Key West Luxury Tours

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

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 (73)
from
$189
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

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 (118)
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

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 (42)
from
$150
Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

“The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West pleasure …More

“The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West pleasure...

2 hours
4.9 (182)
from
$65
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

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
$8
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

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 (98)
from
$20
Florida Keys Sunset Cruise with Champagne Toast and Seafood

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Sparky’s Landing in Marathon, this relaxing cruise includes a complimentary champagne toast and …More

Likely to Sell Out
Likely to Sell Out

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Sparky’s Landing in Marathon, this relaxing cruise includes a complimentary champagne toast and...

2 hours Free Cancellation
5.0 (33)
from
$85
iWitness Key West True Crime Walking Tour

True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and …More

True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and...

1 hour 30 minutes Free Cancellation
4.8 (19)
from
$49
Key West: Robert the Doll After Dark Ghost Tour (1 Hour)

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most …More

Likely to Sell Out
Likely to Sell Out

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most...

1 hour Free Cancellation
4.9 (7)
from
$45
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

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

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 (446)
from
$569
Key West Shore Excursion: Conch Tour Train

Ride the World Famous Conch Tour Train, the charming and whimsical Key West attraction that has been delighting locals and visitors alike since 1958. …More

Ride the World Famous Conch Tour Train, the charming and whimsical Key West attraction that has been delighting locals and visitors alike since 1958....

1 hour 30 minutes Free Cancellation
4.6 (42)
from
$45
Key West Night Cruise aboard Schooner America 2.0

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy …More

Likely to Sell Out
Likely to Sell Out

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy...

1 hour 45 minutes Free Cancellation
5.0 (5)
from
$89
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

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
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

*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 (66)
from
$400
Hemingway Food and Walking Tour

This guided walking tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches, …More

Likely to Sell Out
Likely to Sell Out

This guided walking tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches,...

2 hours Free Cancellation
4.8 (109)
from
$99
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

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
Ghosts of Key West: Haunted History Walking Tour

Discover a darker side of Key West on a 90-minute walking ghost tour through the historic streets of Old Town. Led by an engaging Ghost …More

Discover a darker side of Key West on a 90-minute walking ghost tour through the historic streets of Old Town. Led by an engaging Ghost...

1 hour 30 minutes Free Cancellation
4.6 (130)
from
$30
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

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 (120)
from
$149
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

*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 (54)
from
$500
Key Lime Pie Walking Tour of Key West Historic Seaport

Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie, …More

Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie,...

1 hour 30 minutes Free Cancellation
4.9 (62)
from
$70

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