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 →

Crab Island Charter, Customized for up to 30 Guests

Join us with your family and friends for an unforgettable customized adventure. Our crew will work with you to create a one of a kind …More

Destin, USA

5.0 (5)

Crab Island Charter, Customized for up to 30 Guests

Join us with your family and friends for an unforgettable customized adventure. Our crew will work with you to create a one of a kind...

4 hours Free Cancellation

5.0 (5)

from
$2,000

Private St Augustine Inshore Fishing Charters

Experience America's oldest city from a completely different perspective on a private inshore fishing charter through the historic waterways of St. Augustine. Explore scenic backwaters, …More

St Augustine, USA

4.9 (9)

Private St Augustine Inshore Fishing Charters

Experience America's oldest city from a completely different perspective on a private inshore fishing charter through the historic waterways of St. Augustine. Explore scenic backwaters,...

4 to 6 hours Free Cancellation

4.9 (9)

from
$188

Paddle Pub Clearwater Private Cruise – 2 Hours (2-20ppl, BYOB)

Explore the vibrant heart of Clearwater in style aboard your own private paddle pub boat! This charter is all yours! Set sail through the beautiful …More

Clearwater, USA

5.0 (5)

Paddle Pub Clearwater Private Cruise – 2 Hours (2-20ppl, BYOB)

Explore the vibrant heart of Clearwater in style aboard your own private paddle pub boat! This charter is all yours! Set sail through the beautiful...

2 hours Free Cancellation

5.0 (5)

from
$980

Our dolphin tour is rated #1 in the Gulf coast area. While on our brand new 45' catamaran, our experienced captain will take you out …More

Destin, USA

4.5 (13)

2 Hours Guided Dolphin Tour in Florida

Our dolphin tour is rated #1 in the Gulf coast area. While on our brand new 45' catamaran, our experienced captain will take you out...

2 hours Free Cancellation

4.5 (13)

from
$38

Private Clearwater Sunset Cruise & Dolphins (2 Hours,6 Guests)

Skip the crowded tour boats and enjoy a private Clearwater sunset cruise with exclusive use of our boat. Relax as we guide you through the …More

5.0 (5)

Private Clearwater Sunset Cruise & Dolphins (2 Hours,6 Guests)

Skip the crowded tour boats and enjoy a private Clearwater sunset cruise with exclusive use of our boat. Relax as we guide you through the...

2 hours Free Cancellation

5.0 (5)

from
$350

1.5 to 2 hour tour, leaving from from the Castaways Marina at Square Grouper Tiki Bar, of the Intercoastal waterway along Jupiter Island. Enjoy the …More

West Palm Beach, USA

4.7 (15)

Jupiter Island Water Tour

1.5 to 2 hour tour, leaving from from the Castaways Marina at Square Grouper Tiki Bar, of the Intercoastal waterway along Jupiter Island. Enjoy the...

2 hours Free Cancellation

4.7 (15)

from
$65

We want everyone to experience the beauty of Destin sunsets on the water. We provide complementary wine & snacks (21 & over for wine). We …More

Destin, USA

5.0 (6)

Serenity Sunset Cruise in Destin

We want everyone to experience the beauty of Destin sunsets on the water. We provide complementary wine & snacks (21 & over for wine). We...

1 hour 30 minutes Free Cancellation

5.0 (6)

from
$59

Private Naples Dolphin & Sunset Cruise with Charcuterie and Wine

- Entire boat reserved exclusively for your group - Your own captain and personalized experience - Search for wild dolphins and other local marine life …More

Naples, USA

5.0 (7)

Private Naples Dolphin & Sunset Cruise with Charcuterie and Wine

- Entire boat reserved exclusively for your group - Your own captain and personalized experience - Search for wild dolphins and other local marine life...

2 hours Free Cancellation

5.0 (7)

from
$462

Sunset Sail in the Gulf of Mexico for up to 6 Guests

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the …More

Fort Myers, USA

5.0 (12)

Sunset Sail in the Gulf of Mexico for up to 6 Guests

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the...

2 hours 30 minutes Free Cancellation

5.0 (12)

from
$149

Dolphin Sightseeing Tiki Boat Tour 90 minutes

Set sail on a breathtaking 90 minute tiki boat Dolphin Sightseeing tour! Our experienced Captain and Crew will cruise you through Grand Lagoon and tranquil …More

Panama City Beach, USA

5.0 (5)

Dolphin Sightseeing Tiki Boat Tour 90 minutes

Set sail on a breathtaking 90 minute tiki boat Dolphin Sightseeing tour! Our experienced Captain and Crew will cruise you through Grand Lagoon and tranquil...

1 hour 30 minutes Free Cancellation

5.0 (5)

from
$35

Private Day Cruise: Explore Cape Coral, Sanibel and Fort Myers

Embark on a guided day cruise with our licensed captain and enjoy a beautiful day on the water with your family and friends. We'll tour …More

Fort Myers, USA

5.0 (20)

Private Day Cruise: Explore Cape Coral, Sanibel and Fort Myers

Embark on a guided day cruise with our licensed captain and enjoy a beautiful day on the water with your family and friends. We'll tour...

2 to 6 hours Free Cancellation

5.0 (20)

from
$280

Set off on the beautiful Gulf waters of Panama City Beach for an unforgettable Sunset adventure. Interact with dolphins, explore the stunning Shell Island, and …More

Panama City Beach, USA

5.0 (12)

Sunset Snorkel and Dolphin Cruise

Set off on the beautiful Gulf waters of Panama City Beach for an unforgettable Sunset adventure. Interact with dolphins, explore the stunning Shell Island, and...

2 hours Free Cancellation

5.0 (12)

from
$46

Private Luxury Port Royal Real Estate Cruise

We aim to set the standard when it comes to experiencing Naples from the water. Enjoy a private and intimate experience on a luxury deck …More

Naples, USA

5.0 (6)

Private Luxury Port Royal Real Estate Cruise

We aim to set the standard when it comes to experiencing Naples from the water. Enjoy a private and intimate experience on a luxury deck...

2 hours Free Cancellation

5.0 (6)

from
$550

Private Luxury Keewaydin Island Beach & Dolphin Excursion

Discover the serene beauty of Keewaydin Island on a luxury boat tour to this hidden gem of Southwest Florida. Accessible only by boat, the island …More

Naples, USA

5.0 (9)

Private Luxury Keewaydin Island Beach & Dolphin Excursion

Discover the serene beauty of Keewaydin Island on a luxury boat tour to this hidden gem of Southwest Florida. Accessible only by boat, the island...

3 hours Free Cancellation

5.0 (9)

from
$595

Private Capt. Cruise to Crab Island(Capt. fee included in price)

Set sail from Destin to the popular Crab Island sandbar with a private captain at your service with FunDestin Adventures. Enjoy a customizable experience tailored …More

Destin, USA

5.0 (7)

Private Capt. Cruise to Crab Island(Capt. fee included in price)

Set sail from Destin to the popular Crab Island sandbar with a private captain at your service with FunDestin Adventures. Enjoy a customizable experience tailored...

4 hours Free Cancellation

5.0 (7)

from
$419

Go Tiki Tours Clearwater"#1 Floating Tiki Boat" Bathroom on Board

We provide the perfect 2 hour Floating Tiki Boat for any of your event needs… whether you're celebrating birthdays, anniversaries, graduations, retirements, or bachelor/bachelorette parties, …More

Clearwater, USA

5.0 (8)

Go Tiki Tours Clearwater"#1 Floating Tiki Boat" Bathroom on Board

We provide the perfect 2 hour Floating Tiki Boat for any of your event needs… whether you're celebrating birthdays, anniversaries, graduations, retirements, or bachelor/bachelorette parties,...

2 hours

5.0 (8)

from
$60

Dolphin Eco Cruise Nature Adventure in Cocoa Beach

Discover the beauty of Cocoa Beach on the Dolphin Eco Cruise aboard Wildside. This 2-hour adventure takes you through the scenic Thousand Islands, where you …More

Cocoa Beach, USA

5.0 (5)

Dolphin Eco Cruise Nature Adventure in Cocoa Beach

Discover the beauty of Cocoa Beach on the Dolphin Eco Cruise aboard Wildside. This 2-hour adventure takes you through the scenic Thousand Islands, where you...

2 hours Free Cancellation

5.0 (5)

from
$49

Dolphin Boat Tour on a Silent Electric Vessel – Vero Beach, FL Explore the beauty of the Indian River Lagoon aboard our elegant, whisper-quiet electric …More

Vero Beach, USA

5.0 (9)

Dolphin Boat Tour in Vero Beach

Dolphin Boat Tour on a Silent Electric Vessel – Vero Beach, FL Explore the beauty of the Indian River Lagoon aboard our elegant, whisper-quiet electric...

1 hour 30 minutes Free Cancellation

5.0 (9)

from
$344

Guided Shelling Adventure in the Ten Thousand Islands

Discover the natural beauty of the Ten Thousand Islands on a guided shelling adventure led by Master Naturalist captains. This family-friendly tour offers a unique …More

Naples, USA

5.0 (5)

Guided Shelling Adventure in the Ten Thousand Islands

Discover the natural beauty of the Ten Thousand Islands on a guided shelling adventure led by Master Naturalist captains. This family-friendly tour offers a unique...

4 hours

5.0 (5)

from
$155

Fort lauderdale Christmas Holiday Lights Cruise

Don't miss Fort Lauderdale's best-priced holiday lights cruise! Step aboard our brand-new 65-foot Sea Rocket for 1 hour of pure holiday magic as you cruise …More

Fort Lauderdale, USA

4.5 (15)

Fort lauderdale Christmas Holiday Lights Cruise

Don't miss Fort Lauderdale's best-priced holiday lights cruise! Step aboard our brand-new 65-foot Sea Rocket for 1 hour of pure holiday magic as you cruise...

1 hour Free Cancellation

4.5 (15)

from
$33

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?