Top Key West Luxury Tours

Q: Which Key West Luxury Tours have Instant Confirmation?

Key West Luxury Tours with Instant Confirmation include: Shark and Wildlife Viewing Adventure in Key West Guided Bike Tour of Old Town Key West Key West Mangrove Kayak Eco Tour Southernmost Food & Cultural Walking Tour by Key West Food Tours Key West Private Wind & Wine Charter View all Tours with Instant Confirmation →

Q: I need a ride! Which Key West Luxury Tours have Hotel Pickup?

No problem. These Key West Luxury Tours include Hotel Pickup: Florida Keys Nature & History Tour from Key West Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West PRIVATE Guided Mangrove Eco-Tour Adventure View all Tours with Hotel Pickup →

Q: Got any more Key West trip ideas?

We sure do. Check out our curated lists of hand-picked Key West Tours. Top 10 Key West 2026 Senior-friendly tours Key West The best tours and activities for culture lovers in Key West Top Day Trips from Key West Things to do in Key West this summer View all Key West Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Key West?

Based on our sales data over the past year, the most popular styles of tours and activities in Key West are: Key West Kid Friendly Key West Kid Friendly Tours & Activities Key West Vehicle Rentals Key West Golf Cart Rentals Key West Water Sports View all tour styles in Key West →

Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you …More

4.8 (188)

Key West Mini Catamaran Eco Tour

Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you...

1 hour 30 minutes Free Cancellation

4.8 (188)

from
$285

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

4.9 (182)

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...

2 hours

4.9 (182)

from
$65

Southernmost Key West History and Culture Small-Group Walking Tour

Meet The Locals, On Foot, At Eye Level If you’re like us, you think of travel as more than just “going places.” You crave experience …More

5.0 (135)

Southernmost Key West History and Culture Small-Group Walking Tour

Meet The Locals, On Foot, At Eye Level If you’re like us, you think of travel as more than just “going places.” You crave experience...

1 hour 45 minutes Free Cancellation

5.0 (135)

from
$54

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 (120)

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 (120)

from
$149

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 (118)

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 (118)

from
$119

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

Schooner Appledore Day Sail with Full Bar in Key West

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern …More

5.0 (113)

Schooner Appledore Day Sail with Full Bar in Key West

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

2 hours Free Cancellation

5.0 (113)

from
$54

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

4.8 (109)

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,...

2 hours Free Cancellation

4.8 (109)

from
$99

Dinghy Drinking Tour through Key West Waters

On this tour, you will see the beautiful crystal clear waters around Key West from a dinghy, a small motor boat that seats up to …More

4.9 (108)

Dinghy Drinking Tour through Key West Waters

On this tour, you will see the beautiful crystal clear waters around Key West from a dinghy, a small motor boat that seats up to...

3 hours Free Cancellation

4.9 (108)

from
$85

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 (98)

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 (98)

from
$20

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 (73)

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 (73)

from
$189

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
$158

Cruisin Tikis Marathon - Sunset Tiki Cruise

Ready for the most beautiful 2 hours of your Florida Keys vacation? Forget crowded piers and noise—imagine yourself drifting peacefully as the sun melts into …More

5.0 (68)

Cruisin Tikis Marathon - Sunset Tiki Cruise

Ready for the most beautiful 2 hours of your Florida Keys vacation? Forget crowded piers and noise—imagine yourself drifting peacefully as the sun melts into...

2 hours Free Cancellation

5.0 (68)

from
$99

*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

4.9 (66)

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 (66)

from
$400

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

4.9 (62)

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,...

1 hour 30 minutes Free Cancellation

4.9 (62)

from
$70

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 (54)

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 (54)

from
$500

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

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
$693

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 (48)

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 (48)

from
$137