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Key West Tours

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Key West Craft Cocktail Crawl

Join us on a sip and stroll through Key West's craftiest bars and hidden local gems enjoying 5 local cocktails & 2 food tastings! Discover the …More

4.9 (614)

Key West Craft Cocktail Crawl

Join us on a sip and stroll through Key West's craftiest bars and hidden local gems enjoying 5 local cocktails & 2 food tastings! Discover the...

3 hours • Free Cancellation
4.9 (614)
from
$99
Southernmost Food & Cultural Walking Tour by Key West Food Tours

Enjoy a taste of Key West on this 3-hour food walking tour, led by an expert guide. Along the way visit 5 locally-run “mom and pop” establishments in …More

4.9 (1,938)

Southernmost Food & Cultural Walking Tour by Key West Food Tours

Enjoy a taste of Key West on this 3-hour food walking tour, led by an expert guide. Along the way visit 5 locally-run “mom and pop” establishments in...

3 hours • Free Cancellation
4.9 (1,938)
from
$94
All-Inclusive Sandbar Safari with Dolphin Playground Encounter

Embark on a journey like no other. This tour takes guests on an amazing journey from Key West to a secluded sandbar & then to …More

4.9 (665)

All-Inclusive Sandbar Safari with Dolphin Playground Encounter

Embark on a journey like no other. This tour takes guests on an amazing journey from Key West to a secluded sandbar & then to...

5 hours • Free Cancellation
4.9 (665)
from
$150
Key West Historic Seaport Food & Walking Tour

Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West. Savor maritime history through delicious seafood (or tasty non-seafood …More

4.9 (681)

Key West Historic Seaport Food & Walking Tour

Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West. Savor maritime history through delicious seafood (or tasty non-seafood...

3 hours • Free Cancellation
4.9 (681)
from
$94
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 (422)

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 (422)
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
Adult Only Sandbar Escape with Drinks in Key West

One of the only Adult Only experiences offered in Key West, our excursions are top-notch, with the vessel, all equipment, food and beverage service being …More

4.8 (40)

Adult Only Sandbar Escape with Drinks in Key West

One of the only Adult Only experiences offered in Key West, our excursions are top-notch, with the vessel, all equipment, food and beverage service being...

4 hours • Free Cancellation
4.8 (40)
from
$129
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
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 (41)

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 (41)
from
$137
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
Key West Dolphin Tour & Snorkeling- Small Group

Featured in National Geographic Travel - Over 2000 five-star reviews and ranked #1 on Google Maps for Key West dolphin tours. Small Groups, Big Experience …More

4.9 (119)

Key West Dolphin Tour & Snorkeling- Small Group

Featured in National Geographic Travel - Over 2000 five-star reviews and ranked #1 on Google Maps for Key West dolphin tours. Small Groups, Big Experience...

3 hours • Free Cancellation
4.9 (119)
from
$128
The Hemingway Experience in Key West

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour …More

4.9 (68)

The Hemingway Experience in Key West

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour...

4 hours • Free Cancellation
4.9 (68)
from
$189
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
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
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
Key West Wreckers Race Aboard Schooner America 2.0

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in …More

4.9 (14)

Key West Wreckers Race Aboard Schooner America 2.0

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in...

3 hours
4.9 (14)
from
$116
Island Sandbar Tour Catamaran Cruise in Marathon FL

Experience a classic Florida Keys sandbar adventure on a comfortable 53’ catamaran. Cruise through Boot Key Harbor and past scenic landmarks as your crew shares …More

5.0 (9)

Island Sandbar Tour Catamaran Cruise in Marathon FL

Experience a classic Florida Keys sandbar adventure on a comfortable 53’ catamaran. Cruise through Boot Key Harbor and past scenic landmarks as your crew shares...

4 hours • Free Cancellation
5.0 (9)
from
$130
Key West Hidden Sanctuary Mangrove Kayak Tour With Drinks

Key West’s Most Secluded Kayak & Sandbar Adventure Escape the crowds and explore Key West’s most secluded kayak tour in the Florida Marine Sanctuary. Unlike …More

4.6 (9)

Key West Hidden Sanctuary Mangrove Kayak Tour With Drinks

Key West’s Most Secluded Kayak & Sandbar Adventure Escape the crowds and explore Key West’s most secluded kayak tour in the Florida Marine Sanctuary. Unlike...

5 hours • Free Cancellation
4.6 (9)
from
$161

Frequently Asked Questions

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

Recent tour reviews
Amazing Craft Cocktail Crawl
New York City
Key West Craft Cocktail Crawl
jo4razorbacks, Sep 2026
Amazing Craft Cocktail Crawl
We booked two different tours during our Key West trip& were lucky enough to have Zona as our guide for both! The cocktail crawl was such a fun way to get off the beaten path & discover some of the local bars we never would have found on our own. The cocktails were delicious & unique, the bites were great & Zona’s stories & knowledge of Key West made every stop even more interesting. The flaming Zombie was the perfect finale! The tour was another fantastic experience with Zona & definitely a highlight of our trip. We highly recommend.
Read more
Key West Southernmost Food Tour
New York City
Southernmost Food & Cultural Walking Tour by Key West Food Tours
jo4razorbacks, Sep 2026
Key West Southernmost Food Tour
We had such a great time exploring the “real” Key West with Zona! She was fun & incredibly knowledgeable, sharing stories & history along the way that made the experience so much more than just a food tour. We loved getting off the beaten path & discovering local spots we probably never would have found on our own. The food & drinks were delicious & we left very full! This tour was a fun, memorable afternoon & a wonderful way to experience another side of Key West. We highly recommend Zona & this tour!
Read more
Walk, eat and learn
New York City
Southernmost Food & Cultural Walking Tour by Key West Food Tours
Htlgolf, Sep 2026
Walk, eat and learn
Lots of history, great food and a friendly guide
Read more
Bar tour 9/28
New York City
Key West Craft Cocktail Crawl
Maryann_M, Sep 2026
Bar tour 9/28
Such a relaxed fun experience. Learned about the history of some local bars. Especially loved the “off the beaten path”ones. The drinks were delicious, had options- esp if you have allergies. Rose, our guide was absolutely delightful. He was fun, personable, so knowledgeable, he totally made the tour a delight. Highly recommend.
Read more
Visitors from the Natti
New York City
All-Inclusive Sandbar Safari with Dolphin Playground Encounter
Timothy_P, Sep 2026
Visitors from the Natti
This was a very fun experience. Kayla, Kelsey and Madison were fantastic hosts. They were all very knowledgeable about the environment as well as the watercraft. We had a very fun and relaxing experience and saw many many dolphin. Absolutely recommend.
Read more
Sand bar cruise
New York City
All-Inclusive Sandbar Safari with Dolphin Playground Encounter
Amna_R, Sep 2026
Sand bar cruise
This excursion was the best! So much fun seeing the dolphins and hanging out on the sand bar The crew Claire and Bracken were great definitely gonna do this excursion again
Read more
This trip made my vacation complete!!!!
New York City
Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks
dorothyb638, Sep 2026
This trip made my vacation complete!!!!
I forgot the day we were going so we missed our sailing. Just going to say that this company went above and beyond and squeezed us in 2 days later. We went with Logan, Abby and Nic and they were wonderful! Not sure how Logan did it but we left the dock with light rain and dark clouds, yet he found us sun and light blue water over the most beautiful sandbar I’ve ever seen! We had plenty to eat, the best “special” mimosas and so much fun. The price was worth everything the trip offered. If you are thinking of going, do it! Even my husband who dislikes beaches enjoyed himself.
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
Amazing Food Tour and Guide 😋
New York City
Key West Historic Seaport Food & Walking Tour
Neil_P, Sep 2026
Amazing Food Tour and Guide 😋
GoGo was an amazing tour guide. We have been to Key West many times but he showed us so many things and places we had never been to before. We even enjoyed going to some of our favorite places here with him, he shared information we were not aware of. All the stops were great and his knowledge of Key West was impressive. We highly recommend this tour to anyone visiting Key West. Everything was delicious!! Only complaint is how full we are and how will we ever be able to eat dinner!!!!! Thank you for an awesome day.
Read more
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
We thought this was a...
New York City
Adult Only Sandbar Escape with Drinks in Key West
Jennifer_D, Sep 2026
We thought this was a...
We thought this was a great trip! Zack and Tommy were very personable, attentive, and just all around fun guys to lead this tour. We were a little lucky that only a few other couples were on this trip so it was a very relaxing and easy going time. Sand bar area was amazing.
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
Happy customer
New York City
Adult Only Sandbar Escape with Drinks in Key West
Shanitra_M, Sep 2026
Happy customer
Great day! Al & Thomas were great captains. Enjoyed the champagne, snacks and sandwich. And it was a good amount of time spent in water. Would definitely do again.
Read more
Walking history and food tour was perfect!
New York City
The Hemingway Experience in Key West
Mobile64216837234, Sep 2026
Walking history and food tour was perfect!
Excellent tour! History, fun facts, cultural influences. Great food and beverages. Jo was an excellent tour guide - enthusiastic and knowledgeable of Key West, Hemingway, local lore and just a fun guide. Highly recommend this tour.
Read more
Highly recommend
New York City
The Hemingway Experience in Key West
Justin_C, Sep 2026
Highly recommend
AmyJo was an amazing guide. Fun and extremely knowledgeable. The tour was packed with information and delicious food and drinks, all at a very leisurely pace.
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
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