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 Full-Day Aruba History and Must-See Landmarks Tour Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Nassau Swimming Pigs: Snorkeling, Lunch & Private Beach Club 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 Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Full-Day Aruba History and Must-See Landmarks Tour San Juan Sunset Harbor Boat Ride 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 →

St. Kitts: Open-Air Trolley Food City Tour with Tastings

Sugar City Express is operating the only open-air island trolley food tour in St. Kitts. 3 hours. 4 authentic tastings. Pure Caribbean flavor. Open-Air Island …More

4.8 (4)

St. Kitts: Open-Air Trolley Food City Tour with Tastings

Sugar City Express is operating the only open-air island trolley food tour in St. Kitts. 3 hours. 4 authentic tastings. Pure Caribbean flavor. Open-Air Island...

2 to 3 hours Free Cancellation

4.8 (4)

from
$105

This unique combo tour allows travelers to experience four accelerating, exciting and once in a life time experience. 1.The Sky Explorer takes you over 100 …More

Montego Bay, Jamaica

5.0 (2)

Full Day Ocho Rios Combo Tour

This unique combo tour allows travelers to experience four accelerating, exciting and once in a life time experience. 1.The Sky Explorer takes you over 100...

7 to 9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$230

With a name like Paradise Island, you'd only expect the best. So, a VIP experience is just what you'll get with this full day island …More

Puerto Plata, Dominican Republic

4.0 (5)

Cayo Arena Exclusive Tour with Lunch

With a name like Paradise Island, you'd only expect the best. So, a VIP experience is just what you'll get with this full day island...

9 hours Hotel pickup offered Free Cancellation

4.0 (5)

from
$150

3 Hour Jet ski Adventure Swim with Rays and More

Explore the Cayman Islands on a fun and exciting jet ski tour you'll be able to enjoy swimming with the Stingrays, snorkel with marine life, …More

Grand Cayman, Cayman Islands

4.6 (9)

3 Hour Jet ski Adventure Swim with Rays and More

Explore the Cayman Islands on a fun and exciting jet ski tour you'll be able to enjoy swimming with the Stingrays, snorkel with marine life,...

3 hours Free Cancellation

4.6 (9)

from
$375

Port Of Spain Private Walking Tour With A Guide (Private tour)

Get to know the city through the eyes of a local guide. With no set itinerary, you can customize the tour or leave it to …More

5.0 (2)

Port Of Spain Private Walking Tour With A Guide (Private tour)

Get to know the city through the eyes of a local guide. With no set itinerary, you can customize the tour or leave it to...

3 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$67

Luminous Lagoon Boat Tour from Montego Bay

This lagoon, surrounded by mangroves, is home to microscopic organisms that emit a phosphorescent light when agitated. The water glows a beautiful blue and becomes …More

Montego Bay, Jamaica

5.0 (1)

Luminous Lagoon Boat Tour from Montego Bay

This lagoon, surrounded by mangroves, is home to microscopic organisms that emit a phosphorescent light when agitated. The water glows a beautiful blue and becomes...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$151

Bamboo Rafting, Limestone Foot Massage, Parasailing Private Tour

Take a journey in the rural parts of Montego Bay{Country) and rap yourself with with nature.Lethe Bamboo Rafting is the best way to have REAL …More

Montego Bay, Jamaica

5.0 (3)

Bamboo Rafting, Limestone Foot Massage, Parasailing Private Tour

Take a journey in the rural parts of Montego Bay{Country) and rap yourself with with nature.Lethe Bamboo Rafting is the best way to have REAL...

3 to 6 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$250

Negril 7 Miles Beach, Ricks Cafe and Shopping

This tour allows guest to do shopping and interact with locals and experience beautiful western Jamaica sunset while being entertainment. Guest will have their entire …More

Montego Bay, Jamaica

5.0 (4)

Negril 7 Miles Beach, Ricks Cafe and Shopping

This tour allows guest to do shopping and interact with locals and experience beautiful western Jamaica sunset while being entertainment. Guest will have their entire...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$48

Discover the Dunn's River Waterfalls and have a great time during this experience that takes you to the interior of Jamaica to enjoy one of …More

Montego Bay, Jamaica

5.0 (2)

Dunn's River Falls Private Tour

Discover the Dunn's River Waterfalls and have a great time during this experience that takes you to the interior of Jamaica to enjoy one of...

3 to 5 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$85

Private Ocho Rios highlights and beach day tour

Visitors get to experience Ocho Rios at a very low cost, air conditioned vehicle and with a guide that this is their home town. A …More

Ocho Rios, Jamaica

5.0 (2)

Private Ocho Rios highlights and beach day tour

Visitors get to experience Ocho Rios at a very low cost, air conditioned vehicle and with a guide that this is their home town. A...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$51

Blue Hole & River Tubing (GROUP) Transportation Only

We provide first class service and the best on the island. Safety is our main priority so for every time we pick you up from …More

Ocho Rios, Jamaica

5.0 (2)

Blue Hole & River Tubing (GROUP) Transportation Only

We provide first class service and the best on the island. Safety is our main priority so for every time we pick you up from...

3 hours 45 minutes Hotel pickup offered Free Cancellation

5.0 (2)

from
$250

Larimar mine, ALL INCLUSIVE experience, from Barahona

The experience includes lunch and we take care that you do not have to worry about transportation, giving you the convenience of being picked up …More

5.0 (3)

Larimar mine, ALL INCLUSIVE experience, from Barahona

The experience includes lunch and we take care that you do not have to worry about transportation, giving you the convenience of being picked up...

6 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$93

Bob Marley's Birth Place( NINE MILE )Tour

Enjoy this day trip to Nine Miles, St. Ann to visit the birth and resting place of the late reggae legend, Bob Marley. At 3,000 …More

Montego Bay, Jamaica

5.0 (2)

Bob Marley's Birth Place( NINE MILE )Tour

Enjoy this day trip to Nine Miles, St. Ann to visit the birth and resting place of the late reggae legend, Bob Marley. At 3,000...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$100

Luminous Lagoon Small Group Tour from Ocho Rios

Located in Falmouth, Trelawny the Luminous Lagoon (Glistening Waters) is a natural wonder. Here, guests are taken to a phosphorescent lagoon where they will embark …More

Ocho Rios, Jamaica

4.6 (7)

Luminous Lagoon Small Group Tour from Ocho Rios

Located in Falmouth, Trelawny the Luminous Lagoon (Glistening Waters) is a natural wonder. Here, guests are taken to a phosphorescent lagoon where they will embark...

3 hours Hotel pickup offered Free Cancellation

4.6 (7)

from
$140

The buggy excursion is a very complete excursion of the area, where you will visit one of the very famous beaches of the Dominican Republic …More

Punta Cana, Dominican Republic

5.0 (1)

4 Hour Speed Experience in Punta Cana

The buggy excursion is a very complete excursion of the area, where you will visit one of the very famous beaches of the Dominican Republic...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$64

Private Yacht with snorkelling from Montego Bay

Welcome to luxury on your very own private yacht while you explore the hidden islands off the coast of the Montego Bay shoreline. A warm …More

Montego Bay, Jamaica

5.0 (2)

Private Yacht with snorkelling from Montego Bay

Welcome to luxury on your very own private yacht while you explore the hidden islands off the coast of the Montego Bay shoreline. A warm...

4 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (2)

from
$4,000

St. Kitts Rainforest Rumble (with Snacks)

Distinguishing features Biodiversity: The forest is rich and has a diverse ecosystem showcasing a wide variety of flora and fauna. Its dense vegetation of some …More

5.0 (1)

St. Kitts Rainforest Rumble (with Snacks)

Distinguishing features Biodiversity: The forest is rich and has a diverse ecosystem showcasing a wide variety of flora and fauna. Its dense vegetation of some...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$75

Day Trip to The Bob Marley Museum from Montego Bay

Travel to Kingston, the capital of Jamaica, on a day trip from Montego Bay. Take the opportunity during the 3-hour drive up Jamaica's North Coast …More

Montego Bay, Jamaica

4.4 (7)

Day Trip to The Bob Marley Museum from Montego Bay

Travel to Kingston, the capital of Jamaica, on a day trip from Montego Bay. Take the opportunity during the 3-hour drive up Jamaica's North Coast...

10 to 12 hours Hotel pickup offered Free Cancellation

4.4 (7)

from
$2,500

Montego Bay Highlights with Local Guide & Private Transportation

Prepare for an extraordinary adventure with our customizable "Montego Bay Highlights Tour." This immersive experience will take you deep into the heart and soul of …More

Montego Bay, Jamaica

5.0 (2)

Montego Bay Highlights with Local Guide & Private Transportation

Prepare for an extraordinary adventure with our customizable "Montego Bay Highlights Tour." This immersive experience will take you deep into the heart and soul of...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$45

Nine Miles located in the rural hills of St Ann is the birthplace and final resting place of Bob Marley. Bob Marley grew up in …More

Trelawny, Jamaica

5.0 (2)

Bob Marley Nine Mile Private Tour

Nine Miles located in the rural hills of St Ann is the birthplace and final resting place of Bob Marley. Bob Marley grew up in...

5 to 7 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$95

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?