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 →

Build Your Private Charter: Snorkel, Stingrays, or Bio

**Accommodates up to 7 Passengers** Personalized Experience: Our small group sizes ensure a more intimate and personalized experience. You’ll have plenty of opportunities to ask …More

Grand Cayman, Cayman Islands

5.0 (41)

Build Your Private Charter: Snorkel, Stingrays, or Bio

**Accommodates up to 7 Passengers** Personalized Experience: Our small group sizes ensure a more intimate and personalized experience. You’ll have plenty of opportunities to ask...

2 to 4 hours Free Cancellation

5.0 (41)

from
$500

Bamboo River Rafting Limestone Foot Massage in Montego Bay Ja.

Simpson Tours Jamaica provides exceptional private taxi service to travelers in Jamaica. bamboo rafting is a popular outdoor activity where people ride on boats made …More

Montego Bay, Jamaica

4.9 (51)

Bamboo River Rafting Limestone Foot Massage in Montego Bay Ja.

Simpson Tours Jamaica provides exceptional private taxi service to travelers in Jamaica. bamboo rafting is a popular outdoor activity where people ride on boats made...

1 to 2 hours Hotel pickup offered Free Cancellation

4.9 (51)

from
$120

Puerto Plata Private Boat Cruise with Snorkeling and Open Bar

Ready to make your Caribbean adventure unforgettable? Whether you're arriving on a cruise or staying at a hotel in Puerto Plata, this private boat adventure …More

Puerto Plata, Dominican Republic

4.6 (31)

Puerto Plata Private Boat Cruise with Snorkeling and Open Bar

Ready to make your Caribbean adventure unforgettable? Whether you're arriving on a cruise or staying at a hotel in Puerto Plata, this private boat adventure...

4 hours Hotel pickup offered Free Cancellation

4.6 (31)

from
$109

Private Yacht for Excursions in Punta Cana, Snorkeling and Booze

The yatch comes equipped with air conditioner, plasma TV, bathroom, full kitchen, amazing stereo system, wifi, king size bed, two couches, snorkeling equipment, two paddle …More

5.0 (26)

Private Yacht for Excursions in Punta Cana, Snorkeling and Booze

The yatch comes equipped with air conditioner, plasma TV, bathroom, full kitchen, amazing stereo system, wifi, king size bed, two couches, snorkeling equipment, two paddle...

3 hours Hotel pickup offered Free Cancellation

5.0 (26)

from
$1,350

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea ending in an amazing sunset setting. …More

Fajardo, Puerto Rico

4.9 (21)

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea ending in an amazing sunset setting....

3 hours Free Cancellation

4.9 (21)

from
$229

St.Kitts Water Sports is thrilled to bring you yet another unforgettable experience. Experience the sensation of flight with our newest activity… parasailing! Get towed up …More

4.9 (56)

Parasailing Adventure

St.Kitts Water Sports is thrilled to bring you yet another unforgettable experience. Experience the sensation of flight with our newest activity… parasailing! Get towed up...

60 to 90 minutes Free Cancellation

4.9 (56)

from
$130

Grand Cayman Catamaran Tour to Stingray City and Rum Point

Visit two of Grand Cayman’s top attractions — Stingray City and Rum Point — on this 5.5-hour tour by luxury 65-foot (20-meter) catamaran. Accessible only …More

Seven Mile Beach, Cayman Islands

4.8 (39)

Grand Cayman Catamaran Tour to Stingray City and Rum Point

Visit two of Grand Cayman’s top attractions — Stingray City and Rum Point — on this 5.5-hour tour by luxury 65-foot (20-meter) catamaran. Accessible only...

5 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (39)

from
$144

Take a relaxing cruise along the picturesque shores of Seven Mile Beach and enjoy some of the best snorkeling on Grand Cayman! Visit both a …More

Grand Cayman, Cayman Islands

4.5 (32)

Grand Cayman Kittiwake and Reef Sail

Take a relaxing cruise along the picturesque shores of Seven Mile Beach and enjoy some of the best snorkeling on Grand Cayman! Visit both a...

2 hours 30 minutes Free Cancellation

4.5 (32)

from
$124

Full Day Private Boat Charter at Grace Bay, Providenciales

Cruise around the islands of Turks and Caicos in style! Charter a private boat up to 8 people ($99 for each additional person after 8 …More

5.0 (26)

Full Day Private Boat Charter at Grace Bay, Providenciales

Cruise around the islands of Turks and Caicos in style! Charter a private boat up to 8 people ($99 for each additional person after 8...

8 hours Hotel pickup offered Free Cancellation

5.0 (26)

from
$3,540

Cueva del Indio and Charco Azul Cave and Waterfall Adventure

This is the best adventure tour in all Puerto Rico as it completely avoids the tourist traps of the island & focuses exclusively on amazing …More

Arecibo, Puerto Rico

4.9 (43)

Cueva del Indio and Charco Azul Cave and Waterfall Adventure

This is the best adventure tour in all Puerto Rico as it completely avoids the tourist traps of the island & focuses exclusively on amazing...

8 hours Free Cancellation

4.9 (43)

from
$175

Come aboard the comfortable Janise Lagoon 380 for a memorable 8-hourfull day charter in the beautiful Spanish Virgin Islands. Come experience first class service by …More

Fajardo, Puerto Rico

5.0 (16)

Private Janise Sailing Full Day Charter in Fajardo, Puerto Rico

Come aboard the comfortable Janise Lagoon 380 for a memorable 8-hourfull day charter in the beautiful Spanish Virgin Islands. Come experience first class service by...

8 hours Free Cancellation

5.0 (16)

from
$2,395

Private Saona Island Boat Tour | No Crowds | From 165 USD pp

We do things differently. Our team blends American attitude, German efficiency, and Dominican flow to create a smooth, personal experience from start to finish. No …More

La Romana, Dominican Republic

4.9 (43)

Private Saona Island Boat Tour | No Crowds | From 165 USD pp

We do things differently. Our team blends American attitude, German efficiency, and Dominican flow to create a smooth, personal experience from start to finish. No...

6 to 8 hours Hotel pickup offered Free Cancellation

4.9 (43)

from
$165

An unforgettable experience in the very heart of one of the jewels of Martinique. You will be guided between the white bottoms with crystal clear …More

5.0 (15)

Half-day boat trip from Le Robert

An unforgettable experience in the very heart of one of the jewels of Martinique. You will be guided between the white bottoms with crystal clear...

4 hours Free Cancellation

5.0 (15)

from
$65

Turks and Caicos Full-Day Luxury Private Yacht Charter

Make your dream come through with a day out on the beautiful islands and beaches of the Turks and Caicos. Your luxury boat tour on …More

5.0 (37)

Turks and Caicos Full-Day Luxury Private Yacht Charter

Make your dream come through with a day out on the beautiful islands and beaches of the Turks and Caicos. Your luxury boat tour on...

7 hours Free Cancellation

5.0 (37)

from
$7,400

Nassau: Bahamas Swimming Pigs & Pearl Island Beach with Lunch

You've seen the swimming pigs all over your feed — now it's your turn, and a full island day comes with them. From Nassau, head …More

4.2 (132)

Nassau: Bahamas Swimming Pigs & Pearl Island Beach with Lunch

You've seen the swimming pigs all over your feed — now it's your turn, and a full island day comes with them. From Nassau, head...

5 hours Free Cancellation

4.2 (132)

from
$168

Create-Your-Own Luxury Adventure in Nassau with photographer

Embrace the crystal‑clear turquoise waters of Nassau on our private adventure. Designed for travelers who want freedom, fun, and unforgettable island vibes. Choose your stops, …More

Nassau, Bahamas

4.9 (29)

Create-Your-Own Luxury Adventure in Nassau with photographer

Embrace the crystal‑clear turquoise waters of Nassau on our private adventure. Designed for travelers who want freedom, fun, and unforgettable island vibes. Choose your stops,...

4 hours Hotel pickup offered Free Cancellation

4.9 (29)

from
$1,600

What makes this product unique is that you will spend day on the water, your way, and your rules. With the Cocktails N’ Dreams private …More

4.7 (25)

All Inclusive 4- Hours Private Charter

What makes this product unique is that you will spend day on the water, your way, and your rules. With the Cocktails N’ Dreams private...

4 hours Hotel pickup offered Free Cancellation

4.7 (25)

from
$1,600

St. Thomas Dinner Sail to St. John with Open Bar - Ritz-Carlton

Step aboard our luxury 53 foot catamaran for an evening escape to the island of St. John. This popular sail departs directly from The Ritz-Carlton …More

4.7 (56)

St. Thomas Dinner Sail to St. John with Open Bar - Ritz-Carlton

Step aboard our luxury 53 foot catamaran for an evening escape to the island of St. John. This popular sail departs directly from The Ritz-Carlton...

5 hours Free Cancellation

4.7 (56)

from
$149

Private Full Day BVI Boat Charter Aboard MV Aquarius

Your group will spend the day enjoying the many isles and harbors of the U.S and BVIs on your own private powerboat. MV Aquarius is …More

5.0 (30)

Private Full Day BVI Boat Charter Aboard MV Aquarius

Your group will spend the day enjoying the many isles and harbors of the U.S and BVIs on your own private powerboat. MV Aquarius is...

8 hours Free Cancellation

5.0 (30)

from
$2,295

Pigs Beach, Green Turtle Cay, Rose Island Private Tour

From the moment you are picked up from the dock. The captain ensures that everyone on board is safely seated and informed of the safety …More

4.8 (22)

Pigs Beach, Green Turtle Cay, Rose Island Private Tour

From the moment you are picked up from the dock. The captain ensures that everyone on board is safely seated and informed of the safety...

3 hours 30 minutes Free Cancellation

4.8 (22)

from
$1,200

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?

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

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?