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 →

Grab the wheel of your own 17 ft. speedboat as you cruise along the picturesque vistas of St. Lucia and into an enchanting snorkeling experience. …More

Rodney Bay, St Lucia

4.9 (27)

St. Lucia Drive and Snorkel Experience

Grab the wheel of your own 17 ft. speedboat as you cruise along the picturesque vistas of St. Lucia and into an enchanting snorkeling experience....

2 hours Hotel pickup offered

4.9 (27)

from
$226

Step aboard our 35’ Donzi center console for a private Cayman Islands adventure built entirely around you. A spacious layout, premium sound system, comfortable seating, …More

Grand Cayman, Cayman Islands

4.9 (26)

Private Boat Charter in Cayman Islands

Step aboard our 35’ Donzi center console for a private Cayman Islands adventure built entirely around you. A spacious layout, premium sound system, comfortable seating,...

3 hours Free Cancellation

4.9 (26)

from
$900

This is not just a fishing trip — it’s a complete deep-sea fishing experience designed for comfort, excitement, and great results. From hotel pickup to …More

Punta Cana, Dominican Republic

4.4 (28)

4 Hour Punta Cana Fishing Tour

This is not just a fishing trip — it’s a complete deep-sea fishing experience designed for comfort, excitement, and great results. From hotel pickup to...

4 hours Hotel pickup offered Free Cancellation

4.4 (28)

from
$97

Scuba Dive and Snorkel Private Charter in Puerto Rico

Because SCUBA diving and snorkeling in a natural aquarium is possible! If there is a certified diver in your party, we can easily arrange a …More

5.0 (3)

Scuba Dive and Snorkel Private Charter in Puerto Rico

Because SCUBA diving and snorkeling in a natural aquarium is possible! If there is a certified diver in your party, we can easily arrange a...

4 hours Free Cancellation

5.0 (3)

from
$1,500

Shore Excursion Explore & Discover Barbados Land & Sea Tour

Explore the beauty, history, and culture of Barbados on a wonderful island adventure. Begin by visiting the street where international superstar Rihanna once lived and …More

4.7 (7)

Shore Excursion Explore & Discover Barbados Land & Sea Tour

Explore the beauty, history, and culture of Barbados on a wonderful island adventure. Begin by visiting the street where international superstar Rihanna once lived and...

6 hours Free Cancellation

4.7 (7)

from
$97

Tiki Pon Da Sea Cruise to Booby Cay with Lunch from Negril

Plan a cruise to the Booby Cay Island from the 7 mile beach in Negril and relax on the sea then experience a taste of …More

Negril, Jamaica

4.8 (10)

Tiki Pon Da Sea Cruise to Booby Cay with Lunch from Negril

Plan a cruise to the Booby Cay Island from the 7 mile beach in Negril and relax on the sea then experience a taste of...

3 hours Hotel pickup offered Free Cancellation

4.8 (10)

from
$235

Private Speedboat Charter: St Maarten to Anguilla

Discover Anguilla on a private speedboat charter from St Maarten! Visit the best snorkeling sites, stop at some of the most pristine islands or beach …More

5.0 (8)

Private Speedboat Charter: St Maarten to Anguilla

Discover Anguilla on a private speedboat charter from St Maarten! Visit the best snorkeling sites, stop at some of the most pristine islands or beach...

7 hours Free Cancellation

5.0 (8)

from
$1,500

Ultimate Private Tour Around Tortola in British Virgin Islands

Antilles Power Boats will ensure that you have the most memorable day with us . The boat, NautiGal, is custom designed to carry up to …More

Tortola, British Virgin Islands

5.0 (5)

Ultimate Private Tour Around Tortola in British Virgin Islands

Antilles Power Boats will ensure that you have the most memorable day with us . The boat, NautiGal, is custom designed to carry up to...

7 hours Free Cancellation

5.0 (5)

from
$1,950

Guided boat and bus tours to the islands best attractions: • Stingray Sand Bar • Starfish Beach • Coral Gardens • Barrier Reef • Kaibo …More

Grand Cayman, Cayman Islands

4.9 (29)

Get Anchored

Guided boat and bus tours to the islands best attractions: • Stingray Sand Bar • Starfish Beach • Coral Gardens • Barrier Reef • Kaibo...

2 to 5 hours Hotel pickup offered Free Cancellation

4.9 (29)

from
$800

Saona Island Full-Day Tour with Lunch from Punta Cana

Pure relaxation awaits on this full day cruise to Saona Island from Bayahibe. Saona Island is all swaying palm trees, white soft sands and crystal …More

Puerto Plata, Dominican Republic

4.0 (41)

Saona Island Full-Day Tour with Lunch from Punta Cana

Pure relaxation awaits on this full day cruise to Saona Island from Bayahibe. Saona Island is all swaying palm trees, white soft sands and crystal...

8 hours Hotel pickup offered Free Cancellation

4.0 (41)

from
$90

Punta Cana Small-Group Cruise With Snorkeling and Seafood Lunch

Sharky Catamarans are the kings of the Caribbean when it comes to cruises. When you're not enjoying the atmosphere on board, you'll be snorkelling in …More

Punta Cana, Dominican Republic

4.9 (12)

Punta Cana Small-Group Cruise With Snorkeling and Seafood Lunch

Sharky Catamarans are the kings of the Caribbean when it comes to cruises. When you're not enjoying the atmosphere on board, you'll be snorkelling in...

4 hours Hotel pickup offered Free Cancellation

4.9 (12)

from
$114

Cayman Combo Tour: Stingrays, Starfish Point and Crystal Caves

Embark on an unforgettable journey through three of Grand Cayman’s natural wonders! Begin at Stingray City, where you’ll stand in crystal-clear Caribbean waters as graceful …More

Grand Cayman, Cayman Islands

4.7 (21)

Cayman Combo Tour: Stingrays, Starfish Point and Crystal Caves

Embark on an unforgettable journey through three of Grand Cayman’s natural wonders! Begin at Stingray City, where you’ll stand in crystal-clear Caribbean waters as graceful...

3 to 330 minutes Hotel pickup offered Free Cancellation

4.7 (21)

from
$109

Partez pour un moment de détente et de découverte de la Côte Sud Caraïbe de la Martinique. Allez à la rencontre de la nature, de …More

4.0 (48)

Martinique : Anse Coralienne & Tortues

Partez pour un moment de détente et de découverte de la Côte Sud Caraïbe de la Martinique. Allez à la rencontre de la nature, de...

4 hours Free Cancellation

4.0 (48)

from
$85

CaptainManou offers rides in small groups, away from the crowd and other boats (10 passengers max) and off traditional circuits. Sailor-fisherman by profession, he will …More

5.0 (20)

Captainmanou water excursions

CaptainManou offers rides in small groups, away from the crowd and other boats (10 passengers max) and off traditional circuits. Sailor-fisherman by profession, he will...

8 hours Free Cancellation

5.0 (20)

from
$115

Puerto Plata Party Boat Cruise with Snorkeling and Open Bar

Looking for the highlight of your day in Puerto Plata? This shared party boat experience takes you to Sosúa, one of the Dominican Republic’s most …More

Puerto Plata, Dominican Republic

4.4 (22)

Puerto Plata Party Boat Cruise with Snorkeling and Open Bar

Looking for the highlight of your day in Puerto Plata? This shared party boat experience takes you to Sosúa, one of the Dominican Republic’s most...

4 hours Hotel pickup offered Free Cancellation

4.4 (22)

from
$89

Spend a leisurely afternoon aboard a catamaran on this 2.5-hour snorkel and party cruise. Depart from the swanky marina of Cap Cana, one of the …More

Punta Cana, Dominican Republic

4.2 (19)

Scape Park Sunshine Cruise at Cap Cana

Spend a leisurely afternoon aboard a catamaran on this 2.5-hour snorkel and party cruise. Depart from the swanky marina of Cap Cana, one of the...

2 hours 30 minutes Hotel pickup offered Free Cancellation

4.2 (19)

from
$89

Fun Fishing Tour (Snacks & Light Refreshments Offered)

Enjoy the best fishing in the Caribbeans with our experienced staff. If you want to experience a great saltwater adventure, in a part of the …More

5.0 (29)

Fun Fishing Tour (Snacks & Light Refreshments Offered)

Enjoy the best fishing in the Caribbeans with our experienced staff. If you want to experience a great saltwater adventure, in a part of the...

3 hours 30 minutes

5.0 (29)

from
$150

Two Hours of Sailing and Relaxation in the Bay of Saintes

In an intimate setting (max 7 people), come and discover the Saintes archipelago by sail! I'll take you to Terre de Bas to observe the …More

4.9 (11)

Two Hours of Sailing and Relaxation in the Bay of Saintes

In an intimate setting (max 7 people), come and discover the Saintes archipelago by sail! I'll take you to Terre de Bas to observe the...

2 hours Free Cancellation

4.9 (11)

from
$63

Private All-Inclusive Sea and Land Tour in St Lucia

Explore St. Lucia's highlights through a guided half-day tour by sea and land. Begin your journey cruising along the island's stunning coastline en route to …More

Rodney Bay, St Lucia

5.0 (12)

Private All-Inclusive Sea and Land Tour in St Lucia

Explore St. Lucia's highlights through a guided half-day tour by sea and land. Begin your journey cruising along the island's stunning coastline en route to...

5 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$140

Embark on an unforgettable adventure as you kayak through our enchanting mangrove lagoon, leading to a stunning secluded beach. Experience a short boat ride to …More

5.0 (13)

SoCoHo Eco Kayak and Snorkel Tour

Embark on an unforgettable adventure as you kayak through our enchanting mangrove lagoon, leading to a stunning secluded beach. Experience a short boat ride to...

3 hours Free Cancellation

5.0 (13)

from
$88

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?