Top Key West Cruises, Sailing & Water Tours

Q: Which Key West Cruises, Sailing & Water Tours have Instant Confirmation?

Key West Cruises, Sailing & Water Tours with Instant Confirmation include: Key West Wind & Wine Sunset Sail Key West Sail, Snorkel, Kayak with Sunset Option Key West Backcountry Safari Key West Mangrove Kayak Eco Tour Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar View all Tours with Instant Confirmation →

Q: I need a ride! Which Key West Cruises, Sailing & Water Tours have Hotel Pickup?

No problem. These Key West Cruises, Sailing & Water Tours include Hotel Pickup: Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location Key West Dolphin Watch & Snorkel with FREE shuttle to location 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 →

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 Hidden Sanctuary Mangrove Kayak Tour With Drinks

Key West’s Most Secluded Kayak & Sandbar Adventure Escape the crowds and explore Key West’s most secluded kayak tour in the Florida Marine Sanctuary. Unlike …More

4.6 (9)

Key West Hidden Sanctuary Mangrove Kayak Tour With Drinks

Key West’s Most Secluded Kayak & Sandbar Adventure Escape the crowds and explore Key West’s most secluded kayak tour in the Florida Marine Sanctuary. Unlike...

5 hours Free Cancellation

4.6 (9)

from
$161

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

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

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

2 Hour Mangrove Maze Kayak Tour in Key West

Navigate through the stunning Mangrove Tunnels on this engaging 2-hour kayak tour in Key West. Ideal for all ages and skill levels, this adventure allows …More

5.0 (9)

2 Hour Mangrove Maze Kayak Tour in Key West

Navigate through the stunning Mangrove Tunnels on this engaging 2-hour kayak tour in Key West. Ideal for all ages and skill levels, this adventure allows...

2 hours Free Cancellation

5.0 (9)

from
$65

Key West 3-Hour Private Dolphin-Watching Boat Charter

This three-hour private Key West dolphin safari combines wildlife searching with the flexibility of a private boat charter. Rather than following a fixed group-tour route, …More

5.0 (2)

Key West 3-Hour Private Dolphin-Watching Boat Charter

This three-hour private Key West dolphin safari combines wildlife searching with the flexibility of a private boat charter. Rather than following a fixed group-tour route,...

3 hours Free Cancellation

5.0 (2)

from
$895

Key West Ultimate Beach Pass with Parasailing

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass. …More

4.7 (19)

Key West Ultimate Beach Pass with Parasailing

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass....

8 hours Free Cancellation

4.7 (19)

from
$107

Private Sandbar Charter & Island Escape in Key West

Explore the crystal-clear waters and pristine sandbar islands that surround the Florida Keys. This private sandbar charter is fully customizable—whether you’re looking to relax with …More

5.0 (2)

Private Sandbar Charter & Island Escape in Key West

Explore the crystal-clear waters and pristine sandbar islands that surround the Florida Keys. This private sandbar charter is fully customizable—whether you’re looking to relax with...

4 hours Free Cancellation

5.0 (2)

from
$800

PRIVATE Guided Mangrove Eco-Tour Adventure

Paddle through the serene waters of Geiger Key at your own pace, with a private guided kayak/Paddleboard tour that immerses you in the natural beauty …More

5.0 (2)

PRIVATE Guided Mangrove Eco-Tour Adventure

Paddle through the serene waters of Geiger Key at your own pace, with a private guided kayak/Paddleboard tour that immerses you in the natural beauty...

2 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$395

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

Private Marathon Offshore Fishing Charter

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish! Marathon the hub for fishing in the Keys, great beaches, shopping, and …More

5.0 (2)

Private Marathon Offshore Fishing Charter

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish! Marathon the hub for fishing in the Keys, great beaches, shopping, and...

4 hours Free Cancellation

5.0 (2)

from
$217

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch …More

5.0 (1)

Private Sunset Sail in Key West Florida

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch...

2 hours Free Cancellation

5.0 (1)

from
$750

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

Experience the Florida Keys from the water on a private Marathon inshore fishing charter surrounded by turquoise seas, tropical scenery, and diverse fishing opportunities. Marathon's …More

5.0 (1)

Private Marathon Inshore Fishing Charter

Experience the Florida Keys from the water on a private Marathon inshore fishing charter surrounded by turquoise seas, tropical scenery, and diverse fishing opportunities. Marathon's...

4 to 8 hours Free Cancellation

5.0 (1)

from
$250

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 Cruises, Sailing & Water Tours?

What are the best kid-friendly options for Key West Cruises, Sailing & Water Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Key West Cruises, Sailing & Water Tours are:

View all kid-friendly Tours →

Which Key West Cruises, Sailing & Water Tours have Instant Confirmation?

Which Key West Cruises, Sailing & Water Tours have Free Cancellation?

Key West Cruises, Sailing & Water Tours 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 Cruises, Sailing & Water Tours have Hotel Pickup?

Got any more Key West trip ideas?

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