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 →

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

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

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 (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

Mega Bite Dolphin Tour Boat in Clearwater Beach

50-foot shark themed vessel. The only shark that dolphins love, producing a "MEGA" wake that dolphins love to jump and play in. Covered vessel with …More

Clearwater, USA

4.8 (641)

Mega Bite Dolphin Tour Boat in Clearwater Beach

50-foot shark themed vessel. The only shark that dolphins love, producing a "MEGA" wake that dolphins love to jump and play in. Covered vessel with...

1 hour Free Cancellation

4.8 (641)

from
$28

Tropical Buffet Cruise in Clearwater Beach

If you are joining another party or reservation, please note the reservation name in the "Special Requirements" section on the booking page. This casual cruise offers you …More

Clearwater, USA

4.4 (2,279)

Tropical Buffet Cruise in Clearwater Beach

If you are joining another party or reservation, please note the reservation name in the "Special Requirements" section on the booking page. This casual cruise offers you...

2 hours Free Cancellation

4.4 (2,279)

from
$49

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar. …More

Key West, USA

4.4 (1,933)

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar....

2 hours Free Cancellation

4.4 (1,933)

from
$93

Enjoy family-friendly fun with education as you explore the amazing Everglades by airboat & see native animals both in their natural settings and up close. …More

Special Offer

Everglades National Park, USA

4.3 (718)

Miami Everglades Airboat Tour

Enjoy family-friendly fun with education as you explore the amazing Everglades by airboat & see native animals both in their natural settings and up close....

Free Cancellation

4.3 (718)

~~$33~~
$31

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

Experience the beauty of Naples, Florida while cruising on the iconic Double Sunshine. This 90-minute sightseeing cruise takes you from historic Tin City Shops out …More

Naples, USA

4.7 (1,155)

Naples Sightseeing Boat Tour

Experience the beauty of Naples, Florida while cruising on the iconic Double Sunshine. This 90-minute sightseeing cruise takes you from historic Tin City Shops out...

1 hour 30 minutes

4.7 (1,155)

from
$56

Sea Screamer Clearwater's Only Speed Boat Dolphin Watching

Sea Screamer is the largest, most exciting dolphin tour in Clearwater! Our speed(over 20 kts) and offshore Deep-V design covers more of the Gulf of …More

Clearwater, USA

4.9 (411)

Sea Screamer Clearwater's Only Speed Boat Dolphin Watching

Sea Screamer is the largest, most exciting dolphin tour in Clearwater! Our speed(over 20 kts) and offshore Deep-V design covers more of the Gulf of...

1 hour Free Cancellation

4.9 (411)

from
$40

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

Dolphin Racer Adventure Cruise in St. Pete

Join your captain on a boat ride with dolphins on the scenic waterways surrounding the beautiful Gulf beaches. Your narrated cruise is sure to be …More

St Petersburg, USA

4.8 (414)

Dolphin Racer Adventure Cruise in St. Pete

Join your captain on a boat ride with dolphins on the scenic waterways surrounding the beautiful Gulf beaches. Your narrated cruise is sure to be...

1 hour 30 minutes Free Cancellation

4.8 (414)

from
$30

Airboat Adventure in Saint Augustine with a Guide

This Sea Dragon Airboat Safari is among the most exciting fresh water tours that Florida has to offer. Experience the freshwater tributaries along the beautiful and …More

St Augustine, USA

4.8 (1,059)

Airboat Adventure in Saint Augustine with a Guide

This Sea Dragon Airboat Safari is among the most exciting fresh water tours that Florida has to offer. Experience the freshwater tributaries along the beautiful and...

1 hour 30 minutes Free Cancellation

4.8 (1,059)

from
$80

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

Key West, USA

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 Signature Sunset Sail with Live Music, Open Bar & Food

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • …More

Key West, USA

4.6 (432)

Key West Signature Sunset Sail with Live Music, Open Bar & Food

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...

2 hours Free Cancellation

4.6 (432)

from
$77

Miami Everglades Airboat Adventure with Transport

Enjoy family-friendly fun with education as you explore the amazing Everglades by airboat & see native animals both in their natural settings and up close. …More

Special Offer

Everglades National Park, USA

4.3 (718)

Miami Everglades Airboat Adventure with Transport

Enjoy family-friendly fun with education as you explore the amazing Everglades by airboat & see native animals both in their natural settings and up close....

4 hours 30 minutes (approx.) Hotel pickup offered Free Cancellation

4.3 (718)

~~$65~~
$55

Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise …More

Special Offer

Key West, USA

4.9 (128)

Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise...

2 hours (approx.) Hotel pickup offered Free Cancellation

4.9 (128)

~~$99~~
$89

Everglades Holiday Park Airboat Tours & Rides

Explore the Florida Everglades at Everglades Holiday Park located in Fort Lauderdale with an Airboat Tour, Start your experience by gliding across the River of …More

Fort Lauderdale, USA

4.4 (1,784)

Everglades Holiday Park Airboat Tours & Rides

Explore the Florida Everglades at Everglades Holiday Park located in Fort Lauderdale with an Airboat Tour, Start your experience by gliding across the River of...

1 hour 30 minutes Free Cancellation

4.4 (1,784)

from
$47

Pirate Adventure Cruise - John's Pass, Madeira Beach, FL

Ready yer sea legs and leave the landlubbers behind as you step aboard the 2-level, 46-foot U.S. Coast Guard inspected Royal Conquest Pirate Ship at …More

St Petersburg, USA

4.8 (233)

Pirate Adventure Cruise - John's Pass, Madeira Beach, FL

Ready yer sea legs and leave the landlubbers behind as you step aboard the 2-level, 46-foot U.S. Coast Guard inspected Royal Conquest Pirate Ship at...

1 hour 30 minutes Free Cancellation

4.8 (233)

from
$49

Get lost with the glorious wonder of St. Augustine's attractions. Our Adults Only 21+ option on vessel GREAT BLUE HERON is specifically made for the …More

St Augustine, USA

4.9 (1,401)

Sunset Cruise of St. Augustine

Get lost with the glorious wonder of St. Augustine's attractions. Our Adults Only 21+ option on vessel GREAT BLUE HERON is specifically made for the...

1 hour 30 minutes Free Cancellation

4.9 (1,401)

from
$43

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?