Top Key West Luxury & Special Occasions

Q: Which Key West Luxury & Special Occasions have Instant Confirmation?

Key West Luxury & Special Occasions with Instant Confirmation include: Key West Mangrove Kayak Eco Tour Key West Sunset Cruise: Dinner, Live Music & Drinks Included Key West Hop-On Hop-Off Trolley Tour Key West Craft Cocktail Crawl Key West Schooner Sunset Sail with Bar & Hors d'oeuvres View all Tours with Instant Confirmation →

Q: I need a ride! Which Key West Luxury & Special Occasions have Hotel Pickup?

No problem. These Key West Luxury & Special Occasions 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 →

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

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

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

Escape Rooms Outdoors on the Waters of Key West!

Choose your adventure: Castaway (The Haunted Island), Mermaid Adventure or Gilligan's Island! Each private 3-hour charter includes a one-hour escape game played outdoors, on the …More

5.0 (5)

Escape Rooms Outdoors on the Waters of Key West!

Choose your adventure: Castaway (The Haunted Island), Mermaid Adventure or Gilligan's Island! Each private 3-hour charter includes a one-hour escape game played outdoors, on the...

3 hours Free Cancellation

5.0 (5)

from
$500

Key West UFO Skywatch Tour with Night Vision

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else …More

5.0 (1)

Key West UFO Skywatch Tour with Night Vision

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else...

1 hour 15 minutes Free Cancellation

5.0 (1)

from
$49

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

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

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

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

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 …More

5.0 (35)

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

5.0 (35)

from
$399

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

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

Experience Florida Keys Boat Charter Private Tour

Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while …More

5.0 (8)

Experience Florida Keys Boat Charter Private Tour

Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while...

1 hour 30 minutes Free Cancellation

5.0 (8)

from
$460

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

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 (19)

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 (19)

from
$145

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

Private Afternoon Snorkel with Sunset Sail in Key West

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon …More

5.0 (4)

Private Afternoon Snorkel with Sunset Sail in Key West

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon...

4 hours Free Cancellation

5.0 (4)

from
$1,070

Key West After Dark, Ghost, Santeria & Voodoo Pedicab Tour

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll …More

5.0 (7)

Key West After Dark, Ghost, Santeria & Voodoo Pedicab Tour

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll...

1 hour 30 minutes Free Cancellation

5.0 (7)

from
$158

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 (3)

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 (3)

from
$69

Half Day Luxury Boat Tour in Key West with Snorkeling

Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring …More

5.0 (3)

Half Day Luxury Boat Tour in Key West with Snorkeling

Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring...

4 hours Free Cancellation

5.0 (3)

from
$200

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Key West Luxury & Special Occasions?

What are the best kid-friendly options for Key West Luxury & Special Occasions Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Key West Luxury & Special Occasions are:

View all kid-friendly Tours →

Which Key West Luxury & Special Occasions have Instant Confirmation?

Which Key West Luxury & Special Occasions have Free Cancellation?

Key West Luxury & Special Occasions with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Key West Luxury & Special Occasions have Hotel Pickup?

Got any more Key West trip ideas?

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