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 →

Green Grotto Caves Excursion from Montego Bay

The Green Grotto Caves, known at various times as the Runaway Bay Caves, are among Jamaica's most prominent natural attractions. Having seen visitors since the …More

Montego Bay, Jamaica

4.0 (1)

Green Grotto Caves Excursion from Montego Bay

The Green Grotto Caves, known at various times as the Runaway Bay Caves, are among Jamaica's most prominent natural attractions. Having seen visitors since the...

4 to 5 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$92

The Ghosts of San Juan: Private 2.5-hour Spooky Evening Tour

Your tour begins in Columbus Square, where your expert private guide will introduce you to the city’s tenuous relationship with the notorious explorer. In June …More

4.0 (1)

The Ghosts of San Juan: Private 2.5-hour Spooky Evening Tour

Your tour begins in Columbus Square, where your expert private guide will introduce you to the city’s tenuous relationship with the notorious explorer. In June...

2 hours 30 minutes Free Cancellation

4.0 (1)

from
$65

Santo Domingo Discovery City Tour from Punta Cana

Join us in a tour across the first city of Las Americas, visiting some of the main places of the city, such as the Museum …More

Punta Cana, Dominican Republic

4.0 (1)

Santo Domingo Discovery City Tour from Punta Cana

Join us in a tour across the first city of Las Americas, visiting some of the main places of the city, such as the Museum...

12 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$110

Local Bar Hop Tour in Montego Bay with private transportation

This private bar tour provides a fun-filled-100%-authentic-Jamaican-un-sugar-coated experience. The tour promotes Montego Bay’s amazing Local Bars. We will visit 6 - 7 bars and off …More

Montego Bay, Jamaica

4.0 (1)

Local Bar Hop Tour in Montego Bay with private transportation

This private bar tour provides a fun-filled-100%-authentic-Jamaican-un-sugar-coated experience. The tour promotes Montego Bay’s amazing Local Bars. We will visit 6 - 7 bars and off...

2 to 3 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$35

Negril Beach Experience & Rick's Cafe from Montego Bay

RICK’S CAFE was the first public bar and restaurant of its type on the West End Cliffs of Negril, offering an alternative to Negril's majestic seven …More

Montego Bay, Jamaica

4.0 (1)

Negril Beach Experience & Rick's Cafe from Montego Bay

RICK’S CAFE was the first public bar and restaurant of its type on the West End Cliffs of Negril, offering an alternative to Negril's majestic seven...

8 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$151

Private Rio Bueno River Adventure from Runaway Bay Hotels

Experience a day where you indulge yourself in the most electrifying moments doing up to two water sports activities in the Rio Bueno River. Choose …More

Runaway Bay, Jamaica

4.0 (1)

Private Rio Bueno River Adventure from Runaway Bay Hotels

Experience a day where you indulge yourself in the most electrifying moments doing up to two water sports activities in the Rio Bueno River. Choose...

7 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$174

Macao Beach Buggy Safari & Cenote Swimming

You’ll drive through winding rural dirt tracks through plantations all the way to the famous Domitai Cave Park and a replica Taino village. Then you'll …More

Punta Cana, Dominican Republic

4.0 (1)

Macao Beach Buggy Safari & Cenote Swimming

You’ll drive through winding rural dirt tracks through plantations all the way to the famous Domitai Cave Park and a replica Taino village. Then you'll...

4 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$99

Private Custom St Maarten Nightlife Tour

Are you looking for an unforgettable night in St. Maarten? Uncomplicated fun, a relaxing or exciting evening? We will arrange the best possible night for …More

Grand Case, St Maarten

4.0 (1)

Private Custom St Maarten Nightlife Tour

Are you looking for an unforgettable night in St. Maarten? Uncomplicated fun, a relaxing or exciting evening? We will arrange the best possible night for...

5 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$360

Night Tour of Rose Hall Haunted Mansion plus Luminous Lagoon

A fascinating experience awaits you as you as you enter the world of the White Witch plus a tour of the magical Luminous Lagoon as …More

Lucea, Jamaica

4.0 (1)

Night Tour of Rose Hall Haunted Mansion plus Luminous Lagoon

A fascinating experience awaits you as you as you enter the world of the White Witch plus a tour of the magical Luminous Lagoon as...

6 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$185

Jamaica Bobsled & Dunn's River Falls Adventure Tour from Runaway Bay

Plan a visit to the scenic tropical Parish of St. Ann, Jamaica where your adventure will take you on one wild ride! Inspired by the …More

Runaway Bay, Jamaica

4.0 (1)

Jamaica Bobsled & Dunn's River Falls Adventure Tour from Runaway Bay

Plan a visit to the scenic tropical Parish of St. Ann, Jamaica where your adventure will take you on one wild ride! Inspired by the...

6 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$219

Jamaica Bob Sled, Blue Hole & Bob Marley Nine Miles, 3 Tours from Ocho Rios

Add a hassle free, 3 days adventure tour package to your vacation in the beautiful town of Ocho Rios. Experience Bob Sled at Mystic Mountain, Blue …More

Ocho Rios, Jamaica

4.0 (1)

Jamaica Bob Sled, Blue Hole & Bob Marley Nine Miles, 3 Tours from Ocho Rios

Add a hassle free, 3 days adventure tour package to your vacation in the beautiful town of Ocho Rios. Experience Bob Sled at Mystic Mountain, Blue...

3 days Hotel pickup offered Free Cancellation

4.0 (1)

from
$303

Luxury Catamaran Cruise: Snorkel, Beach Club, Cenote & Open Bar

Set sail from the largest marina in the Caribbean on double-decker catamaran to explore the azure waters off Cap Cana. Begin your day with snorkeling …More

4.0 (1)

Luxury Catamaran Cruise: Snorkel, Beach Club, Cenote & Open Bar

Set sail from the largest marina in the Caribbean on double-decker catamaran to explore the azure waters off Cap Cana. Begin your day with snorkeling...

8 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$199

Shore Excursion: Small Group St Thomas Highlights Tour

This small group tour is the best way to see the Island still leaving time for you to see St Thomas yourself whilst in port. …More

4.0 (1)

Shore Excursion: Small Group St Thomas Highlights Tour

This small group tour is the best way to see the Island still leaving time for you to see St Thomas yourself whilst in port....

2 hours Free Cancellation

4.0 (1)

from
$157

Venture for a half or full day of new experiences - a true Dominican cultural exchange. Resorts are relaxing and wonderful without a doubt, but …More

Punta Cana, Dominican Republic

4.0 (1)

Cultural Safari Tour from Punta Cana

Venture for a half or full day of new experiences - a true Dominican cultural exchange. Resorts are relaxing and wonderful without a doubt, but...

8 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$85

Night tour to Coco Bongo Punta Cana from Santo Domingo with Open Bar

Our tour offers the ultimate night experience from Santo Domingo to the vibrant Coco Bongo Punta Cana. What sets us apart is our private round-trip …More

Santo Domingo, Dominican Republic

4.0 (1)

Night tour to Coco Bongo Punta Cana from Santo Domingo with Open Bar

Our tour offers the ultimate night experience from Santo Domingo to the vibrant Coco Bongo Punta Cana. What sets us apart is our private round-trip...

6 to 8 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$175

Horseback Ride & Catamaran Cruise -From MoBay, Negril, Ocho Rios

Our Horseback Ride & Catamaran Cruise Experience combines the charm of horseback riding with the relaxing beauty of the Caribbean Sea, giving you two unique …More

Lucea, Jamaica

4.0 (1)

Horseback Ride & Catamaran Cruise -From MoBay, Negril, Ocho Rios

Our Horseback Ride & Catamaran Cruise Experience combines the charm of horseback riding with the relaxing beauty of the Caribbean Sea, giving you two unique...

5 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$500

Portland Nature and Eco Tour -From Montego Bay, Negril, Ocho Rios

Stop At: Boston Bay, is a stunning coastal town with white sand beaches and turquoise waters. Known for water sports such as swimming, surfing, and …More

Lucea, Jamaica

4.0 (1)

Portland Nature and Eco Tour -From Montego Bay, Negril, Ocho Rios

Stop At: Boston Bay, is a stunning coastal town with white sand beaches and turquoise waters. Known for water sports such as swimming, surfing, and...

10 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$500

You will be filled with enticement of sampling a variety of Jamaica rum blend. Appleton Estate is pact with the experience of knowing how Appleton …More

Montego Bay, Jamaica

4.0 (1)

Appleton Estate Rum Private Tour

You will be filled with enticement of sampling a variety of Jamaica rum blend. Appleton Estate is pact with the experience of knowing how Appleton...

5 to 8 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$72

Private YS Falls & Appleton Estate Rum tour from Montego Bay

At YS Falls you can enjoy several activities. Take a refreshing swim in the natural pools, explore the lush surroundings, and experience the stunning waterfall. …More

Montego Bay, Jamaica

4.0 (1)

Private YS Falls & Appleton Estate Rum tour from Montego Bay

At YS Falls you can enjoy several activities. Take a refreshing swim in the natural pools, explore the lush surroundings, and experience the stunning waterfall....

7 hours 45 minutes Hotel pickup offered Free Cancellation

4.0 (1)

from
$259

Full day excursion to Saona Island from Uvero Alto wih snorkeling

Embark on a full-day adventure to explore the most impressive and hidden corners of Saona Island. Start by admiring Saona Marita Bay in Bayahibe, then …More

Punta Cana, Dominican Republic

4.0 (1)

Full day excursion to Saona Island from Uvero Alto wih snorkeling

Embark on a full-day adventure to explore the most impressive and hidden corners of Saona Island. Start by admiring Saona Marita Bay in Bayahibe, then...

8 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$170

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?