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 →

Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx

Introducing the newest luxury pontoon boat experience in Barbados — complete with an upper-level deck that offers stunning panoramic views of the ocean and unforgettable …More

4.9 (79)

Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx

Introducing the newest luxury pontoon boat experience in Barbados — complete with an upper-level deck that offers stunning panoramic views of the ocean and unforgettable...

3 hours Free Cancellation

4.9 (79)

from
$105

Half-Day El Yunque Rainforest Wilderness Adventure

Take the time to escape to heaven on Earth. Adventure calls you and it's time to respond to that call of life to break the routine, …More

Fajardo, Puerto Rico

5.0 (140)

Half-Day El Yunque Rainforest Wilderness Adventure

Take the time to escape to heaven on Earth. Adventure calls you and it's time to respond to that call of life to break the routine,...

4 hours Free Cancellation

5.0 (140)

from
$179

4 Hour British Virgin Islands Full Private Experience

Lets take you on a journey that unveils the mysteries of nature's little secret. Traverse the unbeaten paths, experience our local dishes, swim in our …More

Tortola, British Virgin Islands

4.9 (39)

4 Hour British Virgin Islands Full Private Experience

Lets take you on a journey that unveils the mysteries of nature's little secret. Traverse the unbeaten paths, experience our local dishes, swim in our...

4 hours Free Cancellation

4.9 (39)

from
$220

What really makes our tour special is the unique mix of exclusive experiences we have organized to ensure you have an unforgettable adventure at sea. …More

5.0 (24)

Private Boat Party in Punta Cana

What really makes our tour special is the unique mix of exclusive experiences we have organized to ensure you have an unforgettable adventure at sea....

3 hours Hotel pickup offered Free Cancellation

5.0 (24)

from
$70

Grand Cayman: Stingray City, Starfish Point & Crystal Caves

From Caribbean waters to Grand Cayman’s hidden world underground, experience completely different sides of the island in one unforgettable day. Step into the shallow waters …More

Grand Cayman, Cayman Islands

4.8 (20)

Grand Cayman: Stingray City, Starfish Point & Crystal Caves

From Caribbean waters to Grand Cayman’s hidden world underground, experience completely different sides of the island in one unforgettable day. Step into the shallow waters...

90 to 330 minutes Hotel pickup offered Free Cancellation

4.8 (20)

from
$95

Bamboo River Rafting Experience with Limestone Foot Massage

Located in the hills of Hanover Lethe is the perfect combination of land and water with picturesque views from the hills to the tranquility of …More

Trelawny, Jamaica

5.0 (38)

Bamboo River Rafting Experience with Limestone Foot Massage

Located in the hills of Hanover Lethe is the perfect combination of land and water with picturesque views from the hills to the tranquility of...

2 hours Hotel pickup offered Free Cancellation

5.0 (38)

from
$100

Private Bamboo Rafting Tour with Leg Massage and Hip-Strip

Private transportation for you and your group only without the hassle of multiple stops along the way to pickup others that you do not know. …More

Montego Bay, Jamaica

4.9 (30)

Private Bamboo Rafting Tour with Leg Massage and Hip-Strip

Private transportation for you and your group only without the hassle of multiple stops along the way to pickup others that you do not know....

5 hours Hotel pickup offered Free Cancellation

4.9 (30)

from
$120

ATV and Jet Ski Options in Montego Bay with Transportation

Enjoy a Combination of water Jet Skis and off-road ATV ride or each activity by itself on this private experience. We will pick you up …More

Montego Bay, Jamaica

4.5 (32)

ATV and Jet Ski Options in Montego Bay with Transportation

Enjoy a Combination of water Jet Skis and off-road ATV ride or each activity by itself on this private experience. We will pick you up...

2 to 3 hours Hotel pickup offered Free Cancellation

4.5 (32)

from
$129

Private Day Sail - South Coast of Puerto Rico

Our experienced USCG Captain and crew will make sure you experience the most beautiful and secluded spots of the Jobos Bay National Estuarine Research Reserve …More

4.9 (23)

Private Day Sail - South Coast of Puerto Rico

Our experienced USCG Captain and crew will make sure you experience the most beautiful and secluded spots of the Jobos Bay National Estuarine Research Reserve...

6 hours Free Cancellation

4.9 (23)

from
$680

VIP Private Booze Cruise with Live Dj and BBQ in Punta Cana

Explore the beauty of the shores of Punta Cana, and get the best experience of your vacation, follow our animation team to enjoy dancing to …More

Punta Cana, Dominican Republic

5.0 (39)

VIP Private Booze Cruise with Live Dj and BBQ in Punta Cana

Explore the beauty of the shores of Punta Cana, and get the best experience of your vacation, follow our animation team to enjoy dancing to...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (39)

from
$148

ATV, Bamboo Rafting, and Horseback Ride Tour From Montego Bay

3 thrilling activities, 2 unforgettable cities! Discover the ultimate Jamaican adventure with our ATV, Bamboo Rafting, and Horseback Riding combo tour! Escape your resort and …More

Ocho Rios, Jamaica

5.0 (32)

ATV, Bamboo Rafting, and Horseback Ride Tour From Montego Bay

3 thrilling activities, 2 unforgettable cities! Discover the ultimate Jamaican adventure with our ATV, Bamboo Rafting, and Horseback Riding combo tour! Escape your resort and...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (32)

from
$110

Dunn's River Catamaran Cruise From Ocho Rios

Set sail on a 4 hour catamaran cruise to Dunn's River Falls and along the way enjoy drinks, music, dancing and, of course our secret-ingredient …More

Ocho Rios, Jamaica

4.8 (111)

Dunn's River Catamaran Cruise From Ocho Rios

Set sail on a 4 hour catamaran cruise to Dunn's River Falls and along the way enjoy drinks, music, dancing and, of course our secret-ingredient...

4 hours Hotel pickup offered Free Cancellation

4.8 (111)

from
$142

Why plan your trip with us? At Otta Control Charters we make it our mission to ensure our guest relax and take a break from …More

Grand Cayman, Cayman Islands

5.0 (20)

Private Boat Tour in Cayman Islands

Why plan your trip with us? At Otta Control Charters we make it our mission to ensure our guest relax and take a break from...

3 hours Free Cancellation

5.0 (20)

from
$850

Escape to De Palm Island, Aruba's private coral island, where relaxation and adventure come together in one unforgettable day. Your admission includes unlimited food and …More

4.3 (348)

Aruba De Palm Island Day Pass

Escape to De Palm Island, Aruba's private coral island, where relaxation and adventure come together in one unforgettable day. Your admission includes unlimited food and...

6 hours Free Cancellation

4.3 (348)

from
$135

Isla Saona from Punta Cana: Catamaran and Boat Tour

Live the Magic of Saône Island! Ready to discover paradise? Just a few minutes by boat from La Romana beach ☀️ Beaches of Dream White …More

Punta Cana, Dominican Republic

4.8 (18)

Isla Saona from Punta Cana: Catamaran and Boat Tour

Live the Magic of Saône Island! Ready to discover paradise? Just a few minutes by boat from La Romana beach ☀️ Beaches of Dream White...

8 hours Hotel pickup offered Free Cancellation

4.8 (18)

from
$79

Private St. Lucia Snorkeling & Pitons Boat Adventure

Make every moment in Saint Lucia count! Skip the crowded buses and packed group tours and discover the island aboard your own private boat with …More

Marigot Bay, St Lucia

4.9 (26)

Private St. Lucia Snorkeling & Pitons Boat Adventure

Make every moment in Saint Lucia count! Skip the crowded buses and packed group tours and discover the island aboard your own private boat with...

4 hours Hotel pickup offered Free Cancellation

4.9 (26)

from
$99

Toro Negro River Hike & Cliff Jumping Adventure; San Juan Pick Up

This is hands down the best hike on the entire island. From breathtaking views, to cool natural tropical pools, to cliff jumps that can satisfy …More

5.0 (22)

Toro Negro River Hike & Cliff Jumping Adventure; San Juan Pick Up

This is hands down the best hike on the entire island. From breathtaking views, to cool natural tropical pools, to cliff jumps that can satisfy...

8 hours Free Cancellation

5.0 (22)

from
$165

Punta Cana Boat Cruise and Snorkeling with Open Bar

Enjoy our 3 hour Shared Boat Tour for adults and families with children and snorkel in the best coral reefs of Punta Cana. After the …More

Punta Cana, Dominican Republic

4.9 (25)

Punta Cana Boat Cruise and Snorkeling with Open Bar

Enjoy our 3 hour Shared Boat Tour for adults and families with children and snorkel in the best coral reefs of Punta Cana. After the...

4 hours Hotel pickup offered Free Cancellation

4.9 (25)

from
$55

Sail Away in Montego Bay on a Private Catamaran

Sailing along the coastline of Montego Bay offers breathtaking views and turquoise waters. You’ll have the opportunity to indulge in snorkeling and swimming, explore the …More

Montego Bay, Jamaica

5.0 (20)

Sail Away in Montego Bay on a Private Catamaran

Sailing along the coastline of Montego Bay offers breathtaking views and turquoise waters. You’ll have the opportunity to indulge in snorkeling and swimming, explore the...

3 hours Free Cancellation

5.0 (20)

from
$1,850

Small Group: Snorkeling Cruise Adventure around the Punta Cana Coast

SINGLES, COUPLES & GROUPS can all explore the beautiful coast of Punta Cana on this safe route. Embark on a party in one of the …More

Punta Cana, Dominican Republic

4.9 (38)

Small Group: Snorkeling Cruise Adventure around the Punta Cana Coast

SINGLES, COUPLES & GROUPS can all explore the beautiful coast of Punta Cana on this safe route. Embark on a party in one of the...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (38)

from
$60

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?