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 →

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

Key West, USA

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

Dolphin and Shelling Cruise for up to 12 people

Experience the best of Marco Island’s waterways on Eco Endeavors’ Dolphin & Shelling Tour! This 2.5-hour adventure takes you deep into the Ten Thousand Islands …More

Naples, USA

4.9 (992)

Dolphin and Shelling Cruise for up to 12 people

Experience the best of Marco Island’s waterways on Eco Endeavors’ Dolphin & Shelling Tour! This 2.5-hour adventure takes you deep into the Ten Thousand Islands...

2 hours 30 minutes Free Cancellation

4.9 (992)

from
$109

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

Key West, USA

4.9 (985)

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 (985)

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

Key West, USA

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

Backwater Adventure's CraigCat Tours of the 10,000 Islands

Operate your own 2 person catamaran through the winding and breathtaking waterways of the 10,000 Islands. Excitement, tranquility, thrill, and intimacy bundled in to one …More

Naples, USA

4.9 (967)

Backwater Adventure's CraigCat Tours of the 10,000 Islands

Operate your own 2 person catamaran through the winding and breathtaking waterways of the 10,000 Islands. Excitement, tranquility, thrill, and intimacy bundled in to one...

90 to 150 minutes Free Cancellation

4.9 (967)

from
$165

Glass Bottom Kayak Eco Tour through Rainbow Springs

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

Orlando, USA

4.9 (929)

Glass Bottom Kayak Eco Tour through Rainbow Springs

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

2 hours

4.9 (929)

from
$89

Mangrove Tunnels, Dolphins, Manatee Tour #1 Rated in Cocoa Beach

#1 rated Fin Expeditions' goal is to treat everyone like family. Come experience and learn about the magical mangrove tunnels or bioluminescence. Enjoy dolphins or …More

Cocoa Beach, USA

5.0 (918)

Mangrove Tunnels, Dolphins, Manatee Tour #1 Rated in Cocoa Beach

#1 rated Fin Expeditions' goal is to treat everyone like family. Come experience and learn about the magical mangrove tunnels or bioluminescence. Enjoy dolphins or...

2 hours Free Cancellation

5.0 (918)

from
$65

Welcome to our enchanted 32-acre park, where adventure awaits around every corner. Explore the lighted brick pathways that wind along the beautiful lake, surrounded by …More

Orlando, USA

4.9 (890)

One-Hour Airboat Ride Near Orlando

Welcome to our enchanted 32-acre park, where adventure awaits around every corner. Explore the lighted brick pathways that wind along the beautiful lake, surrounded by...

1 hour Free Cancellation

4.9 (890)

from
$66

Mangrove Tunnels & Mudflats Kayak Tour - Local Biologist Guides

Join SWFL's only active local biologist guides for an adventure through the Rookery Bay Reserve at the start of the 10,000 islands on the #1 …More

Naples, USA

5.0 (830)

Mangrove Tunnels & Mudflats Kayak Tour - Local Biologist Guides

Join SWFL's only active local biologist guides for an adventure through the Rookery Bay Reserve at the start of the 10,000 islands on the #1...

2 hours 30 minutes Free Cancellation

5.0 (830)

from
$75

Soar above Clearwater Beach with the top-rated parasailing experience in the area. Enjoy breathtaking panoramic views of the coastline, the Gulf, and the surrounding islands …More

Clearwater, USA

5.0 (780)

Clearwater Beach Parasailing Experience

Soar above Clearwater Beach with the top-rated parasailing experience in the area. Enjoy breathtaking panoramic views of the coastline, the Gulf, and the surrounding islands...

1 hour 15 minutes Free Cancellation

5.0 (780)

from
$91

Experience the thrill of dolphin-watching with Hydrojet on an excursion that navigates Crab Island, showcases a scenic cruise of Destin Harbor, and traverses the East …More

Destin, USA

4.9 (775)

Dolphin Cruise in Destin FL

Experience the thrill of dolphin-watching with Hydrojet on an excursion that navigates Crab Island, showcases a scenic cruise of Destin Harbor, and traverses the East...

1 hour Free Cancellation

4.9 (775)

from
$35

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

Key West, USA

4.8 (752)

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 (752)

from
$90

Sunset Dolphin Sail Aboard the Privateer Catamaran

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, …More

Panama City Beach, USA

4.8 (750)

Sunset Dolphin Sail Aboard the Privateer Catamaran

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer,...

2 hours Free Cancellation

4.8 (750)

from
$43

Clear Kayak Sunset & Glow Tours of Shell Key Preserve

Sunset Tour: Enjoy a picturesque sunset before darkness falls & Watch the sunset from the beautiful beach on Shell Key. As night falls, your LED …More

St Petersburg, USA

5.0 (749)

Clear Kayak Sunset & Glow Tours of Shell Key Preserve

Sunset Tour: Enjoy a picturesque sunset before darkness falls & Watch the sunset from the beautiful beach on Shell Key. As night falls, your LED...

1 hour 30 minutes Free Cancellation

5.0 (749)

from
$89

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

Key West, USA

4.9 (740)

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 (740)

from
$89

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

Key West, USA

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

Small group Manatee Tour with In-Water Divemaster/Photographer

Just like our regular tours, you can swim alongside manatees for even longer. Only 6 people per vessel allows for a more personal experience The …More

Crystal River, USA

5.0 (731)

Small group Manatee Tour with In-Water Divemaster/Photographer

Just like our regular tours, you can swim alongside manatees for even longer. Only 6 people per vessel allows for a more personal experience The...

3 hours Free Cancellation

5.0 (731)

from
$99

Private Sunset or Night Boat Cruise in Miami

Get your phone ready for an epic Instagram photo on this unique experience that will bring our customers to one of the most astonishing skylines …More

Miami, USA

5.0 (731)

Private Sunset or Night Boat Cruise in Miami

Get your phone ready for an epic Instagram photo on this unique experience that will bring our customers to one of the most astonishing skylines...

2 hours Free Cancellation

5.0 (731)

from
$215

2 Hour Sunset Cruise in Clearwater, Florida

Our Evening Sunset Cruise is a 2 hour cruise of the Intracoastal Waterway, Clearwater Pass, and into the Gulf of Mexico (weather permitting). Your crew …More

Clearwater, USA

4.8 (712)

2 Hour Sunset Cruise in Clearwater, Florida

Our Evening Sunset Cruise is a 2 hour cruise of the Intracoastal Waterway, Clearwater Pass, and into the Gulf of Mexico (weather permitting). Your crew...

2 hours Free Cancellation

4.8 (712)

from
$40

Miami Sunset Champagne Cruise with Skyline Views

This 90 minute boat tour takes you through the sparkling waters of Biscayne Bay, offering panoramic views of the Miami skyline, city lights, and world …More

Miami, USA

4.9 (704)

Miami Sunset Champagne Cruise with Skyline Views

This 90 minute boat tour takes you through the sparkling waters of Biscayne Bay, offering panoramic views of the Miami skyline, city lights, and world...

1 hour 20 minutes Free Cancellation

4.9 (704)

from
$30

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?