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 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 Full-Day Aruba History and Must-See Landmarks Tour Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Aruba UTV & ATV 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 →

Private Grenada Tour: Tailor-Made for Your Perfect Day

Fully customizable private tour — design your own pace and choose your preferred stops. Experience Grenada’s highlights: tropical waterfalls, artisan chocolate, historic rum distillery, and …More

5.0 (6)

Private Grenada Tour: Tailor-Made for Your Perfect Day

Fully customizable private tour — design your own pace and choose your preferred stops. Experience Grenada’s highlights: tropical waterfalls, artisan chocolate, historic rum distillery, and...

7 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$205

Ocho Rios and Blue Hole Eco Experience from Kingston

Embark on a captivating ecotour experience at Blue Hole in Ocho Rios, Jamaica, where nature's wonders unfold in a pristine and sustainable setting. This eco-friendly …More

Kingston, Jamaica

5.0 (1)

Ocho Rios and Blue Hole Eco Experience from Kingston

Embark on a captivating ecotour experience at Blue Hole in Ocho Rios, Jamaica, where nature's wonders unfold in a pristine and sustainable setting. This eco-friendly...

4 hours Free Cancellation

5.0 (1)

from
$270

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

Negril Highlights Catamaran Cruise With Stop At Margaritaville

Test your skills with this 4 hour one-of-a-kind challenge, that begins with a wet ‘n’ wild adventure full of mouthwatering appetizers and exotic cocktails aboard …More

Negril, Jamaica

4.8 (9)

Negril Highlights Catamaran Cruise With Stop At Margaritaville

Test your skills with this 4 hour one-of-a-kind challenge, that begins with a wet ‘n’ wild adventure full of mouthwatering appetizers and exotic cocktails aboard...

4 hours Hotel pickup offered Free Cancellation

4.8 (9)

from
$140

Negril 45-minute Guided Horseback Ride and Swim

Saddle up for a one-of-a-kind adventure at Jamwest Motorsports & Adventure Park! After pickup from Negril or Montego Bay, enjoy a scenic safari ride to …More

Lucea, Jamaica

3.7 (59)

Negril 45-minute Guided Horseback Ride and Swim

Saddle up for a one-of-a-kind adventure at Jamwest Motorsports & Adventure Park! After pickup from Negril or Montego Bay, enjoy a scenic safari ride to...

2 to 4 hours Hotel pickup offered Free Cancellation

3.7 (59)

from
$95

Dunn's River Falls, ATV, Horseback Ride and Bamboo Rafting Tour

Embark on an epic journey with 876 Adventures LLC and experience four exhilarating activities in a single day! First, conquer the iconic Dunn's River Falls …More

Montego Bay, Jamaica

5.0 (7)

Dunn's River Falls, ATV, Horseback Ride and Bamboo Rafting Tour

Embark on an epic journey with 876 Adventures LLC and experience four exhilarating activities in a single day! First, conquer the iconic Dunn's River Falls...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$140

Jet Car Experience in Montego Bay with Private Transfer

Experience the thrill of a lifetime with our jet car adventure in Montego Bay! Feel the adrenaline rush as you race along the picturesque coastline …More

Montego Bay, Jamaica

4.8 (5)

Jet Car Experience in Montego Bay with Private Transfer

Experience the thrill of a lifetime with our jet car adventure in Montego Bay! Feel the adrenaline rush as you race along the picturesque coastline...

2 hours Hotel pickup offered Free Cancellation

4.8 (5)

from
$30

Blue Hole, Secret falls & Bamboo River Rafting from Montego Bay

Visit Ocho Rios one of the most CHILLED location in Jamaica and soak up some island vibes! This is a relaxed yet fun filled experience …More

Montego Bay, Jamaica

5.0 (8)

Blue Hole, Secret falls & Bamboo River Rafting from Montego Bay

Visit Ocho Rios one of the most CHILLED location in Jamaica and soak up some island vibes! This is a relaxed yet fun filled experience...

6 to 7 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$75

Blue Hole and Dunns River Falls the Number One Rated Excursions

Discover the allure of Jamaica's natural wonders with "Blue Hole and Dunn's River Falls Tour" by Premier Transfers and Tours. Immerse yourself in the vibrant …More

Runaway Bay, Jamaica

5.0 (7)

Blue Hole and Dunns River Falls the Number One Rated Excursions

Discover the allure of Jamaica's natural wonders with "Blue Hole and Dunn's River Falls Tour" by Premier Transfers and Tours. Immerse yourself in the vibrant...

6 to 7 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$140

Self-Driven MINI Cooper Tour From Montego Bay To Negril

Buckle up and take the wheel of your own MINI Cooper during this 6 and a half hour journey along Jamaica’s beautiful north-west coast to the …More

Montego Bay, Jamaica

4.7 (17)

Self-Driven MINI Cooper Tour From Montego Bay To Negril

Buckle up and take the wheel of your own MINI Cooper during this 6 and a half hour journey along Jamaica’s beautiful north-west coast to the...

6 hours 30 minutes Hotel pickup offered Free Cancellation

4.7 (17)

from
$164

Experience the best of Antigua and Barbuda nightlife as we visit various clubs! Enjoy a night of unforgettable partying in a luxurious setting with top-notch …More

Five Islands Village, Antigua and Barbuda

4.9 (7)

Nightlife Tour of Antigua and Barbuda

Experience the best of Antigua and Barbuda nightlife as we visit various clubs! Enjoy a night of unforgettable partying in a luxurious setting with top-notch...

4 hours Hotel pickup offered Free Cancellation

4.9 (7)

from
$80

Coffee & Waterfalls Tour: from the mountains to the cup

Discover the magic of Puerto Rico’s central mountains on our Coffee & Waterfalls Tour in Ciales — a full-sensory adventure that combines rich coffee culture …More

Isla Verde, Puerto Rico

5.0 (6)

Coffee & Waterfalls Tour: from the mountains to the cup

Discover the magic of Puerto Rico’s central mountains on our Coffee & Waterfalls Tour in Ciales — a full-sensory adventure that combines rich coffee culture...

7 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$285

Private Half Day Tour in St. Thomas Virgin Islands with Guide

Embark on an exhilarating island tour in St. Thomas, Virgin Islands, and prepare to be blown away by the sheer beauty and excitement that awaits …More

Cruz Bay, US Virgin Islands

5.0 (2)

Private Half Day Tour in St. Thomas Virgin Islands with Guide

Embark on an exhilarating island tour in St. Thomas, Virgin Islands, and prepare to be blown away by the sheer beauty and excitement that awaits...

4 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$600

Crystal Caves and Bermuda Underwater Exploration Institute Admission

This is a great way to learn about the unique diversity of Bermuda's Marine life and eco system, while enjoying the beautiful wildlife found on …More

4.5 (14)

Crystal Caves and Bermuda Underwater Exploration Institute Admission

This is a great way to learn about the unique diversity of Bermuda's Marine life and eco system, while enjoying the beautiful wildlife found on...

4 hours Hotel pickup offered

4.5 (14)

from
$159

Horseback Riding, ATV and Blue Hole Water Falls Tour in Jamaica

The tour offers a thrilling mix of diverse experiences that cater to both adventure seekers and nature lovers. Here's what makes it stand out: The …More

Lucea, Jamaica

5.0 (5)

Horseback Riding, ATV and Blue Hole Water Falls Tour in Jamaica

The tour offers a thrilling mix of diverse experiences that cater to both adventure seekers and nature lovers. Here's what makes it stand out: The...

6 to 8 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$110

Dominica Treasures: Waterfalls, Hot Springs, & Titou Gorge

Get ready for an exciting experience as you join our intimate group activity, with just 2-5 couples max! Soon, you’ll be able to swim, soak, …More

4.8 (6)

Dominica Treasures: Waterfalls, Hot Springs, & Titou Gorge

Get ready for an exciting experience as you join our intimate group activity, with just 2-5 couples max! Soon, you’ll be able to swim, soak,...

5 hours Free Cancellation

4.8 (6)

from
$110

Santo Domingo Full-Day Tour: Colonial Zone & Los Tres Ojos

Your adventure begins with a comfortable ride from Punta Cana, allowing you to soak in the scenic beauty of the Dominican countryside as you make …More

Santo Domingo, Dominican Republic

5.0 (6)

Santo Domingo Full-Day Tour: Colonial Zone & Los Tres Ojos

Your adventure begins with a comfortable ride from Punta Cana, allowing you to soak in the scenic beauty of the Dominican countryside as you make...

9 to 10 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$95

Join us on a scenic journey highlighting the rustic side of the South Coast of Jamaica in visiting the Pelican Bar. The bar is located …More

Montego Bay, Jamaica

4.6 (10)

Floyd's Pelican Bar Private Tour

Join us on a scenic journey highlighting the rustic side of the South Coast of Jamaica in visiting the Pelican Bar. The bar is located...

5 to 7 hours Hotel pickup offered Free Cancellation

4.6 (10)

from
$86

Punta Cana Caribbean Party Boat with snorkeling

Get the party started with this entertaining snorkeling cruise that showcases the best of beaches, boats and underwater worlds. Cruise the Bavaro coast while you …More

Punta Cana, Dominican Republic

5.0 (6)

Punta Cana Caribbean Party Boat with snorkeling

Get the party started with this entertaining snorkeling cruise that showcases the best of beaches, boats and underwater worlds. Cruise the Bavaro coast while you...

3 hours Free Cancellation

5.0 (6)

from
$69

First Class Lounge, Fast Track & Round Trip Private Airport Transport Package

Getting in and out of Montego Bay’s Sangster International Airport couldn’t be any easier. A round-trip private hotel transfer completes this package, which includes access to …More

Ocho Rios, Jamaica

4.7 (16)

First Class Lounge, Fast Track & Round Trip Private Airport Transport Package

Getting in and out of Montego Bay’s Sangster International Airport couldn’t be any easier. A round-trip private hotel transfer completes this package, which includes access to...

1 hour Hotel pickup offered

4.7 (16)

from
$115

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?

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

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?