Top Caribbean Luxury & Special Occasions

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

Caribbean Luxury & Special Occasions with Instant Confirmation include: Discover El Yunque National Park: Half-Day Rainforest Tour Half-Day Aruba Island Tour from Oranjestad Nassau Swimming Pigs: Snorkeling, Lunch & Private Beach Club San Juan Sunset Harbor Boat Ride Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise 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: Discover El Yunque National Park: Half-Day Rainforest Tour Half-Day Aruba Island Tour from Oranjestad 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 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 →

Private Luxury Dinner Sunset Cruise in St. Lucia

Join us for a Private Dinner Sunset Cruise with a Chef onboard to provide a culinary experience that is second to none. We will cruise …More

Choc, St Lucia

Private Luxury Dinner Sunset Cruise in St. Lucia

Join us for a Private Dinner Sunset Cruise with a Chef onboard to provide a culinary experience that is second to none. We will cruise...

3 hours Hotel pickup offered Free Cancellation

from
$1,600

Blue Mountains, Port Royal and Kingston 2-Day Tour from Ocho Rios

Leave Ocho Rios behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation …More

Ocho Rios, Jamaica

Blue Mountains, Port Royal and Kingston 2-Day Tour from Ocho Rios

Leave Ocho Rios behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation...

2 days Hotel pickup offered Free Cancellation

from
$1,077

5 Day Package to Santiago and Puerto Plata with Accommodation

Immerse yourself in the Dominican essence with our exclusive 4 nights and 5 days package! Start your adventure in the heart of Santiago de los …More

Puerto Plata, Dominican Republic

5 Day Package to Santiago and Puerto Plata with Accommodation

Immerse yourself in the Dominican essence with our exclusive 4 nights and 5 days package! Start your adventure in the heart of Santiago de los...

5 days Free Cancellation

from
$3,440

Private Catamaran and Sunset Cruise to Ricks Cafe from Negril

Basically this completely private cruise is family friendly and perfect for small groups and special celebrations such as birthdays, anniversaries ect. We cater for any …More

Negril, Jamaica

Private Catamaran and Sunset Cruise to Ricks Cafe from Negril

Basically this completely private cruise is family friendly and perfect for small groups and special celebrations such as birthdays, anniversaries ect. We cater for any...

4 to 5 hours Hotel pickup offered

from
$4,100

Experience our Private Tour to Black Sand Beach in The Southeast of Puerto Rico! Embark on a serene journey through the picturesque landscapes of Puerto …More

Private Tour to Black Sand Beach in The Southeast of Puerto Rico

Experience our Private Tour to Black Sand Beach in The Southeast of Puerto Rico! Embark on a serene journey through the picturesque landscapes of Puerto...

7 hours Hotel pickup offered Free Cancellation

from
$292

7-Day Bus Tour Across Jamaica from Montego Bay

Experience Jamaica, its people, places, culture, heritage and delicious local cuisines! Travel along coastal roads with the blue Caribbean Sea as your backdrop. Pass through …More

Montego Bay, Jamaica

7-Day Bus Tour Across Jamaica from Montego Bay

Experience Jamaica, its people, places, culture, heritage and delicious local cuisines! Travel along coastal roads with the blue Caribbean Sea as your backdrop. Pass through...

7 days Free Cancellation

from
$2,769

Utuado Canyon River and Waterfall Private Tour in Puerto Rico

Experience our Utuado Canyon, River & Waterfall Private Tour in Puerto Rico! Embark on a serene journey through the picturesque landscapes of Puerto Rico as …More

Utuado, Puerto Rico

Utuado Canyon River and Waterfall Private Tour in Puerto Rico

Experience our Utuado Canyon, River & Waterfall Private Tour in Puerto Rico! Embark on a serene journey through the picturesque landscapes of Puerto Rico as...

8 hours Hotel pickup offered Free Cancellation

from
$292

Blue Mountains, Port Royal and Kingston 2-Day Tour from Runaway Bay

Leave Runaway Bay behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation …More

Runaway Bay, Jamaica

Blue Mountains, Port Royal and Kingston 2-Day Tour from Runaway Bay

Leave Runaway Bay behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation...

2 days Hotel pickup offered Free Cancellation

from
$1,128

Discover the pristine beauty of Culebra on a luxurious 6-hour boat tour aboard a 36 ft yacht. Experience a secure and comfortable navigation and discover …More

Culebra All Inclusive Luxury Private Yacht Tour

Discover the pristine beauty of Culebra on a luxurious 6-hour boat tour aboard a 36 ft yacht. Experience a secure and comfortable navigation and discover...

6 hours Free Cancellation

from
$2,700

Experience nature and the beauty of Jamaica with the Family Eco Adventure Tour, a true learning experience for both you and the family. Best of …More

Ocho Rios, Jamaica

Island Explorer 7 Days North Coast Tour

Experience nature and the beauty of Jamaica with the Family Eco Adventure Tour, a true learning experience for both you and the family. Best of...

7 days Hotel pickup offered Free Cancellation

from
$2,750

Exuma, located just 40 miles from Nassau , is a stunning tropical paradise known for its crystal-clear turquoise waters, pristine white sandy beaches, and an …More

Private Exuma Cays Day: Iguana, Shark, Pigs, Sandbar & Lunch

Exuma, located just 40 miles from Nassau , is a stunning tropical paradise known for its crystal-clear turquoise waters, pristine white sandy beaches, and an...

8 hours Free Cancellation

from
$8,500

When was the last time you went out for a casual drive and ended up inside a volcano? A surreal scenario comes to life at …More

Discover St.Lucia Multi day Tour

When was the last time you went out for a casual drive and ended up inside a volcano? A surreal scenario comes to life at...

5 days Hotel pickup offered Free Cancellation

from
$1,200

Experience our Private Scuba Diving Tour in San Juan! Embark on a serene journey through the picturesque landscapes of Puerto Rico as you make your …More

Private Scuba Diving Tour in San Juan

Experience our Private Scuba Diving Tour in San Juan! Embark on a serene journey through the picturesque landscapes of Puerto Rico as you make your...

3 hours 30 minutes Hotel pickup offered Free Cancellation

from
$394

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

Private Yacht Tour w/optional Flying Dress Photoshoot Montego Bay

Luxurious Ultimate Private Caribbean Vacation Package!! 3-hour cruise includes: Various refreshments, including (Premium Alcohol and Rum Punch). Choice of KFC Chicken (includes fries, biscuits) or …More

Montego Bay, Jamaica

Private Yacht Tour w/optional Flying Dress Photoshoot Montego Bay

Luxurious Ultimate Private Caribbean Vacation Package!! 3-hour cruise includes: Various refreshments, including (Premium Alcohol and Rum Punch). Choice of KFC Chicken (includes fries, biscuits) or...

3 hours Hotel pickup offered Free Cancellation

from
$2,844

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

Basically this completely private fishing trip is perfect for the whole family, with private roundtrip transportation and a certified crew you can expect to get …More

Montego Bay, Jamaica

Private Deep Sea Fishing in Montego Bay

Basically this completely private fishing trip is perfect for the whole family, with private roundtrip transportation and a certified crew you can expect to get...

4 hours Hotel pickup offered Free Cancellation

from
$1,800

Robinson Crusoe Island Beach Hideaway Cruise Come aboard in Turks and Caicos for your amazing adventure on the crystal clear waters of TCI. We welcome …More

Robinson Crusoe Island Beach Hideaway Cruise

Robinson Crusoe Island Beach Hideaway Cruise Come aboard in Turks and Caicos for your amazing adventure on the crystal clear waters of TCI. We welcome...

4 hours Hotel pickup offered Free Cancellation

from
$2,963

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! We …More

Private Half Day Afternoon Snorkel and Cruise on Serendipity

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! We...

4 hours Hotel pickup offered Free Cancellation

from
$2,897

Indulge in the ultimate luxury with a private charter to St. Barts. Experience unparalleled comfort aboard high-end vessel, customized to your desires. Whether you're cruising …More

Saint Barth Prestige Private Charter

Indulge in the ultimate luxury with a private charter to St. Barts. Experience unparalleled comfort aboard high-end vessel, customized to your desires. Whether you're cruising...

6 to 8 hours Free Cancellation

from
$1,600

Frequently Asked Questions

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

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?