was surprised by it's accuracy and narration. I would definitely recommend this tour and would consider purchasing other tours in the future.
Read more
Amazing
New York City
The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise
Trek11715299746, Aug 2026
Amazing
Captain Ross was absolutely amazing, we had fun, good conversations and the best sunset view ,docked.
Read more
Dom was excellent!...
New York City
Private Sandbar Adventure in Key West Backcountry
Corey_E, Aug 2026
Dom was excellent!...
Dom was excellent! Definitely recommend! Very affordable private sandbar charter. Would do it again for sure.
Read more
You DEFINITELY want to book this
New York City
Private Looe Key Snorkel from Big Pine Key
Seaside18310458770, Jul 2026
You DEFINITELY want to book this
My family and I went out with Captain Brian to snorkel at Looe Key and we had the most incredible time. It was a 4 hour excursion and there were 5 of us in the group. Every minute was filled with immense excitement and joy. Captain Brian himself is one of the coolest people we’ve ever met. He was so laid back, kind, and knowledgeable. The views at Looe Key were literally jaw dropping. It felt like we were inside of a big aquarium tank with the diversity of fish, corals, and colors we saw! We were lucky enough to see a nurse shark, a juvenile bull shark, hundreds of fish, a moray eel, a sting ray, conchs, etc.. It is a very happy and healthy coral reef and I still can’t believe I got to experience it first hand. I know there are other companies you could choose from to go to Looe Key, but none of them compare to Captain Brian. He even took the time to fog proof every pair of goggles so that we could have the best visibility the whole time. If you’re looking for amazing vibes, an experience you’ll talk about for the rest of your life, and a captain who’s whole goal is to ensure you have the most fantastic time, then you’ve got to book with Captain Brian.
Read more
Escape room but on the water!
New York City
Escape Rooms Outdoors on the Waters of Key West!
Seaside819162, Jul 2026
Escape room but on the water!
We had an amazing time on the escape island boat excursion in Key West! The ride out to the island was beautiful with incredible views. Captain Kyle had an escape Gilligan's island with clues planted on the island. We had 1 hour to escape Gilligan's island. This was definitely one of the highlights of your trip to Key West. I highly recommend this excursion to anyone looking for a fun and memorable day on the water!
Read more
The best way to explore Key West
New York City
Key West Conch Republic Tiki Pedicab Experience by Kokomo Cabs
james_g, Jul 2026
The best way to explore Key West
My wife and I had such an amazing time checking out all the cool sites! AJ totally explained everything to us, telling us what everything was and all the history behind it. It was seriously just so awesome!
Read more
Multiple Bookings, Amazing Experiences
New York City
Private Sandbar Adventure in Key West Backcountry
Alec S, Jul 2026
Multiple Bookings, Amazing Experiences
I’ve booked Cpt Donnie 5 times now I think…he is an amazing charter captain. Hardworking, easy going, fun etc. he makes you feel welcome. Everytime my family comes down, we book him. You cannot go wrong. He knows the best spots and will give you the saltwater experience you’re looking for…whether it’s sunset or sandbar. Highly recommend!
Read more
Great purchase
New York City
Self-Guided Driving Audio Tour in Florida Keys
K3696VRjackiek, Jul 2026
Great purchase
I've never purchased an audio tour before, but it was money well spent. It took a few minutes to get set-up (not very tech-savvy), but we figured it out. The narrator was entertaining and we were impressed the landmarks for directions were still in place. It made the long drive very entertaining and we learned a lot about the history of the area, sites, and restaurants. (Sunset Grill by the 7-mile bridge was great and breath-taking views)
Read more
Marathon to Key West
New York City
Marathon to Key West Private Tour of Florida Keys
Carmen_H, Jun 2026
Marathon to Key West
Our driver Troy was fantastic! We all had a great time seeing all the sites in and around Key West. I would definitely recommend this for a group of friends.
Read more
Easy to use, simple but interesting facts
New York City
Key West’s Old Town Treasures: A Self-Guided Audio Tour
Pamela_R, Jun 2026
Easy to use, simple but interesting facts
The app, then the tour are easy to download and easy to use. Certainly worth the money. The GPS feature works. I only wish you could take the tour in different order.
Read more
Road trip from Miami to Key West
New York City
Florida Key West Self-Guided Driving Tour (7 Mile Bridge)
meredith685, Jun 2026
Road trip from Miami to Key West
Very educational. Probably would not have known about some the history of the sites without the self guided tour
Read more
An Unforgettable Experience
New York City
Hemingway’s Key West Self Guided outdoor Walking Audio Tour
Madeline_M, Jun 2026
An Unforgettable Experience
A beautiful place to tour. Alot of History. Although he died at 62, he lived a full life and it showed. Rob was an AMAZING TOUR GUIDE, FULL OOF KNOWLEDGE AND FUNNY TO BOOT.
Read more
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