Top Key West Luxury Tours

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Key West Adventures

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Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
Special Offer
Special Offer
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
7 hours • Hotel pickup offered • Free Cancellation
7 hours • Hotel pickup offered • Free Cancellation
4.9 (37)
$169
$168
Marathon to Key West Private Tour of Florida Keys
Special Offer
Special Offer
5.0 (28)

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
8 hours • Free Cancellation
8 hours • Free Cancellation
5.0 (28)
$137
$136
Cruisin Tikis Marathon - Sunset Tiki Cruise
Special Offer
Special Offer
5.0 (27)

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
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (27)
$99
$98
Sweet Treats of Key West: A Tasty Walking Tour of Old Town
Special Offer
Special Offer
4.7 (20)

Sweet Treats of Key West: A Tasty Walking Tour of Old Town

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...

90 to 120 minutes • Free Cancellation
90 to 120 minutes • Free Cancellation
90 to 120 minutes • Free Cancellation
4.7 (20)
$70
$69
Private Key West Sunset Sail
Likely to Sell Out
Likely to Sell Out
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
2 hours
2 hours
4.9 (50)
$695
$694
The Hemingway Experience in Key West
Likely to Sell Out
Likely to Sell Out
4.9 (55)

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 hours • Free Cancellation
4 hours • Free Cancellation
4.9 (55)
$185
$184
Key West Clear Kayak Eco Tour
Special Offer
Special Offer
4.6 (39)

Key West Clear Kayak Eco Tour

Discover the natural beauty of Key West on our 2-Hour Guided Clear Kayak Eco Tour. Paddle through crystal-clear waters in a completely transparent bottom kayak,...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.6 (39)
$60
$59
Private 90-Minute Harbor Sailing Charter in Key West
Special Offer
Special Offer
4.9 (19)

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
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (19)
$395
$394
PRIVATE Welcome to Key West Walking Tour
Likely to Sell Out
Likely to Sell Out
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
90 to 180 minutes • Free Cancellation
90 to 180 minutes • Free Cancellation
4.9 (22)
$137.50
$136.50
Key West’s Old Town Treasures: A Self-Guided Audio Tour
Special Offer
Special Offer
4.3 (30)

Key West’s Old Town Treasures: A Self-Guided Audio Tour

See Key West’s top attractions from the Lighthouse to the Little White House at your own pace with this affordable walking tour. • Find out...

90 to 120 minutes • Free Cancellation
90 to 120 minutes • Free Cancellation
90 to 120 minutes • Free Cancellation
4.3 (30)
$14.99
$13.99
Key West Nighttime Full Moon Sail
Likely to Sell Out
Likely to Sell Out
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
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (10)
$83.85
$82.85
PRIVATE Key West Haunted History Walking Tour
Likely to Sell Out
Likely to Sell Out
5.0 (10)

PRIVATE Key West Haunted History Walking Tour

Walk through Old Town Key West with a long-time local, hear the haunted history of Key West, her beautiful historic mansions, and visit a haunted...

90 to 120 minutes • Free Cancellation
90 to 120 minutes • Free Cancellation
90 to 120 minutes • Free Cancellation
5.0 (10)
$137.50
$136.50
Hemingway Tour
Likely to Sell Out
Likely to Sell Out
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
1 hour 5 minutes • Free Cancellation
1 hour 5 minutes • Free Cancellation
4.7 (13)
$69
$68
Florida Keys Backcountry Eco Tour from Big Pine Key
Special Offer
Special Offer
5.0 (31)

Florida Keys Backcountry Eco Tour from Big Pine Key

This 2 hour Eco Tour will take you by boat to explore the Backcountry of the Florida Keys. We will cruise through the mangrove islands...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (31)
$450
$449
Key West Christmas Cruise with Live Band and Drinks
Likely to Sell Out
Likely to Sell Out
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
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (5)
$97.61
$96.61
Sandbar Adventure Cruise in the Florida Keys
Likely to Sell Out
Likely to Sell Out
4.9 (12)

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 hours • Free Cancellation
4 hours • Free Cancellation
4.9 (12)
$80.58
$79.58
Private Boat Tour of Flagler's Famous Bridges from Big Pine Key
Special Offer
Special Offer
5.0 (18)

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
1 hour • Free Cancellation
1 hour • Free Cancellation
5.0 (18)
$400
$399
Escape Rooms Outdoors on the Waters of Key West!
Likely to Sell Out
Likely to Sell Out
5.0 (4)

Escape Rooms Outdoors on the Waters of Key West!

Choose your adventure! Castaway, Mermaid, or Conch Quest !! Each charter is four (4) hours, with the escape game being one hour of the adventure...

4 hours • Free Cancellation
4 hours • Free Cancellation
4 hours • Free Cancellation
5.0 (4)
$500
$499
Key West Boat Experience — Swim, Sip & Soak Up the Sun!
Special Offer
Special Offer
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 hours • Free Cancellation
4 hours • Free Cancellation
4.9 (9)
$600
$599
Dry Tortugas National Park Day Trip by Luxury Private Boat
Special Offer
Special Offer
4.9 (8)

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
8 hours • Free Cancellation
8 hours • Free Cancellation
4.9 (8)
$1,500
$1,499

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