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Top Key West Luxury Tours

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

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

3 hours Free Cancellation
5.0 (5)
from
$500
Key West Christmas Cruise with Live Band and Drinks

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our …More

Likely to Sell Out
Likely to Sell Out

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our...

1 hour 30 minutes Free Cancellation
5.0 (5)
from
$98
Key West Ghost Tours: Southernmost Shadows and Ghosts

Explore the eerie streets of Key West with Southernmost Ghosts on a captivating hour-long walking tour that uncovers the city’s dark past. Led by passionate …More

Explore the eerie streets of Key West with Southernmost Ghosts on a captivating hour-long walking tour that uncovers the city’s dark past. Led by passionate...

1 hour Free Cancellation
4.6 (30)
from
$32
Hemingway Tour

You will begin this 65 minute nighttime guided walking tour by meeting your tour guide at Capt. Tony's Saloon outside front doors (428 Greene Street). …More

4.7 (13)

Hemingway Tour

You will begin this 65 minute nighttime guided walking tour by meeting your tour guide at Capt. Tony's Saloon outside front doors (428 Greene Street)....

1 hour 5 minutes Free Cancellation
4.7 (13)
from
$69
2-Hour Live Music Guided Tour in Key West

Discover Key West’s best live music with a local guide. Visit 4 music venues in two hours. The Ticket includes, drink discounts, digital guide for …More

Discover Key West’s best live music with a local guide. Visit 4 music venues in two hours. The Ticket includes, drink discounts, digital guide for...

2 hours Free Cancellation
5.0 (20)
from
$35
Dry Tortugas National Park Day Trip by Luxury Private Boat

Experience the Dry Tortugas in Unrivaled Luxury and Style aboard the Axopar 37 XC. This exclusive day trip offers the thrill of a high-performance luxury …More

Experience the Dry Tortugas in Unrivaled Luxury and Style aboard the Axopar 37 XC. This exclusive day trip offers the thrill of a high-performance luxury...

8 hours Free Cancellation
4.9 (10)
from
$250
Florida Keys Backcountry Eco Tour from Big Pine Key

This 2 hour Eco Tour will take you by boat to explore the Backcountry of the Florida Keys. We will cruise through the mangrove islands …More

This 2 hour Eco Tour will take you by boat to explore the Backcountry of the Florida Keys. We will cruise through the mangrove islands...

2 hours Free Cancellation
5.0 (35)
from
$399
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

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
$127
A Snorkel Tour with a Twist of History, Marathon, Florida Keys

Experience premier snorkeling in the Florida Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat …More

Experience premier snorkeling in the Florida Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat...

3 hours Free Cancellation
5.0 (1)
from
$70
Key West UFO Skywatch Tour with Night Vision

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else …More

Likely to Sell Out
Likely to Sell Out

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else...

1 hour 15 minutes Free Cancellation
5.0 (1)
from
$49
Summertime Morning Swim in the Florida Keys Catamaran

Start your day with a soothing adventure aboard Island Girls Excursions' 53-foot catamaran. The Summertime Morning Swim is a family-friendly experience designed to immerse you …More

Likely to Sell Out
Likely to Sell Out

Start your day with a soothing adventure aboard Island Girls Excursions' 53-foot catamaran. The Summertime Morning Swim is a family-friendly experience designed to immerse you...

3 hours Free Cancellation
5.0 (1)
from
$96
Sharkeys Glass Bottom Fish Feeding LED Night Tour Key West

The glass bottom kayaks is an amazing experience with your tour guides paddling in calm shallow waterways under the stars! Your tour guides will point …More

Likely to Sell Out
Likely to Sell Out

The glass bottom kayaks is an amazing experience with your tour guides paddling in calm shallow waterways under the stars! Your tour guides will point...

1 hour 15 minutes Free Cancellation
5.0 (1)
from
$62
Key West Historic Private Food Tour with 5 Authentic Tastings

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings …More

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings...

2 hours 30 minutes Free Cancellation
4.8 (19)
from
$145
Private Boat Tour of Flagler's Famous Bridges from Big Pine Key

This 1-hour boat ride/loop starts at the Spanish Harbor Bridge and goes up to the Bahia Honda Bridge and the Seven Mile Bridge. We’ll cruise …More

This 1-hour boat ride/loop starts at the Spanish Harbor Bridge and goes up to the Bahia Honda Bridge and the Seven Mile Bridge. We’ll cruise...

1 hour Free Cancellation
5.0 (19)
from
$325
Key West After Dark, Ghost, Santeria & Voodoo Pedicab Tour

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll …More

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll...

1 hour 30 minutes Free Cancellation
5.0 (7)
from
$158
Experience Florida Keys Boat Charter Private Tour

Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while …More

Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while...

1 hour 30 minutes Free Cancellation
5.0 (8)
from
$460
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

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 (13)
from
$599
Private Afternoon Snorkel with Sunset Sail in Key West

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon …More

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon...

4 hours Free Cancellation
5.0 (4)
from
$1,070
PRIVATE Guided Mangrove Eco-Tour Adventure

Paddle through the serene waters of Geiger Key at your own pace, with a private guided kayak/Paddleboard tour that immerses you in the natural beauty …More

Paddle through the serene waters of Geiger Key at your own pace, with a private guided kayak/Paddleboard tour that immerses you in the natural beauty...

2 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$395
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

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

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

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