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 Cocktail Cruise Adults Only Sunset Cruise with Open Bar Florida Keys Nature & History Tour from Key West Southernmost Key West History and Culture Small-Group Walking Tour The Hemingway Experience in Key West Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

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 →

History Nature and Culture of Key West Walking Tour

This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local …More

5.0 (4)

History Nature and Culture of Key West Walking Tour

This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local...

1 hour 30 minutes Free Cancellation

5.0 (4)

from
$69

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

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

Key West Sweet Treats Food Tour: Sunshine & Sweet Times

Discover the sweeter side of paradise on the Key West Sweets Tour! This fun and flavorful walking tour takes you through the heart of Old …More

4.7 (23)

Key West Sweet Treats Food Tour: Sunshine & Sweet Times

Discover the sweeter side of paradise on the Key West Sweets Tour! This fun and flavorful walking tour takes you through the heart of Old...

2 hours Free Cancellation

4.7 (23)

from
$70

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

5.0 (1)

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...

3 hours Free Cancellation

5.0 (1)

from
$70

Sunset Sail in Key West with Beverages Included

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention …More

4.9 (982)

Sunset Sail in Key West with Beverages Included

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...

1 hour 30 minutes Free Cancellation

4.9 (982)

from
$79

You will begin this 1 hour and 30 minute guided tour by meeting your tour guide, (who will be wearing a neon green shirt) at …More

4.8 (321)

Jimmy Buffett Tour

You will begin this 1 hour and 30 minute guided tour by meeting your tour guide, (who will be wearing a neon green shirt) at...

1 hour 30 minutes Free Cancellation

4.8 (321)

from
$79

Explore the vibrant history of Key West on this engaging bike tour. Pedal through charming streets as you uncover the stories behind the island's notable …More

5.0 (1)

Historic Key West Bike Tour

Explore the vibrant history of Key West on this engaging bike tour. Pedal through charming streets as you uncover the stories behind the island's notable...

2 hours Free Cancellation

5.0 (1)

from
$79

Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key …More

4.9 (2,389)

Key West Mangrove Kayak Eco Tour

Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key...

2 hours Free Cancellation

4.9 (2,389)

from
$80

Key West Day Sail on Schooner America 2.0 with 2 Drinks

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that …More

5.0 (213)

Key West Day Sail on Schooner America 2.0 with 2 Drinks

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that...

1 hour 30 minutes Free Cancellation

5.0 (213)

from
$82

Marathon to Key West Private Tour of Florida Keys

Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS • …More

5.0 (29)

Marathon to Key West Private Tour of Florida Keys

Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS •...

8 hours Free Cancellation

5.0 (29)

from
$84

Embark on a lively 1.5-hour Tiki Fun Cruise through the stunning Florida Keys. Glide over crystal-clear waters on an authentic tiki bar boat, where you …More

5.0 (34)

Florida Keys Tiki Boat Tour Adventure

Embark on a lively 1.5-hour Tiki Fun Cruise through the stunning Florida Keys. Glide over crystal-clear waters on an authentic tiki bar boat, where you...

2 hours Free Cancellation

5.0 (34)

from
$85

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

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

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

5.0 (33)

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...

2 hours Free Cancellation

5.0 (33)

from
$85

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

5.0 (5)

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...

1 hour 45 minutes Free Cancellation

5.0 (5)

from
$89

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or …More

5.0 (10)

Key West Nighttime Full Moon Sail

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or...

1 hour 30 minutes Free Cancellation

5.0 (10)

from
$89

Guided Clear Kayak Eco-Tour Near Key West

100% Clear Kayaks: Unlike traditional kayaks, ours are completely see-through. As you paddle, you'll have a front-row seat to the vibrant marine life beneath the …More

4.9 (738)

Guided Clear Kayak Eco-Tour Near Key West

100% Clear Kayaks: Unlike traditional kayaks, ours are completely see-through. As you paddle, you'll have a front-row seat to the vibrant marine life beneath the...

2 hours Free Cancellation

4.9 (738)

from
$89

Morning Mimosa and Swim 2hr Luxury Cruise in Marathon FL

Experience a relaxing start to your day on a spacious 53’ luxury catamaran as you cruise through the clear waters surrounding Marathon. Enjoy a complimentary …More

5.0 (3)

Morning Mimosa and Swim 2hr Luxury Cruise in Marathon FL

Experience a relaxing start to your day on a spacious 53’ luxury catamaran as you cruise through the clear waters surrounding Marathon. Enjoy a complimentary...

2 hours Free Cancellation

5.0 (3)

from
$89