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) 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 →

Bamboo River Rafting with Negril Ricks Cafe Visit

Bamboo Rafting, Margaritaville & Rick’s Café – A One-of-a-Kind Jamaican Experience Get ready for a day that blends relaxation, culture, and adventure — Real Tours …More

Lucea, Jamaica

4.5 (10)

Bamboo River Rafting with Negril Ricks Cafe Visit

Bamboo Rafting, Margaritaville & Rick’s Café – A One-of-a-Kind Jamaican Experience Get ready for a day that blends relaxation, culture, and adventure — Real Tours...

6 to 7 hours Hotel pickup offered Free Cancellation

4.5 (10)

from
$165

River Tubing and Blue Hole Tour from Ocho Rios

Have a blast on this combo private tour to the blue hole and calypso tubing for a fun-filled day of activities. Come and enjoy the …More

Ocho Rios, Jamaica

5.0 (8)

River Tubing and Blue Hole Tour from Ocho Rios

Have a blast on this combo private tour to the blue hole and calypso tubing for a fun-filled day of activities. Come and enjoy the...

4 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$100

Party Boat Booze Cruise - Crucero con bebidas y Fiesta en Barco

Enjoy views of the Dominican Republic's east coast aboard a catamaran cruise from Punta Cana. Relax on board the boat and sip drinks from the …More

5.0 (5)

Party Boat Booze Cruise - Crucero con bebidas y Fiesta en Barco

Enjoy views of the Dominican Republic's east coast aboard a catamaran cruise from Punta Cana. Relax on board the boat and sip drinks from the...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (5)

from
$65

Lethe Bamboo Rafting, ATV, Horseback Riding Tour in Montego Bay

Discover the ultimate Jamaican adventure with our ATV, Bamboo Rafting, and Horseback Riding combo tour! Escape your resort and dive into the beauty and excitement …More

Falmouth, Jamaica

5.0 (5)

Lethe Bamboo Rafting, ATV, Horseback Riding Tour in Montego Bay

Discover the ultimate Jamaican adventure with our ATV, Bamboo Rafting, and Horseback Riding combo tour! Escape your resort and dive into the beauty and excitement...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$399

FULL DAY BIG GAME FISHING Hours : 8.00 am - 04.00 pm Location: Puerto Plata - Sosua - Cabarete - Amber Cove All excursions …More

Puerto Plata, Dominican Republic

5.0 (2)

Full Day Big Game Fishing

FULL DAY BIG GAME FISHING Hours : 8.00 am - 04.00 pm Location: Puerto Plata - Sosua - Cabarete - Amber Cove All excursions...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$980

Spend the day in Les Saintes or Guadeloupe or Martinique or Marie Galante (French Islands) relaxing on the beach of just being in the French …More

5.0 (1)

Boat Cruise to the French Islands

Spend the day in Les Saintes or Guadeloupe or Martinique or Marie Galante (French Islands) relaxing on the beach of just being in the French...

8 to 10 hours Hotel pickup offered

5.0 (1)

from
$2,500

Adventurers learn the secrets of conch hunting and join the captain and crew at a secret spot on a bold underwater quest for conch. After …More

4.8 (9)

Seaside Scavenger Hunt Turks & Caicos

Adventurers learn the secrets of conch hunting and join the captain and crew at a secret spot on a bold underwater quest for conch. After...

3 hours Hotel pickup offered

4.8 (9)

from
$160

Punta Cana Combo Tour: Dune Buggy Safari and Snorkeling Cruise

Discover spectacular places. Walk past tobacco, palm and banana plantations to reach one of our natural treasures: the Taíno Ecological Park. Once there, you will …More

Punta Cana, Dominican Republic

5.0 (3)

Punta Cana Combo Tour: Dune Buggy Safari and Snorkeling Cruise

Discover spectacular places. Walk past tobacco, palm and banana plantations to reach one of our natural treasures: the Taíno Ecological Park. Once there, you will...

1 day 8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$148

St. John's,Antigua Horse Back Riding & bareback swim & Fort beach

Embark on an unforgettable excursion starting at Heritage Quay, proceeding to the stunning Fort James Beach. Guests will enjoy 1 hour & 30 minutes beach …More

Five Islands Village, Antigua and Barbuda

4.7 (17)

St. John's,Antigua Horse Back Riding & bareback swim & Fort beach

Embark on an unforgettable excursion starting at Heritage Quay, proceeding to the stunning Fort James Beach. Guests will enjoy 1 hour & 30 minutes beach...

2 hours 40 minutes Hotel pickup offered Free Cancellation

4.7 (17)

from
$136

Small-Group Family Fun Boat & Snorkeling Cruise (Drinks & Snacks)

"Enjoy the high-energy fun of a party boat without the overwhelming crowds. This small-group, family-friendly cruise offers the perfect mix of snorkeling, music, and paradise—safe …More

3.8 (25)

Small-Group Family Fun Boat & Snorkeling Cruise (Drinks & Snacks)

"Enjoy the high-energy fun of a party boat without the overwhelming crowds. This small-group, family-friendly cruise offers the perfect mix of snorkeling, music, and paradise—safe...

4 hours Hotel pickup offered Free Cancellation

3.8 (25)

from
$59

Martha Brae River Rafting & Luminous Lagoon Private Tour Falmouth

Make the most out of your travel when in Jamaica. Book your private transfer with us and we will take you on an amazing journey. …More

5.0 (6)

Martha Brae River Rafting & Luminous Lagoon Private Tour Falmouth

Make the most out of your travel when in Jamaica. Book your private transfer with us and we will take you on an amazing journey....

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$195

Rastafari Safari Cultural ATV Ride & Ricks Cafe Combo

Enjoy an authentic experience of rural Jamaica and the picturesque ocean coastline of Negril on this private tour. This experience starts with a scenic journey …More

Montego Bay, Jamaica

5.0 (2)

Rastafari Safari Cultural ATV Ride & Ricks Cafe Combo

Enjoy an authentic experience of rural Jamaica and the picturesque ocean coastline of Negril on this private tour. This experience starts with a scenic journey...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$145

4 Activities Combo Boat Tour with ATV Montego Bay

Basically this tour offers travelers 4 combined tours all in one day. with your own personal tour guide you can expect to go through all …More

Montego Bay, Jamaica

5.0 (5)

4 Activities Combo Boat Tour with ATV Montego Bay

Basically this tour offers travelers 4 combined tours all in one day. with your own personal tour guide you can expect to go through all...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$232

Hop on our comfortable 55ft President Yacht and enjoy a semi beach hopping yacht cruise in Curacao. Our yacht cruise will start exploring the spanish …More

4.0 (27)

Half day private yacht cruise & snorkel

Hop on our comfortable 55ft President Yacht and enjoy a semi beach hopping yacht cruise in Curacao. Our yacht cruise will start exploring the spanish...

4 hours Free Cancellation

4.0 (27)

from
$1,250

Tet Paul Hike & Soufriere Catamaran Experience

Experience the allure of Soufriere as you embark on a scenic cruise down the West Coast of St. Lucia. On arrival to Soufriere you will …More

Choc, St Lucia

4.3 (3)

Tet Paul Hike & Soufriere Catamaran Experience

Experience the allure of Soufriere as you embark on a scenic cruise down the West Coast of St. Lucia. On arrival to Soufriere you will...

8 hours Hotel pickup offered Free Cancellation

4.3 (3)

from
$165

One unique highlight of a sunset cocktail cruise is the breathtaking view of the sunset over the water as you enjoy delicious cocktails and appetizers. …More

5.0 (4)

Catamaran Sunset and Cocktail Cruise

One unique highlight of a sunset cocktail cruise is the breathtaking view of the sunset over the water as you enjoy delicious cocktails and appetizers....

3 hours Free Cancellation

5.0 (4)

from
$95

Full day tour Samana, Las Terrenas and El Limón from Santo Domingo

This full day tour full of unforgettable experiences, is a specialized tour for you who want to discover the unknown places of the bay of …More

Santo Domingo, Dominican Republic

4.0 (3)

Full day tour Samana, Las Terrenas and El Limón from Santo Domingo

This full day tour full of unforgettable experiences, is a specialized tour for you who want to discover the unknown places of the bay of...

8 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$200

Party on the Parasailing boat in Punta Cana

What really makes our tour special is the unique mix of water activities and adventures that we have organized to ensure that you have an …More

5.0 (7)

Party on the Parasailing boat in Punta Cana

What really makes our tour special is the unique mix of water activities and adventures that we have organized to ensure that you have an...

4 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$105

Rafting with Limestone Massage Lethe and free shuttle to Parties

We provide a safe, reliable, and friendly service for travelers of all ages. With Tropical Travels, you will experience the authentic side of Jamaica — …More

Lucea, Jamaica

5.0 (9)

Rafting with Limestone Massage Lethe and free shuttle to Parties

We provide a safe, reliable, and friendly service for travelers of all ages. With Tropical Travels, you will experience the authentic side of Jamaica —...

1 hour Hotel pickup offered Free Cancellation

5.0 (9)

from
$85

Private ATVRide From Montego Great River Rafting and Foot Massage

If you’re a person that love to enjoy adventurous events this tour is one fit for you, hop a board a 4 wheeler Atv bike …More

Montego Bay, Jamaica

5.0 (1)

Private ATVRide From Montego Great River Rafting and Foot Massage

If you’re a person that love to enjoy adventurous events this tour is one fit for you, hop a board a 4 wheeler Atv bike...

2 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$230

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?