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) Nassau Swimming Pigs: Snorkeling, Lunch & Private Beach Club San Juan Sunset Harbor Boat Ride Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Full-Day Aruba History and Must-See Landmarks Tour 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) San Juan Sunset Harbor Boat Ride Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Full-Day Aruba History and Must-See Landmarks Tour Small-Group El Yunque Waterfall & Waterslides with Pickup 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 →

Congrats, you’ve just clicked on one of the top things to do in Curaçao! We're committed to giving you the most beautiful underwater tour and …More

4.9 (1,306)

Aquafari Tour in Curaçao

Congrats, you’ve just clicked on one of the top things to do in Curaçao! We're committed to giving you the most beautiful underwater tour and...

1 hour 15 minutes Free Cancellation

4.9 (1,306)

from
$159

San Juan Small Group Snorkeling Tour at Caribe Hilton

Jump in for a classic snorkeling experience from the Caribe Hilton hotel in San Juan. your friendly guides lead you along the rock reef in …More

5.0 (25)

San Juan Small Group Snorkeling Tour at Caribe Hilton

Jump in for a classic snorkeling experience from the Caribe Hilton hotel in San Juan. your friendly guides lead you along the rock reef in...

1 hour 30 minutes Free Cancellation

5.0 (25)

from
$77

Swim with Pigs & Beach Snorkeling with Turtle Viewing Rose Island

Explore the beauty of The Bahamas with a unique tour that features an encounter with the famous swimming pigs of Rose Island. Enjoy a scenic …More

4.4 (23)

Swim with Pigs & Beach Snorkeling with Turtle Viewing Rose Island

Explore the beauty of The Bahamas with a unique tour that features an encounter with the famous swimming pigs of Rose Island. Enjoy a scenic...

4 hours Free Cancellation

4.4 (23)

from
$99

Private Full Day Charter: St Lucia Boat Tour to Soufriere

Cruise down the beautiful west coast of St Lucia in a private speedboat to Soufriere and the Pitons on this full day tour. Choose between …More

Anse La Raye, St Lucia

5.0 (531)

Private Full Day Charter: St Lucia Boat Tour to Soufriere

Cruise down the beautiful west coast of St Lucia in a private speedboat to Soufriere and the Pitons on this full day tour. Choose between...

4 to 7 hours Hotel pickup offered Free Cancellation

5.0 (531)

from
$90

San Juan Bay Day Sail with Drinks Included

Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimosas, house rum punch, and other drinks in moderation (not a booze …More

5.0 (569)

San Juan Bay Day Sail with Drinks Included

Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimosas, house rum punch, and other drinks in moderation (not a booze...

1 hour 30 minutes Free Cancellation

5.0 (569)

from
$99

Yes! It's a real submarine. Take an exciting voyage to the depths of 130 feet below the Caribbean sea. Join Atlantis Submarines, voted Aruba's most …More

4.6 (1,197)

Aruba Atlantis Submarine Tour

Yes! It's a real submarine. Take an exciting voyage to the depths of 130 feet below the Caribbean sea. Join Atlantis Submarines, voted Aruba's most...

1 hour 45 minutes Free Cancellation

4.6 (1,197)

from
$151

Full-Day Cruise to Saona Island - Natural Pool and Lunch

already in bayahibe we boarded a motorboat, speedboat or catamaran. (If we go by boat we return by catamaran) (If we go by catamaran we …More

Punta Cana, Dominican Republic

4.1 (216)

Full-Day Cruise to Saona Island - Natural Pool and Lunch

already in bayahibe we boarded a motorboat, speedboat or catamaran. (If we go by boat we return by catamaran) (If we go by catamaran we...

10 hours 30 minutes Hotel pickup offered Free Cancellation

4.1 (216)

from
$75

Boat trip visit Mangroves, islets and lagoon

The lagoon of the Grand Cul de sac marin closed by the largest coral reef in the Lesser Antilles contains multiple biodiversity, mangroves, islands of …More

Basse-Terre Island, Guadeloupe

5.0 (691)

Boat trip visit Mangroves, islets and lagoon

The lagoon of the Grand Cul de sac marin closed by the largest coral reef in the Lesser Antilles contains multiple biodiversity, mangroves, islands of...

4 hours Free Cancellation

5.0 (691)

from
$68

When you book with us at Edmund Tours, you get value for your money. This tour allows you to discover and enjoy all the main …More

Marigot Bay, St Lucia

4.8 (1,994)

St. Lucia Land and Sea Tour

When you book with us at Edmund Tours, you get value for your money. This tour allows you to discover and enjoy all the main...

6 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (1,994)

from
$125

The Best Catamaran Day Sail in St Maarten (public, not private)

Sail in the Caribbean paradise of St Maarten on a casual yet upscale cruise within walking distance from the cruise ships and close to most …More

5.0 (1,805)

The Best Catamaran Day Sail in St Maarten (public, not private)

Sail in the Caribbean paradise of St Maarten on a casual yet upscale cruise within walking distance from the cruise ships and close to most...

5 hours Free Cancellation

5.0 (1,805)

from
$145

The Original Eco Tour Full-Day Around the Island of Sint Maarten

Enjoy a full day sailing aboard Too Rhum Punch or Quality Time our friendly comfortable and Fun Catamaran around the island of Sint Maarten / …More

4.9 (553)

The Original Eco Tour Full-Day Around the Island of Sint Maarten

Enjoy a full day sailing aboard Too Rhum Punch or Quality Time our friendly comfortable and Fun Catamaran around the island of Sint Maarten /...

8 hours Free Cancellation

4.9 (553)

from
$149

Two-in-One Day Trip: El Yunque and Bio Bay Tour with Transport

Get ready to experience two of Puerto Rico’s most amazing natural attractions in one unforgettable day! This full-day package covers the best of the East …More

Isla Verde, Puerto Rico

4.9 (1,432)

Two-in-One Day Trip: El Yunque and Bio Bay Tour with Transport

Get ready to experience two of Puerto Rico’s most amazing natural attractions in one unforgettable day! This full-day package covers the best of the East...

12 hours Hotel pickup offered Free Cancellation

4.9 (1,432)

from
$184

Bahamas Adventure: Pigs, Reef, Turtles, and Beach with Lunch

Hop aboard one of our luxury powerboats as we cruise to the cute and entertaining pigs of Rose Island! Get up close, take unforgettable selfies, …More

4.9 (730)

Bahamas Adventure: Pigs, Reef, Turtles, and Beach with Lunch

Hop aboard one of our luxury powerboats as we cruise to the cute and entertaining pigs of Rose Island! Get up close, take unforgettable selfies,...

4 hours Free Cancellation

4.9 (730)

from
$299

Best Luxury Catamaran Day Sail St Maarten on The Phoenix (Public)

Step aboard The Phoenix, a spacious sailing catamaran, and spend five unforgettable hours exploring the beautiful coastline of Sint Maarten. Relax on the sundeck with …More

4.9 (1,077)

Best Luxury Catamaran Day Sail St Maarten on The Phoenix (Public)

Step aboard The Phoenix, a spacious sailing catamaran, and spend five unforgettable hours exploring the beautiful coastline of Sint Maarten. Relax on the sundeck with...

5 hours Free Cancellation

4.9 (1,077)

from
$139

3 in 1 Full Day Cueva Ventana, Indian Cave & Waterfall Adventure

We want you to know every corner of Puerto Rico. For this reason, in this adventure, we will be visiting three different unique destinations on …More

5.0 (727)

3 in 1 Full Day Cueva Ventana, Indian Cave & Waterfall Adventure

We want you to know every corner of Puerto Rico. For this reason, in this adventure, we will be visiting three different unique destinations on...

9 to 10 hours Hotel pickup offered Free Cancellation

5.0 (727)

from
$155

Horseback Ride Tour to Natural Pool in Arikok National Park

Get back to nature with Rancho Loco on the one and only horseback riding tour through Arikok National Park to the Natural Pool, Aruba’s most …More

Palm - Eagle Beach, Aruba

4.9 (1,251)

Horseback Ride Tour to Natural Pool in Arikok National Park

Get back to nature with Rancho Loco on the one and only horseback riding tour through Arikok National Park to the Natural Pool, Aruba’s most...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (1,251)

from
$155

Stingray City Experience Plus Two Snorkeling Stops on Grand Cayman

This tour goes to the Stingray City sandbar where you will interact with stingrays. This tour also includes two snorkeling stops, the magnificent Coral Gardens …More

Seven Mile Beach, Cayman Islands

4.9 (1,595)

Stingray City Experience Plus Two Snorkeling Stops on Grand Cayman

This tour goes to the Stingray City sandbar where you will interact with stingrays. This tour also includes two snorkeling stops, the magnificent Coral Gardens...

3 hours Hotel pickup offered Free Cancellation

4.9 (1,595)

from
$80

Come experience a great atmosphere with a personal touch on this full day excursion to explore to beautiful island of Anguilla. Snorkel with tropical fish and turtles, enjoy …More

4.9 (754)

Anguilla Getaway Cruise

Come experience a great atmosphere with a personal touch on this full day excursion to explore to beautiful island of Anguilla. Snorkel with tropical fish and turtles, enjoy...

7 hours Free Cancellation

4.9 (754)

from
$149

Day trip at sea to the Fonds Blancs Martinique Windward Coast

The most popular walk in Martinique with a small group program to discover and rediscover the beauty of the Atlantic coast. Many legends and explanations …More

4.8 (40)

Day trip at sea to the Fonds Blancs Martinique Windward Coast

The most popular walk in Martinique with a small group program to discover and rediscover the beauty of the Atlantic coast. Many legends and explanations...

7 hours Free Cancellation

4.8 (40)

from
$97

All-Inclusive Private Charter to Icacos or Palomino Islands

Escape to Paradise PR offers you a once in a life time experience. Our tours are personalized. We only take you and your group in …More

Fajardo, Puerto Rico

5.0 (503)

All-Inclusive Private Charter to Icacos or Palomino Islands

Escape to Paradise PR offers you a once in a life time experience. Our tours are personalized. We only take you and your group in...

4 hours Free Cancellation

5.0 (503)

from
$750

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?