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 Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar Shark and Wildlife Viewing Adventure in Key West Key West Sail, Snorkel, Kayak with Sunset Option Key West Backcountry Safari Key West Mangrove Kayak Eco Tour 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 →

Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran …More

4.8 (3,832)

Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...

2 hours (approx.) Free Cancellation

4.8 (3,832)

from
$80

Shark and Wildlife Viewing Adventure in Key West

This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to …More

5.0 (3,311)

Shark and Wildlife Viewing Adventure in Key West

This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to...

2 hours Free Cancellation

5.0 (3,311)

from
$99

Key West Sail, Snorkel, Kayak with Sunset Option

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge. …More

4.9 (2,739)

Key West Sail, Snorkel, Kayak with Sunset Option

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4.5 or 6.5 hours (approx.) Free Cancellation

4.9 (2,739)

from
$105

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness. …More

4.9 (2,739)

Key West Backcountry Safari

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....

4.5 or 6.5 hours (approx.) Free Cancellation

4.9 (2,739)

from
$105

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 (2,388)

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 (2,388)

from
$80

Wind & Wine has been the #1 rated sunset sail on Cool Shore Excursions for over a decade. In our opinion, this is the best …More

5.0 (1,717)

Key West Wind & Wine Sunset Sail

Wind & Wine has been the #1 rated sunset sail on Cool Shore Excursions for over a decade. In our opinion, this is the best...

2 hours (approx.) Free Cancellation

5.0 (1,717)

~~$115~~
$99

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Shore Excursions three years running. See the sunset …More

5.0 (1,717)

Key West Private Wind & Wine Charter

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Shore Excursions three years running. See the sunset...

2 hours (approx.) Free Cancellation

5.0 (1,717)

from
$3,499

Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and …More

4.9 (1,703)

Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...

2 hours (approx.) Free Cancellation

4.9 (1,703)

from
$100

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key …More

4.9 (1,703)

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...

2 hours Free Cancellation

4.9 (1,703)

from
$127

Key West "Commotion on the Ocean" Live Music Sunset Sail

This is the Key West sunset cruise party everyone talks about — live music, open-bar beer, wine, & margaritas, delicious appetizers, dancing, and a great …More

4.8 (996)

Key West "Commotion on the Ocean" Live Music Sunset Sail

This is the Key West sunset cruise party everyone talks about — live music, open-bar beer, wine, & margaritas, delicious appetizers, dancing, and a great...

2 Hours (approx.) Free Cancellation

4.8 (996)

from
$80

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

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne …More

4.9 (977)

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne...

2 hours

4.9 (977)

from
$109

Key West Catamaran Dolphin Watch & Sunset Sail

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines …More

4.8 (750)

Key West Catamaran Dolphin Watch & Sunset Sail

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines...

2 hours 30 minutes (approx.) Free Cancellation

4.8 (750)

from
$90

Key West Original Full-Day Watersports Adventure

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the …More

Special Offer

4.9 (739)

Key West Original Full-Day Watersports Adventure

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the...

6 hours (approx.) Free Cancellation

4.9 (739)

~~$200~~
$169

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

All-Inclusive Sandbar Safari with Dolphin Playground Encounter

Embark on a journey like no other. This tour takes guests on an amazing journey from Key West to a secluded sandbar & then to …More

4.9 (681)

All-Inclusive Sandbar Safari with Dolphin Playground Encounter

Embark on a journey like no other. This tour takes guests on an amazing journey from Key West to a secluded sandbar & then to...

5 hours Free Cancellation

4.9 (681)

from
$150

Private Luxury Sandbar Excursion in Key West

Hey there, I’m Captain Zak; just a guy with a boat who loves showing off Key West and sharing good times on the water. Whether …More

4.9 (621)

Private Luxury Sandbar Excursion in Key West

Hey there, I’m Captain Zak; just a guy with a boat who loves showing off Key West and sharing good times on the water. Whether...

4 hours Free Cancellation

4.9 (621)

from
$1,200

Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and …More

4.9 (576)

Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and...

4 hours Free Cancellation

4.9 (576)

from
$150

Key West Full-Day Catamaran Eco Tour: Sail, Kayak and Dolphin Watch

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a …More

Special Offer

4.9 (558)

Key West Full-Day Catamaran Eco Tour: Sail, Kayak and Dolphin Watch

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a...

6 hours (approx.)

4.9 (558)

~~$125~~
$120

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both …More

4.8 (550)

Key West Reef Snorkel & Sail Adventure

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both...

3 hours Free Cancellation

4.8 (550)

from
$79

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?