Top Florida Cruises, Sailing & Water Tours

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

Florida Cruises, Sailing & Water Tours with Instant Confirmation include: Key West Wind & Wine Sunset Sail Miami to Key West Day Trip & Glass Bottom Boat Cruise Combo Jungle Queen Riverboat 90-Minute Narrated Sightseeing Cruise in Fort Lauderdale Key West Sail, Snorkel, Kayak with Sunset Option Key West Backcountry Safari View all Tours with Instant Confirmation →

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 →

Blue Angels Practice on a Private Yacht with Captain

Indulge in a luxurious private yacht charter aboard the Mila Yenin, where elegance meets adventure. Cruise the stunning Pensacola Bay and intracoastal waterway, anchoring at …More

Pensacola, USA

5.0 (1)

Blue Angels Practice on a Private Yacht with Captain

Indulge in a luxurious private yacht charter aboard the Mila Yenin, where elegance meets adventure. Cruise the stunning Pensacola Bay and intracoastal waterway, anchoring at...

3 hours Free Cancellation

5.0 (1)

from
$900

Crystal River Sunset Kayak Rental Three Sisters Springs

This exclusive sunset single person sit on top kayak experience lets couples and close friends explore Crystal River’s National Wildlife Refuge and the world-famous Three …More

Crystal River, USA

5.0 (1)

Crystal River Sunset Kayak Rental Three Sisters Springs

This exclusive sunset single person sit on top kayak experience lets couples and close friends explore Crystal River’s National Wildlife Refuge and the world-famous Three...

2 to 4 hours Free Cancellation

5.0 (1)

from
$40

Last Chance TAILFINS TIKIS 2 Hour Crab Island ️Tiki Tour

SWIM, FLOAT, CHILL @CRABISLAND on TAILFINS TIKIS: Destin's custom Tikis to Crab Island. As seen on National News, Tailfins Tikis is the best Crab Island …More

Destin, USA

5.0 (6)

Last Chance TAILFINS TIKIS 2 Hour Crab Island ️Tiki Tour

SWIM, FLOAT, CHILL @CRABISLAND on TAILFINS TIKIS: Destin's custom Tikis to Crab Island. As seen on National News, Tailfins Tikis is the best Crab Island...

2 hours Free Cancellation

5.0 (6)

from
$90

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

Key West, USA

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

2 Hour Private Boat Charter on Clearwater Beach

Skip the crowded pontoon boats and step aboard a private 6-passenger Sea Ray designed for a more personal and unforgettable day on the water. Smaller, …More

Clearwater, USA

5.0 (1)

2 Hour Private Boat Charter on Clearwater Beach

Skip the crowded pontoon boats and step aboard a private 6-passenger Sea Ray designed for a more personal and unforgettable day on the water. Smaller,...

2 hours Free Cancellation

5.0 (1)

from
$350

Clear Kayak Three Sisters Springs Guided Summer Swim Tour

At Manatee Paddle, we provide you with our brand new fleet of clear-bottom kayaks for an unforgettable experience. This is a summer swim tour, and …More

Crystal River, USA

5.0 (3)

Clear Kayak Three Sisters Springs Guided Summer Swim Tour

At Manatee Paddle, we provide you with our brand new fleet of clear-bottom kayaks for an unforgettable experience. This is a summer swim tour, and...

2 hours 15 minutes Free Cancellation

5.0 (3)

from
$69

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

Key West, USA

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

Naples Private Boat Charter with Keewaydin Beach Setup

Begin your private charter with a scenic cruise through Naples Bay and the waterways of Port Royal, home to some of Naples' most impressive waterfront …More

Naples, USA

5.0 (3)

Naples Private Boat Charter with Keewaydin Beach Setup

Begin your private charter with a scenic cruise through Naples Bay and the waterways of Port Royal, home to some of Naples' most impressive waterfront...

4 hours Free Cancellation

5.0 (3)

from
$680

Private 4 Hour Snorkel and Sandbar Charter in Islamorada

Cruise to the Famous Islamorada Sandbar Come aboard for a fantastic cruise to the world-famous Islamorada Sandbar — the ultimate island escape! We depart from …More

Islamorada, USA

5.0 (1)

Private 4 Hour Snorkel and Sandbar Charter in Islamorada

Cruise to the Famous Islamorada Sandbar Come aboard for a fantastic cruise to the world-famous Islamorada Sandbar — the ultimate island escape! We depart from...

4 hours Free Cancellation

5.0 (1)

from
$749

You and your friends and family (up to 6 people) will love this memorable, fun, and laid-back boat cruise around the waterways of Naples on …More

Naples, USA

5.0 (2)

Tiki Boat Cruise Private Charter Tour

You and your friends and family (up to 6 people) will love this memorable, fun, and laid-back boat cruise around the waterways of Naples on...

2 hours Free Cancellation

5.0 (2)

from
$398

Private Brunch Cruise Fort Lauderdale Millionaires Row Mansions

Enjoy a relaxed, private brunch cruise along Fort Lauderdale’s scenic waterways. Glide past superyachts on the Intracoastal and up the New River. The mansions of …More

Fort Lauderdale, USA

5.0 (1)

Private Brunch Cruise Fort Lauderdale Millionaires Row Mansions

Enjoy a relaxed, private brunch cruise along Fort Lauderdale’s scenic waterways. Glide past superyachts on the Intracoastal and up the New River. The mansions of...

2 hours Free Cancellation

5.0 (1)

from
$115

Private Naples Keewaydin Island Adventures Tours

Explore Naples’ coastline with exclusive boat tours tailored for your group. Embark on an adventurous excursion to Keewaydin and other hidden islands. We guarantee a …More

Naples, USA

5.0 (1)

Private Naples Keewaydin Island Adventures Tours

Explore Naples’ coastline with exclusive boat tours tailored for your group. Embark on an adventurous excursion to Keewaydin and other hidden islands. We guarantee a...

5 hours Free Cancellation

5.0 (1)

from
$700

Private Boca Raton Deep Sea Fishing Trips

Experience South Florida's offshore waters on a private deep sea fishing trip from Boca Raton. With convenient access to the inlet, you'll spend less time …More

Boca Raton, USA

5.0 (5)

Private Boca Raton Deep Sea Fishing Trips

Experience South Florida's offshore waters on a private deep sea fishing trip from Boca Raton. With convenient access to the inlet, you'll spend less time...

4 to 6 hours Free Cancellation

5.0 (5)

from
$200

Self-Guided Kayaking Manatee and Dolphin Tour

A1A Outdoor Center is the area leader in organized outdoor activities, wildlife kayak tours and other biking and waterports activities. On this tour, we'll deliver …More

Cape Canaveral, USA

4.4 (10)

Self-Guided Kayaking Manatee and Dolphin Tour

A1A Outdoor Center is the area leader in organized outdoor activities, wildlife kayak tours and other biking and waterports activities. On this tour, we'll deliver...

1 to 3 hours Free Cancellation

4.4 (10)

from
$55

Fully Guided Kayaking Backwater Manatee and Dolphin Tour

With 15+ years of faithful service, A1A Outdoor Center has earned the title, "Most Respected Tour" for a reason. We treat our guests like family. …More

Cape Canaveral, USA

4.5 (17)

Fully Guided Kayaking Backwater Manatee and Dolphin Tour

With 15+ years of faithful service, A1A Outdoor Center has earned the title, "Most Respected Tour" for a reason. We treat our guests like family....

120 to 150 minutes Free Cancellation

4.5 (17)

from
$75

Private Titusville Florida Inshore Fishing Tour

Explore Florida's Space Coast on a private Titusville inshore fishing charter through the Indian River Lagoon and surrounding backwaters. These scenic waterways offer diverse fishing …More

Cocoa Beach, USA

5.0 (2)

Private Titusville Florida Inshore Fishing Tour

Explore Florida's Space Coast on a private Titusville inshore fishing charter through the Indian River Lagoon and surrounding backwaters. These scenic waterways offer diverse fishing...

4 to 6 hours Free Cancellation

5.0 (2)

from
$258

Private Clearwater Inshore Fishing Charter

Experience Clearwater from the water on a private inshore fishing charter exploring Clearwater Bay, nearby barrier islands, and the waters surrounding Caladesi Island. This diverse …More

Clearwater, USA

5.0 (7)

Private Clearwater Inshore Fishing Charter

Experience Clearwater from the water on a private inshore fishing charter exploring Clearwater Bay, nearby barrier islands, and the waters surrounding Caladesi Island. This diverse...

4 to 6 hours Free Cancellation

5.0 (7)

from
$225

Private Daytona Beach Inshore Fishing Charter

Experience Daytona Beach beyond the shoreline on a private inshore fishing charter through the scenic Halifax River and surrounding backwaters. Just minutes from Daytona's famous …More

Daytona Beach, USA

5.0 (1)

Private Daytona Beach Inshore Fishing Charter

Experience Daytona Beach beyond the shoreline on a private inshore fishing charter through the scenic Halifax River and surrounding backwaters. Just minutes from Daytona's famous...

4 to 6 hours Free Cancellation

5.0 (1)

from
$200

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

Key West, USA

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

Explore the wild side of Southwest Florida on a private Naples inshore fishing charter through the legendary Ten Thousand Islands. This remarkable coastal ecosystem features …More

Naples, USA

5.0 (5)

Private Naples Inshore Fishing Charters

Explore the wild side of Southwest Florida on a private Naples inshore fishing charter through the legendary Ten Thousand Islands. This remarkable coastal ecosystem features...

4 to 6 hours Free Cancellation

5.0 (5)

from
$238

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?

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?