Top Caribbean Luxury & Special Occasions

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 →

Private Boat Tour with Snorkeling Island Hopping and Noahs Ark

Our well-known and experienced Captain, with over 20 years of boating experience, knows all the hidden gems of the surrounding islands. His expertise, enthusiasm, dedication …More

5.0 (64)

Private Boat Tour with Snorkeling Island Hopping and Noahs Ark

Our well-known and experienced Captain, with over 20 years of boating experience, knows all the hidden gems of the surrounding islands. His expertise, enthusiasm, dedication...

4 hours Free Cancellation

5.0 (64)

from
$1,450

Private Snorkeling Charter to Pinel, Tintamarre islands and more

Feel the freedom of the Caribbean Sea with a completely private experience tailored to your pace and interests. St. Maarten/Saint Martin is one of the …More

5.0 (12)

Private Snorkeling Charter to Pinel, Tintamarre islands and more

Feel the freedom of the Caribbean Sea with a completely private experience tailored to your pace and interests. St. Maarten/Saint Martin is one of the...

6 hours Free Cancellation

5.0 (12)

from
$1,450

Half Day Snorkeling, Sightseeing & Island Hopping Private Charter

Our morning private boat tour is a great way to start the day. We venture away from the crowd and take you to some of …More

5.0 (147)

Half Day Snorkeling, Sightseeing & Island Hopping Private Charter

Our morning private boat tour is a great way to start the day. We venture away from the crowd and take you to some of...

4 hours Hotel pickup offered Free Cancellation

5.0 (147)

from
$1,488

Craft unforgettable memories on your private boat as you explore the breathtaking beauty of Saint-Martin. With Pierre as your guide, discover the hidden treasures of …More

5.0 (2)

Full Day St Martin Private Charter Tour

Craft unforgettable memories on your private boat as you explore the breathtaking beauty of Saint-Martin. With Pierre as your guide, discover the hidden treasures of...

8 hours Free Cancellation

5.0 (2)

from
$1,488

Saona island - Private Tour with a Luxury Speed Boat

Depart from Bayahibe aboard a unique, cigarette-style speed boat Boat equipped with sofa, one bedroom Maximum 6 people on board for your comfort Thanks to …More

Punta Cana, Dominican Republic

5.0 (10)

Saona island - Private Tour with a Luxury Speed Boat

Depart from Bayahibe aboard a unique, cigarette-style speed boat Boat equipped with sofa, one bedroom Maximum 6 people on board for your comfort Thanks to...

6 hours Hotel pickup offered Free Cancellation

5.0 (10)

from
$1,490

Discover the best of Turks & Caicos Islands aboard this catamaran combining luxury and comfort. Ideal to enjoy a day with friends, family or in …More

Private Sunset Tour Catamaran 44 Big Ben

Discover the best of Turks & Caicos Islands aboard this catamaran combining luxury and comfort. Ideal to enjoy a day with friends, family or in...

2 hours Free Cancellation

from
$1,490

Discover the best of Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or in …More

Private Sunset Tour Fjord 38 Ben

Discover the best of Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or in...

2 hours Free Cancellation

from
$1,490

Private Full Day Charter to Jost Van Dyke from US Virgin Islands

Sleep in, take it slow, and still have an incredible day exploring Jost Van Dyke. With a late departure at 11 AM and a return …More

5.0 (6)

Private Full Day Charter to Jost Van Dyke from US Virgin Islands

Sleep in, take it slow, and still have an incredible day exploring Jost Van Dyke. With a late departure at 11 AM and a return...

6 hours 30 minutes Free Cancellation

5.0 (6)

from
$1,495

Private Luxury Veuve Clicquot Sunset Champagne Yacht Charter

Your private group up to 12 individuals will enjoy a Luxury Sunset and Champagne cruise about our luxury 50' Voyage catamaran. We head out early …More

5.0 (2)

Private Luxury Veuve Clicquot Sunset Champagne Yacht Charter

Your private group up to 12 individuals will enjoy a Luxury Sunset and Champagne cruise about our luxury 50' Voyage catamaran. We head out early...

2 hours Free Cancellation

5.0 (2)

from
$1,495

Hell and Crystal Cave Adventure Private Tour

Our first stop will be at the Governor's Residence for optional pictures. Followed by another picture stop at the Old Home Stead. Then a change …More

Grand Cayman, Cayman Islands

5.0 (1)

Hell and Crystal Cave Adventure Private Tour

Our first stop will be at the Governor's Residence for optional pictures. Followed by another picture stop at the Old Home Stead. Then a change...

5 hours Free Cancellation

5.0 (1)

from
$1,495

Private 6 Days All Included Tour from Sto Domingo to Punta Cana

We are a subsidiary of Quetzal Excursions renowned for its quality, with over 10 years in tourism, our expertly crafted itinerary ensures excellence and inclusivity. …More

Santo Domingo, Dominican Republic

Private 6 Days All Included Tour from Sto Domingo to Punta Cana

We are a subsidiary of Quetzal Excursions renowned for its quality, with over 10 years in tourism, our expertly crafted itinerary ensures excellence and inclusivity....

6 days

from
$1,499

‘’An exclusive opportunity to discover the Dominican Republic with its history, landscapes, beaches and culture. A trip that combines from the colonial historical past to …More

Punta Cana, Dominican Republic

9 Days Multi-Day Tour in Punta Cana

‘’An exclusive opportunity to discover the Dominican Republic with its history, landscapes, beaches and culture. A trip that combines from the colonial historical past to...

9 days

from
$1,499

Enjoy all the beautiful beaches the Virgin Islands has to offer in the comfort and shade of a specifically charter designed boat with reclining bow …More

4.9 (96)

USVI Private Boat Charter Adventure

Enjoy all the beautiful beaches the Virgin Islands has to offer in the comfort and shade of a specifically charter designed boat with reclining bow...

8 hours Free Cancellation

4.9 (96)

from
$1,500

Join us for a personalized full island tour of Bermuda! Led by expert local guides, you’ll explore all nine parishes, visiting stunning hotspots while traveling …More

5.0 (7)

Bermudaful Island 6 Hours Private Tour

Join us for a personalized full island tour of Bermuda! Led by expert local guides, you’ll explore all nine parishes, visiting stunning hotspots while traveling...

6 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$1,500

Private Party Boat with Snorkeling in Punta Cana (Half Day)

Ready to enjoy a private booze cruise with your family and friends? Pleasant Tours offers the best service for your group, and you get the …More

Punta Cana, Dominican Republic

5.0 (2)

Private Party Boat with Snorkeling in Punta Cana (Half Day)

Ready to enjoy a private booze cruise with your family and friends? Pleasant Tours offers the best service for your group, and you get the...

3 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$1,500

Half Day Private Tour with Jet Ski Experience in Cayman Island

This is a private tour. Only your group will participate. Avoid the crowds of Stingray City aboard your own private, 11-passenger boat. Depart from the …More

Grand Cayman, Cayman Islands

5.0 (6)

Half Day Private Tour with Jet Ski Experience in Cayman Island

This is a private tour. Only your group will participate. Avoid the crowds of Stingray City aboard your own private, 11-passenger boat. Depart from the...

4 hours Free Cancellation

5.0 (6)

from
$1,500

Half-Day at Green Cay Bahamas Snorkeling with Turtles

Enjoy an excursion to Pearl Island for snorkeling with lovely fish. Green Cay where you can swim right up to the turtles in their natural …More

Nassau, Bahamas

5.0 (11)

Half-Day at Green Cay Bahamas Snorkeling with Turtles

Enjoy an excursion to Pearl Island for snorkeling with lovely fish. Green Cay where you can swim right up to the turtles in their natural...

4 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$1,500

Private Speedboat Charter: St Maarten to Anguilla

Discover Anguilla on a private speedboat charter from St Maarten! Visit the best snorkeling sites, stop at some of the most pristine islands or beach …More

5.0 (8)

Private Speedboat Charter: St Maarten to Anguilla

Discover Anguilla on a private speedboat charter from St Maarten! Visit the best snorkeling sites, stop at some of the most pristine islands or beach...

7 hours Free Cancellation

5.0 (8)

from
$1,500

Private Charter Around St Maarten-St.Martin

Private charter on our very comfortable Speed Boats .St.Maarten- St.martin, unique beaches, special atmosphere. we guarantee smooth ride and possibility go closest possible to your …More

5.0 (3)

Private Charter Around St Maarten-St.Martin

Private charter on our very comfortable Speed Boats .St.Maarten- St.martin, unique beaches, special atmosphere. we guarantee smooth ride and possibility go closest possible to your...

5 to 7 hours Free Cancellation

5.0 (3)

from
$1,500

Scuba Dive and Snorkel Private Charter in Puerto Rico

Because SCUBA diving and snorkeling in a natural aquarium is possible! If there is a certified diver in your party, we can easily arrange a …More

5.0 (3)

Scuba Dive and Snorkel Private Charter in Puerto Rico

Because SCUBA diving and snorkeling in a natural aquarium is possible! If there is a certified diver in your party, we can easily arrange a...

4 hours Free Cancellation

5.0 (3)

from
$1,500

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?

Caribbean Luxury & Special Occasions with Instant Confirmation include:

View all Tours with 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?

No problem. These Caribbean Luxury & Special Occasions include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Caribbean trip ideas?

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