Top Key West Luxury Tours

Q: What are the best options for Key West Luxury Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Key West Luxury Tours are: Key West Dolphin Tour & Snorkeling- Small Group Key Lime Pie Walking Tour of Key West Historic Seaport Schooner Appledore Day Sail with Full Bar in Key West Key West Sandbar Adventure Cruise for All Ages Key West Clear Kayak Eco Tour

Q: What are the best kid-friendly options for Key West Luxury Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Key West Luxury Tours are: Ghosts of Key West: Haunted History Walking Tour Key West Ghost Tours: Southernmost Shadows and Ghosts Key West Ghost and Mysteries Guided Tour Tropical Fruit Hunting Tour at Grimal Grove Key West Ghosts and Gravestones Trolley Tour View all kid-friendly Tours →

Q: Which Key West Luxury Tours have Instant Confirmation?

Key West Luxury Tours with Instant Confirmation include: Key West Pirate Adventure: Self-Guided Walking Tour Hemingway's Key West Self Guided outdoor Walking Audio Tour Florida Key West Self-Guided Walking Audio Tour Key West Smartphone guided Ghost Walking Tour App/GPS/EMF Reader Key West History Audio Guided Walking Tour 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 →

Enjoy a Spectacular Key West Sunset Cruise Looking for the perfect way to end your day? Join us on the Seabreeze, your 42-foot Corinthian powercat, …More

5.0 (1)

Key West Sushi and Sunset Cruise

Enjoy a Spectacular Key West Sunset Cruise Looking for the perfect way to end your day? Join us on the Seabreeze, your 42-foot Corinthian powercat,...

2 hours Free Cancellation

5.0 (1)

from
$91

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar. …More

4.4 (1,934)

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar....

2 hours Free Cancellation

4.4 (1,934)

from
$93

Key West Attractions Pass with Trolley Tour

Explore the vibrant sights of Key West with the Old Town Trolley, Aquarium, and Shipwreck Museum package. This tour offers unlimited hop-on, hop-off access to …More

3.0 (1)

Key West Attractions Pass with Trolley Tour

Explore the vibrant sights of Key West with the Old Town Trolley, Aquarium, and Shipwreck Museum package. This tour offers unlimited hop-on, hop-off access to...

1 hour 30 minutes Free Cancellation

3.0 (1)

from
$93

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 (1,979)

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 (1,979)

from
$94

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 (682)

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 (682)

from
$94

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

5.0 (1)

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...

3 hours Free Cancellation

5.0 (1)

from
$96

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

5.0 (5)

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...

1 hour 30 minutes Free Cancellation

5.0 (5)

from
$98

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 (621)

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 (621)

from
$99

Shark and Wildlife Viewing Adventure in Key West

This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to …More

5.0 (3,312)

Shark and Wildlife Viewing Adventure in Key West

This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to...

2 hours Free Cancellation

5.0 (3,312)

from
$99

Key West: Robert the Doll After Dark VIP Ghost Hunt (2 Hours)

Go where other tours can’t. Enter historic Fort East Martello after dark, meet Robert the Doll, then stay behind for an extended paranormal investigation inside …More

4.7 (169)

Key West: Robert the Doll After Dark VIP Ghost Hunt (2 Hours)

Go where other tours can’t. Enter historic Fort East Martello after dark, meet Robert the Doll, then stay behind for an extended paranormal investigation inside...

2 hours Free Cancellation

4.7 (169)

from
$99

Key West Sunset Sail Aboard Legendary Schooner Appledore

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 (369)

Key West Sunset Sail Aboard Legendary Schooner Appledore

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 (369)

from
$99

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

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

Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West

Depart the island of Key West & enjoy a full day of sightseeing along the iconic Overseas Highway! You'll travel halfway up the keys to …More

4.9 (37)

Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West

Depart the island of Key West & enjoy a full day of sightseeing along the iconic Overseas Highway! You'll travel halfway up the keys to...

7 hours Hotel pickup offered Free Cancellation

4.9 (37)

from
$100

Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida

Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks …More

5.0 (22)

Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida

Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks...

2 hours Free Cancellation

5.0 (22)

from
$102

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

4.9 (16)

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 (16)

from
$102

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's …More

5.0 (292)

Sunset Sail Cruise in Key West

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...

2 hours Free Cancellation

5.0 (292)

from
$102

Key West Historic Old Town 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

4.8 (312)

Key West Historic Old Town 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...

2 hours 30 minutes Free Cancellation

4.8 (312)

from
$108

Classic Key West Schooner Sunset Sail with Full Open Bar

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This …More

4.9 (283)

Classic Key West Schooner Sunset Sail with Full Open Bar

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This...

2 hours Free Cancellation

4.9 (283)

from
$109

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 (119)

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 (119)

from
$119