Top Caribbean Luxury & Special Occasions

Q: Which Caribbean Luxury & Special Occasions have Instant Confirmation?

Caribbean Luxury & Special Occasions with Instant Confirmation include: San Juan Guided Turtle Snorkel Tour and Complimentary Videos Top Rated El Yunque Rainforest & Waterslide – SmallGroup Tour Island Jeep Safari with Natural Pool Baby Beach and Lunch Aruba UTV & ATV Adventure Half-Day Yunque Rainforest Waterslide & rope swing Guided Tour View all Tours with Instant Confirmation →

Q: I need a ride! Which Caribbean Luxury & Special Occasions have Hotel Pickup?

No problem. These Caribbean Luxury & Special Occasions include Hotel Pickup: Island Jeep Safari with Natural Pool Baby Beach and Lunch Aruba UTV & ATV Adventure Aruba UTV Adventure: Animal Garden, North Coast & Andicuri Beach Monkeyland and Plantation Safari Tour from Punta Cana Full-Day Santo Domingo City Tour from Punta Cana 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 →

Seeking a romantic evening for two, a serene escape from the bustling city, or simply a moment of tranquillity amidst nature's splendor, our Private Sunset …More

Marigot Bay, St Lucia

5.0 (16)

Private Sunset and Snorkel Cruise

Seeking a romantic evening for two, a serene escape from the bustling city, or simply a moment of tranquillity amidst nature's splendor, our Private Sunset...

2 hours Hotel pickup offered Free Cancellation

5.0 (16)

from
$150

This is an adventure that You get to experience a natural waterfall in the rainforest, and what you want to do. You will be picked …More

Runaway Bay, Jamaica

5.0 (16)

Blue Hole and Shopping in Ochi Rios

This is an adventure that You get to experience a natural waterfall in the rainforest, and what you want to do. You will be picked...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (16)

from
$43

Travel at a relaxed pace along the scenic north coast of Trinidad, making several stops for bathing and admiring the views, on this 8-hour guided …More

4.9 (16)

Coastal Tour of Trinidad

Travel at a relaxed pace along the scenic north coast of Trinidad, making several stops for bathing and admiring the views, on this 8-hour guided...

8 hours Hotel pickup offered Free Cancellation

4.9 (16)

from
$105

Puerto Plata City Tour with beach Taino bay & amber cove

Get some relaxing day exploring during this half day , guided , historical city tour in puerto plata Learn about the city and then head …More

4.8 (16)

Puerto Plata City Tour with beach Taino bay & amber cove

Get some relaxing day exploring during this half day , guided , historical city tour in puerto plata Learn about the city and then head...

4 hours 10 minutes Free Cancellation

4.8 (16)

from
$60

Golden beach - transportation Amber Cove and Taino bay

Discover one of the Dominican Republic most sought after beach golden beach. after pick up from Either amber cove or taino bay port enjoy our …More

4.8 (16)

Golden beach - transportation Amber Cove and Taino bay

Discover one of the Dominican Republic most sought after beach golden beach. after pick up from Either amber cove or taino bay port enjoy our...

4 hours Free Cancellation

4.8 (16)

from
$45

Luxury Catamaran Sunset Sail with Saxophone on Princess Grace

What could be a better end to a day full of Caribbean sun and surf than a relaxing sunset sail aboard a luxury sailing catamaran? …More

4.9 (16)

Luxury Catamaran Sunset Sail with Saxophone on Princess Grace

What could be a better end to a day full of Caribbean sun and surf than a relaxing sunset sail aboard a luxury sailing catamaran?...

1 hour 30 minutes Free Cancellation

4.9 (16)

from
$139

Dunn's River Falls & Horseback Riding Adventure from ocho rios

Get ready for an unforgettable Jamaican adventure! Ride horseback through tropical trails and along a beautiful beach, then climb the world-famous Dunn’s River Falls, feeling …More

Runaway Bay, Jamaica

5.0 (16)

Dunn's River Falls & Horseback Riding Adventure from ocho rios

Get ready for an unforgettable Jamaican adventure! Ride horseback through tropical trails and along a beautiful beach, then climb the world-famous Dunn’s River Falls, feeling...

8 hours Hotel pickup offered Free Cancellation

5.0 (16)

from
$140

Buggies Adventure in Punta Cana 4 Hours Off-Road Fun

Unique adventure! Buggies, indigenous cave and Macau Beach, all with transportation included. Know how Indians lived. …More

Punta Cana, Dominican Republic

4.9 (16)

Buggies Adventure in Punta Cana 4 Hours Off-Road Fun

Unique adventure! Buggies, indigenous cave and Macau Beach, all with transportation included. Know how Indians lived....

4 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (16)

from
$35

Blue Room and Beach Tour Curacao by Speedboat

The tour with pick-up takes about 5 hours. Includes: lunch, snacks, drinks and snorkel set. First we will sail to the Blue Room, then we …More

Willemstad, Curacao

4.9 (16)

Blue Room and Beach Tour Curacao by Speedboat

The tour with pick-up takes about 5 hours. Includes: lunch, snacks, drinks and snorkel set. First we will sail to the Blue Room, then we...

5 hours Free Cancellation

4.9 (16)

from
$110

Private Full Day Sail in Virgin Islands National Park

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some …More

5.0 (16)

Private Full Day Sail in Virgin Islands National Park

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some...

6 hours Free Cancellation

5.0 (16)

from
$1,650

Don't Worry - Full Day Private Catamaran Cruise - St Maarten

Join us on Don't Worry, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can …More

5.0 (16)

Don't Worry - Full Day Private Catamaran Cruise - St Maarten

Join us on Don't Worry, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can...

8 hours Free Cancellation

5.0 (16)

from
$235

The trip Includes : a snorkel to see the marine life of Punta Cana in the "Sanctuary Reef" and anchor in a sandbar of 3-4 …More

Punta Cana, Dominican Republic

5.0 (16)

Cap Cana Private Family Catamaran

The trip Includes : a snorkel to see the marine life of Punta Cana in the "Sanctuary Reef" and anchor in a sandbar of 3-4...

3 hours Hotel pickup offered Free Cancellation

5.0 (16)

from
$950

Immerse yourself in the unforgettable allure of Anguilla on your private boat, a day that will linger in your memory. Let Pierre be your expert …More

4.8 (16)

Full Day Anguilla Private Charter Tour

Immerse yourself in the unforgettable allure of Anguilla on your private boat, a day that will linger in your memory. Let Pierre be your expert...

8 hours Free Cancellation

4.8 (16)

from
$1,637

Reggae Family Catamaran Cruise From Montego Bay

Take in the wonders of the island from the best seat in the house on board the Island Routes Reggae Family Catamaran Cruise. Get ready …More

Montego Bay, Jamaica

4.8 (16)

Reggae Family Catamaran Cruise From Montego Bay

Take in the wonders of the island from the best seat in the house on board the Island Routes Reggae Family Catamaran Cruise. Get ready...

3 hours Hotel pickup offered Free Cancellation

4.8 (16)

from
$125

Bamboo Rafting & Horseback Ride n Swim Guided Tour In Montego Bay

Bamboo rafting and Horseback ride are two of the top things to do while on vacation in Jamaica. Escape the confines of your hotel resort …More

Montego Bay, Jamaica

4.8 (16)

Bamboo Rafting & Horseback Ride n Swim Guided Tour In Montego Bay

Bamboo rafting and Horseback ride are two of the top things to do while on vacation in Jamaica. Escape the confines of your hotel resort...

3 to 4 hours Hotel pickup offered Free Cancellation

4.8 (16)

from
$145

Visit the Morne Trois Pitons National Park, UNESCO World Heritage Site Visit the twin Trafalgar Waterfalls Visit the Wotten Waven Sulphur springs Visit Champagne beach …More

4.9 (16)

Waterfall And Champagne Reef Adventure

Visit the Morne Trois Pitons National Park, UNESCO World Heritage Site Visit the twin Trafalgar Waterfalls Visit the Wotten Waven Sulphur springs Visit Champagne beach...

4 hours Hotel pickup offered Free Cancellation

4.9 (16)

from
$120

Private Tour to Dunn's River Falls From Ocho Rios

This tour is a top tourist attraction in Ocho Rios, Jamaica. You will climb the 600-foot falls and enjoy the cool refreshing water. Swim in …More

Ocho Rios, Jamaica

5.0 (16)

Private Tour to Dunn's River Falls From Ocho Rios

This tour is a top tourist attraction in Ocho Rios, Jamaica. You will climb the 600-foot falls and enjoy the cool refreshing water. Swim in...

2 hours Hotel pickup offered Free Cancellation

5.0 (16)

from
$60

Private Charter from St Martin to St Barth

Your group will be taken to St Barth on an open, fast and comfortable Donzi 35' . You will leave from Anse Marcel (or other pick up upon request), and …More

5.0 (16)

Private Charter from St Martin to St Barth

Your group will be taken to St Barth on an open, fast and comfortable Donzi 35' . You will leave from Anse Marcel (or other pick up upon request), and...

8 hours Free Cancellation

5.0 (16)

from
$2,100

Explore Puerto Plata on this half-day tour. Listen to informative and entertaining commentary from your Tour guide, 4 hours visiting local landmarks such as the …More

Puerto Plata, Dominican Republic

5.0 (16)

Puerto Plata City tour

Explore Puerto Plata on this half-day tour. Listen to informative and entertaining commentary from your Tour guide, 4 hours visiting local landmarks such as the...

4 hours 15 minutes Hotel pickup offered Free Cancellation

5.0 (16)

from
$65

Private Tour 45ft Powerboat to Nearby Islands

Enjoy an islanding hopping tour to nearby islands. You can choose to do snorkeling beautiful coral reefs, Gilligan's island, green cay and you can even …More

5.0 (16)

Private Tour 45ft Powerboat to Nearby Islands

Enjoy an islanding hopping tour to nearby islands. You can choose to do snorkeling beautiful coral reefs, Gilligan's island, green cay and you can even...

4 hours

5.0 (16)

from
$3,800

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Caribbean Luxury & Special Occasions?

What are the best kid-friendly options for Caribbean Luxury & Special Occasions Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean Luxury & Special Occasions are:

View all kid-friendly Tours →

Which Caribbean Luxury & Special Occasions have Instant Confirmation?

Which Caribbean Luxury & Special Occasions have Free Cancellation?

Caribbean Luxury & Special Occasions 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 Luxury & Special Occasions have Hotel Pickup?

Got any more Caribbean trip ideas?

What are the most popular styles of Tours and Activities in Caribbean?