Top Caribbean Cruises, Sailing & Water Tours

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

Caribbean Cruises, Sailing & Water Tours with Instant Confirmation include: 2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only) San Juan Sunset Harbor Boat Ride Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Full-Day Aruba History and Must-See Landmarks Tour Nassau Swimming Pigs: Snorkeling, Lunch & Private Beach Club View all Tours with Instant Confirmation →

Q: I need a ride! Which Caribbean Cruises, Sailing & Water Tours have Hotel Pickup?

No problem. These Caribbean Cruises, Sailing & Water Tours include Hotel Pickup: 2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only) Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Full-Day Aruba History and Must-See Landmarks Tour Small-Group El Yunque Waterfall & Waterslides with Pickup Aruba North Coast ATV Desert Adventure View all Tours with Hotel Pickup →

Q: Got any more Caribbean trip ideas?

We sure do. Check out our curated lists of hand-picked Caribbean Tours. Top 10 Caribbean 2026 Senior-friendly tours Caribbean The best tours and activities for culture lovers in Caribbean Top Day Trips from Caribbean Things to do in Caribbean this summer View all Caribbean Trip Ideas →

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

Based on our sales data over the past year, the most popular styles of tours and activities in Caribbean are: Caribbean Luxury & Special Occasions Caribbean Luxury Tours Caribbean Tours & Sightseeing Caribbean Shore Excursions Caribbean Port Transfers View all tour styles in Caribbean →

Half Day Big Game Fishing private charter

1/2 DAY BIG GAME FISHING All hours available, we pick you up any time! Location: Puerto Plata - Sosua - Cabarete - Amber Cove All excursions …More

Puerto Plata, Dominican Republic

4.9 (17)

Half Day Big Game Fishing private charter

1/2 DAY BIG GAME FISHING All hours available, we pick you up any time! Location: Puerto Plata - Sosua - Cabarete - Amber Cove All excursions...

4 hours Hotel pickup offered Free Cancellation

4.9 (17)

from
$490

The sail with us for the ultimate Puerto Rican boat experience! Whether you’re looking to make new friends at our lively Mix & Mingle boat …More

Fajardo, Puerto Rico

5.0 (21)

Private Boat Trip to Icacos & Palomino

The sail with us for the ultimate Puerto Rican boat experience! Whether you’re looking to make new friends at our lively Mix & Mingle boat...

4 hours Free Cancellation

5.0 (21)

from
$1,300

2 Hour Private Sunset Catamaran Sailing Charter from Grace Bay, Providenciales

There’s no better way to soak up the last rays of the Caribbean sun than with a Private Champagne Sail in Turks and Caicos. Get picked …More

5.0 (9)

2 Hour Private Sunset Catamaran Sailing Charter from Grace Bay, Providenciales

There’s no better way to soak up the last rays of the Caribbean sun than with a Private Champagne Sail in Turks and Caicos. Get picked...

2 hours Free Cancellation

5.0 (9)

from
$2,100

Private Sunset Dinner Cruise in Bonaire w/ Sailing & Snorkeling

This private tour has it all! Sailing, snorkeling, sunset dinner cruise, and star-gazing. Our 4.5 hour tour starts at 3:00 p.m. and ends at 7:30 …More

5.0 (22)

Private Sunset Dinner Cruise in Bonaire w/ Sailing & Snorkeling

This private tour has it all! Sailing, snorkeling, sunset dinner cruise, and star-gazing. Our 4.5 hour tour starts at 3:00 p.m. and ends at 7:30...

4 hours 30 minutes

5.0 (22)

from
$2,499

VIP tour to Paradise Island & The Mangroves

The VIP tour to Paradise Island starts early in the morning because we like to get to the island before all the other tourists arrives. …More

Cabarete, Dominican Republic

4.8 (8)

VIP tour to Paradise Island & The Mangroves

The VIP tour to Paradise Island starts early in the morning because we like to get to the island before all the other tourists arrives....

11 hours Hotel pickup offered Free Cancellation

4.8 (8)

from
$159

Private Full-Day Tour to Saona Island from Bayahibe with Lunch

Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve) it’s a …More

Punta Cana, Dominican Republic

5.0 (1)

Private Full-Day Tour to Saona Island from Bayahibe with Lunch

Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve) it’s a...

8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$2,300

Full-day Buggy & Party Boat tour: snorkel, open bar, cave pool

This great adventure divided into 2 excursions will make you live a wonderful experience accompanied by our incredible staff. you will discover the Dominican countryside. …More

Punta Cana, Dominican Republic

4.8 (33)

Full-day Buggy & Party Boat tour: snorkel, open bar, cave pool

This great adventure divided into 2 excursions will make you live a wonderful experience accompanied by our incredible staff. you will discover the Dominican countryside....

8 hours Hotel pickup offered Free Cancellation

4.8 (33)

from
$105

Full-Day Tour to Punta Rucia and Cayo Arena with Snorkeling

Visit one of the most beautiful islands on the North Coast. Paradise Island will welcome you with turquoise water, white sand and colorful reef. Visit …More

Cabarete, Dominican Republic

4.0 (20)

Full-Day Tour to Punta Rucia and Cayo Arena with Snorkeling

Visit one of the most beautiful islands on the North Coast. Paradise Island will welcome you with turquoise water, white sand and colorful reef. Visit...

9 to 11 hours Free Cancellation

4.0 (20)

from
$89

Fajardo: Full-Day Private Fishing Charter with Snorkeling, Beach

This Inshore Fishing Trip is designed by Pure Adventure’s Marine Biologist and fishing experts to ensure a sure catch in a short period, so everybody …More

Fajardo, Puerto Rico

5.0 (3)

Fajardo: Full-Day Private Fishing Charter with Snorkeling, Beach

This Inshore Fishing Trip is designed by Pure Adventure’s Marine Biologist and fishing experts to ensure a sure catch in a short period, so everybody...

7 hours Free Cancellation

5.0 (3)

from
$1,400

Guided boat tour to your choice of the following stops: • Stingray Sand Bar • Starfish Beach • Coral Gardens • Barrier Reef • Kaibo …More

Grand Cayman, Cayman Islands

5.0 (21)

Party Boat Cruise

Guided boat tour to your choice of the following stops: • Stingray Sand Bar • Starfish Beach • Coral Gardens • Barrier Reef • Kaibo...

4 hours Free Cancellation

5.0 (21)

from
$1,050

Charter our boat is a private power boat charter.

We are a private power boat tour, that services all you need's . Take's you to all different stops to snorkel. Different beaches around the …More

5.0 (32)

Charter our boat is a private power boat charter.

We are a private power boat tour, that services all you need's . Take's you to all different stops to snorkel. Different beaches around the...

7 hours Free Cancellation

5.0 (32)

from
$1,100

Rodney Bay to Soufriere Catamaran Transfer

Join us on a one-way water transfer from Rodney Bay to Soufriere and experience Saint Lucia from the water. For your convenience, Sea Spray Cruises …More

Choc, St Lucia

4.9 (8)

Rodney Bay to Soufriere Catamaran Transfer

Join us on a one-way water transfer from Rodney Bay to Soufriere and experience Saint Lucia from the water. For your convenience, Sea Spray Cruises...

2 hours Free Cancellation

4.9 (8)

from
$55

Soufriere Excursion with Rum & Chocolate Tasting

This tour offers travelers the chance to see all of St. Lucia's great sites in one day while also giving them the chance to sample …More

Choc, St Lucia

4.6 (12)

Soufriere Excursion with Rum & Chocolate Tasting

This tour offers travelers the chance to see all of St. Lucia's great sites in one day while also giving them the chance to sample...

8 hours 30 minutes Free Cancellation

4.6 (12)

from
$195

USDA El Yunque National Forest and Luquillo Beach Tour

El Yunque National Forest Adventure: Discover, Delight, Dive! Unveil Nature's Treasure: Embark on an exploration of the USDA National Forest of El Yunque. Encounter the …More

Luquillo, Puerto Rico

4.8 (12)

USDA El Yunque National Forest and Luquillo Beach Tour

El Yunque National Forest Adventure: Discover, Delight, Dive! Unveil Nature's Treasure: Embark on an exploration of the USDA National Forest of El Yunque. Encounter the...

6 hours Hotel pickup offered Free Cancellation

4.8 (12)

from
$79

Stingray City, Coral Gardens & Frankie's Local Lunch & Juice

Friendly, responsible, and courteous staff that guides and informs our clients of all courtesies available to them. This would include free on-board refreshments, very tentative …More

Seven Mile Beach, Cayman Islands

4.8 (6)

Stingray City, Coral Gardens & Frankie's Local Lunch & Juice

Friendly, responsible, and courteous staff that guides and informs our clients of all courtesies available to them. This would include free on-board refreshments, very tentative...

4 hours Hotel pickup offered Free Cancellation

4.8 (6)

from
$68

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands. Looking for more time …More

5.0 (32)

Group Sunset Sail St. John

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands. Looking for more time...

2 hours 30 minutes Free Cancellation

5.0 (32)

from
$245

All-Inclusive Guided Tour to Saona Islands from Punta Cana

Embark on an unforgettable excursion to Saône Island, a tropical paradise in the Caribbean. Enjoy white sandy beaches, crystal clear waters and a relaxing atmosphere. …More

Punta Cana, Dominican Republic

4.9 (13)

All-Inclusive Guided Tour to Saona Islands from Punta Cana

Embark on an unforgettable excursion to Saône Island, a tropical paradise in the Caribbean. Enjoy white sandy beaches, crystal clear waters and a relaxing atmosphere....

8 hours Hotel pickup offered Free Cancellation

4.9 (13)

from
$78

Piton Sunset Snorkel Cruise St. Lucia From Castries

Enjoy a catamaran cruise to the majestic Pitons, swim and snorkel over protected reefs near the Pitons. Cruise up the coast to Marigot Bay, enjoy the …More

Choc, St Lucia

4.3 (57)

Piton Sunset Snorkel Cruise St. Lucia From Castries

Enjoy a catamaran cruise to the majestic Pitons, swim and snorkel over protected reefs near the Pitons. Cruise up the coast to Marigot Bay, enjoy the...

5 hours Hotel pickup offered

4.3 (57)

from
$111

4HR Private bottom Fishing Charter with lunch

Your guaranteed a memorable Luxury sea adventure, to our charters we add quality and numerous activities, your family will enjoy it, our super experienced and …More

4.9 (33)

4HR Private bottom Fishing Charter with lunch

Your guaranteed a memorable Luxury sea adventure, to our charters we add quality and numerous activities, your family will enjoy it, our super experienced and...

4 hours Hotel pickup offered Free Cancellation

4.9 (33)

from
$1,590

Saona Island Day Trip with Lunch, Transportation and Drinks

Just imagine the scenery: beaches with turquoise waters, wild vegetation everywhere, giant starfish, sea turtles, golden sand, coral reefs and a festive atmosphere. This and …More

3.7 (14)

Saona Island Day Trip with Lunch, Transportation and Drinks

Just imagine the scenery: beaches with turquoise waters, wild vegetation everywhere, giant starfish, sea turtles, golden sand, coral reefs and a festive atmosphere. This and...

8 hours 10 minutes Hotel pickup offered Free Cancellation

3.7 (14)

from
$55

Frequently Asked Questions

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

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

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

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

View all kid-friendly Tours →

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

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

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

Got any more Caribbean trip ideas?

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