Top Florida Cruises, Sailing & Water Tours

Q: Got any more Florida trip ideas?

We sure do. Check out our curated lists of hand-picked Florida Tours. Top 10 Florida 2026 Senior-friendly tours Florida Top Picks for an Orlando Everglades Airboat Adventure Top Picks for an Miami Everglades Airboat Adventure The best tours and activities for culture lovers in Florida View all Florida Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Florida?

Based on our sales data over the past year, the most popular styles of tours and activities in Florida are: Florida Kid Friendly Florida Kid Friendly Tours & Activities Florida Vehicle Rentals Florida Cruises, Sailing & Water Tours Florida Boat Tours View all tour styles in Florida →

Clear Kayak Tour of Shell Key Preserve and Tampa Bay Area

Adventure through Shell Key Preserve in your 100% clear kayak! See crystal-clear water, diverse marine life, and the underwater world below your clear kayak. You’ll …More

St Petersburg, USA

5.0 (6,767)

Clear Kayak Tour of Shell Key Preserve and Tampa Bay Area

Adventure through Shell Key Preserve in your 100% clear kayak! See crystal-clear water, diverse marine life, and the underwater world below your clear kayak. You’ll...

2 hours Free Cancellation

5.0 (6,767)

from
$89

Little Toot Dolphin Adventure at Clearwater Beach

Adults and children of all ages love the Little Toot because of our “tug boat” shape and power, we create a huge wake that Dolphins …More

Clearwater, USA

4.9 (5,824)

Little Toot Dolphin Adventure at Clearwater Beach

Adults and children of all ages love the Little Toot because of our “tug boat” shape and power, we create a huge wake that Dolphins...

1 hour 15 minutes Free Cancellation

4.9 (5,824)

from
$37

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes …More

Panama City Beach, USA

4.9 (5,050)

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes...

3 hours Free Cancellation

4.9 (5,050)

from
$52

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

Key West, USA

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

Key West, USA

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

Dolphin and Manatee Adventure Tour of Fort Myers

Come join us for a once in a lifetime experience that is great for all skill levels. There are only a few places on earth …More

Fort Myers, USA

4.9 (3,110)

Dolphin and Manatee Adventure Tour of Fort Myers

Come join us for a once in a lifetime experience that is great for all skill levels. There are only a few places on earth...

2 hours Free Cancellation

4.9 (3,110)

from
$77

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

Key West, USA

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

Key West, USA

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

Orlando Florida Everglades Airboat Tour and Wild Florida Admission with Optional Lunch

Explore the natural side of Florida and experience its peaceful beauty on an adventure through the Florida Everglades. This ultimate Florida experience includes a 30-minute …More

Orlando, USA

4.8 (2,693)

Orlando Florida Everglades Airboat Tour and Wild Florida Admission with Optional Lunch

Explore the natural side of Florida and experience its peaceful beauty on an adventure through the Florida Everglades. This ultimate Florida experience includes a 30-minute...

1 hour Free Cancellation

4.8 (2,693)

from
$37

Rock Springs 2-Hour Glass Bottom Guided Kayak Eco Tour

Enjoy a unique kayaking experience on this Small-Group Guided Glass Bottom Kayak Eco Tour of Rock Springs in Florida. Begin your tour with a quick …More

Orlando, USA

4.9 (2,532)

Rock Springs 2-Hour Glass Bottom Guided Kayak Eco Tour

Enjoy a unique kayaking experience on this Small-Group Guided Glass Bottom Kayak Eco Tour of Rock Springs in Florida. Begin your tour with a quick...

2 hours 30 minutes

4.9 (2,532)

from
$101

Manatee Swim Tour with In Water Photographer

Our Manatee Swim tour at Explorida was Voted Cool Shore Excursionss 2022 "Top Ten Bucket List Experience in THE WORLD!" Swimming with the manatees is …More

Crystal River, USA

5.0 (2,392)

Manatee Swim Tour with In Water Photographer

Our Manatee Swim tour at Explorida was Voted Cool Shore Excursionss 2022 "Top Ten Bucket List Experience in THE WORLD!" Swimming with the manatees is...

3 hours Free Cancellation

5.0 (2,392)

from
$77

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

Key West, USA

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

Island Sunset and Skyway Light Show - 3hr Boat Cruise in St. Pete

Join us on our brand new 50ft Custom Catamaran for an evening like no other! A scenic trip out the Intracoastal and along Shell Key …More

St Petersburg, USA

5.0 (2,383)

Island Sunset and Skyway Light Show - 3hr Boat Cruise in St. Pete

Join us on our brand new 50ft Custom Catamaran for an evening like no other! A scenic trip out the Intracoastal and along Shell Key...

3 hours Free Cancellation

5.0 (2,383)

from
$85

#1 VENICE OF AMERICA TOUR - Cold A/C 115' LARGEST IN LAUDERDALE!

Largest in Fort Lauderdale 115' Room to freely move around! AIR CONDITIONED - SHADE OR SUN - MOST COMFORTABLE The Carrie B sightseeing paddlewheel tour …More

Fort Lauderdale, USA

4.8 (2,300)

#1 VENICE OF AMERICA TOUR - Cold A/C 115' LARGEST IN LAUDERDALE!

Largest in Fort Lauderdale 115' Room to freely move around! AIR CONDITIONED - SHADE OR SUN - MOST COMFORTABLE The Carrie B sightseeing paddlewheel tour...

1 hour 30 minutes Free Cancellation

4.8 (2,300)

from
$32

Clearwater Encounters with Dolphins Tour

Established in 1999, Encounters With Dolphins has been safely providing guests the opportunity to view dolphins, learn about Clearwater and enjoy the sand and sun …More

Clearwater, USA

4.9 (2,273)

Clearwater Encounters with Dolphins Tour

Established in 1999, Encounters With Dolphins has been safely providing guests the opportunity to view dolphins, learn about Clearwater and enjoy the sand and sun...

1 hour 30 minutes Free Cancellation

4.9 (2,273)

from
$36

Crystal River Clear Kayak Tour: Three Sisters Springs & Manatees

Discover Florida's springs with the original clear kayak tour company in Crystal River, running since 2018. Small groups, expert local guides, and 100% clear kayaks. …More

Crystal River, USA

4.9 (2,145)

Crystal River Clear Kayak Tour: Three Sisters Springs & Manatees

Discover Florida's springs with the original clear kayak tour company in Crystal River, running since 2018. Small groups, expert local guides, and 100% clear kayaks....

2 hours Free Cancellation

4.9 (2,145)

from
$99

Private Miami Boat Charter: Sightseeing, Sunset & Sandbar

Experience Miami the way it’s meant to be seen—on your own private boat, with the flexibility to make the day exactly what you want. With …More

Miami, USA

5.0 (2,129)

Private Miami Boat Charter: Sightseeing, Sunset & Sandbar

Experience Miami the way it’s meant to be seen—on your own private boat, with the flexibility to make the day exactly what you want. With...

2 to 5 hours Free Cancellation

5.0 (2,129)

from
$199

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in …More

Panama City Beach, USA

4.9 (2,098)

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in...

2 hours Free Cancellation

4.9 (2,098)

from
$42

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

Key West, USA

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

Key West, USA

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

Frequently Asked Questions

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

What are the best options for Florida Cruises, Sailing & Water Tours?

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

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

View all kid-friendly Tours →

Which Florida Cruises, Sailing & Water Tours have Instant Confirmation?

Florida Cruises, Sailing & Water Tours with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which Florida Cruises, Sailing & Water Tours have Free Cancellation?

Florida 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 Florida Cruises, Sailing & Water Tours have Hotel Pickup?

No problem. These Florida Cruises, Sailing & Water Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Florida trip ideas?

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