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 →

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

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

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

Key West Sandbar Adventure Cruise for All Ages

Wake up and start your day in paradise the right way! We will give you an experience not easily forgotten, starting with a cruise through …More

4.9 (28)

Key West Sandbar Adventure Cruise for All Ages

Wake up and start your day in paradise the right way! We will give you an experience not easily forgotten, starting with a cruise through...

4 hours Free Cancellation

4.9 (28)

from
$126

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

Boat Excursion in Florida Keys with Snorkeling Equipment

Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the …More

5.0 (22)

Boat Excursion in Florida Keys with Snorkeling Equipment

Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the...

4 hours Free Cancellation

5.0 (22)

from
$700

PRIVATE Welcome to Key West Walking Tour

Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during …More

4.9 (22)

PRIVATE Welcome to Key West Walking Tour

Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during...

90 to 180 minutes Free Cancellation

4.9 (22)

from
$55

Tropical Fruit Hunting Tour at Grimal Grove

Visit the only Breadfruit Grove in Continental United States! While here, discover the rich history of Grimal Grove and its legendary founder, Adolf Grimal, on …More

5.0 (21)

Tropical Fruit Hunting Tour at Grimal Grove

Visit the only Breadfruit Grove in Continental United States! While here, discover the rich history of Grimal Grove and its legendary founder, Adolf Grimal, on...

1 hour 30 minutes Free Cancellation

5.0 (21)

from
$41

Private 90-Minute Harbor Sailing Charter in Key West

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida …More

4.9 (20)

Private 90-Minute Harbor Sailing Charter in Key West

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida...

1 hour 30 minutes Free Cancellation

4.9 (20)

from
$425

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

4.8 (20)

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...

2 hours 30 minutes Free Cancellation

4.8 (20)

from
$145

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

5.0 (20)

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...

2 hours Free Cancellation

5.0 (20)

from
$35

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

4.8 (19)

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...

1 hour 30 minutes Free Cancellation

4.8 (19)

from
$49

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

5.0 (19)

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...

1 hour Free Cancellation

5.0 (19)

from
$325

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

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

4.9 (14)

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...

3 hours

4.9 (14)

from
$127

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

5.0 (13)

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...

2 hours Free Cancellation

5.0 (13)

from
$599

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

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

4.9 (10)

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...

8 hours Free Cancellation

4.9 (10)

from
$250

Key West Boat Experience — Swim, Sip & Soak Up the Sun!

Welcome to Key West Boat & Jet Ski Adventures! Explore Key West's Backcountry Aboard Our Brand-New Manitou Cruise with Swim Deck Set out on a …More

4.9 (9)

Key West Boat Experience — Swim, Sip & Soak Up the Sun!

Welcome to Key West Boat & Jet Ski Adventures! Explore Key West's Backcountry Aboard Our Brand-New Manitou Cruise with Swim Deck Set out on a...

4 hours Free Cancellation

4.9 (9)

from
$600

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

5.0 (9)

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...

4 hours Free Cancellation

5.0 (9)

from
$130