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 →

Negrils Seven Miles Beach, Rick's cafe and Parasailing Tour.

This exclusive combo offers travelers the best of Jamaica’s must-do experiences! Start by unwinding on the pristine shores of the iconic Seven Mile Beach, where …More

Montego Bay, Jamaica

4.9 (18)

Negrils Seven Miles Beach, Rick's cafe and Parasailing Tour.

This exclusive combo offers travelers the best of Jamaica’s must-do experiences! Start by unwinding on the pristine shores of the iconic Seven Mile Beach, where...

8 hours Hotel pickup offered Free Cancellation

4.9 (18)

from
$180

Buggy and ATV Tour in Punta Cana Taina Cave and Macau Beach

- 3- to 4-hour tour by buggy or ATV in Punta Cana - Stops in Cueva Taina, Playa Macau and typical Dominican house - Professional …More

Punta Cana, Dominican Republic

4.9 (18)

Buggy and ATV Tour in Punta Cana Taina Cave and Macau Beach

- 3- to 4-hour tour by buggy or ATV in Punta Cana - Stops in Cueva Taina, Playa Macau and typical Dominican house - Professional...

3 to 4 hours Hotel pickup offered Free Cancellation

4.9 (18)

from
$36

4hr Private Luxury Yacht with Snorkeling, DJ, Bar, Food

This 47 foot catamaran is the luxurious way to experience Montego Bay by sea. Guests can enjoy an indoor, air-conditioned cabin with a full premium …More

5.0 (18)

4hr Private Luxury Yacht with Snorkeling, DJ, Bar, Food

This 47 foot catamaran is the luxurious way to experience Montego Bay by sea. Guests can enjoy an indoor, air-conditioned cabin with a full premium...

4 hours Free Cancellation

5.0 (18)

from
$4,300

Blue hole waterfalls + horseback riding combo tour from Ocho Rios

This tour satisfies the people who are looking to have a great/wonderful experience on their vacation, which we think is everyone. Best way to do …More

Ocho Rios, Jamaica

4.9 (18)

Blue hole waterfalls + horseback riding combo tour from Ocho Rios

This tour satisfies the people who are looking to have a great/wonderful experience on their vacation, which we think is everyone. Best way to do...

3 to 4 hours Hotel pickup offered Free Cancellation

4.9 (18)

from
$115

The Estate is located in Nassau Valley in the parish of St. Elizabeth, on Jamaica’s South Coast. If you like rum, you will have a …More

Negril, Jamaica

4.8 (18)

Appleton Estate Rum Tour

The Estate is located in Nassau Valley in the parish of St. Elizabeth, on Jamaica’s South Coast. If you like rum, you will have a...

6 hours Hotel pickup offered Free Cancellation

4.8 (18)

from
$70

Old San Juan Walking Tour with a Historian

As featured in National Geographic Traveller (UK) Discover Old San Juan through the lens of history on a guided walking tour led by a professional …More

4.8 (18)

Old San Juan Walking Tour with a Historian

As featured in National Geographic Traveller (UK) Discover Old San Juan through the lens of history on a guided walking tour led by a professional...

3 hours Free Cancellation

4.8 (18)

from
$85

[PRIVATE]Dunn's River & Martha Brae Rafting - Entrance & Lunch

If you love water and nature, then this is the tour for you. At Dunns River, you will experience a breathtaking waterfall that empties into …More

Lucea, Jamaica

4.9 (18)

[PRIVATE]Dunn's River & Martha Brae Rafting - Entrance & Lunch

If you love water and nature, then this is the tour for you. At Dunns River, you will experience a breathtaking waterfall that empties into...

5 to 6 hours Hotel pickup offered Free Cancellation

4.9 (18)

from
$285

Negril, Seven Mile Beach, Rick's Cafe Private Day Tour

Experience paradise and see Jamaica like never before with Deano’s Jamaica Tours. Whether you’re looking to see the sights or get off the beaten track, …More

Montego Bay, Jamaica

5.0 (18)

Negril, Seven Mile Beach, Rick's Cafe Private Day Tour

Experience paradise and see Jamaica like never before with Deano’s Jamaica Tours. Whether you’re looking to see the sights or get off the beaten track,...

6 to 12 hours Hotel pickup offered Free Cancellation

5.0 (18)

from
$125

Private Tour: Barbados Catamaran Snorkeling Cruise

While you’re in paradise, treat yourself to a private catamaran cruise along Barbados’ west coast. Spread out and relax with your family and friends on …More

5.0 (18)

Private Tour: Barbados Catamaran Snorkeling Cruise

While you’re in paradise, treat yourself to a private catamaran cruise along Barbados’ west coast. Spread out and relax with your family and friends on...

5 hours

5.0 (18)

from
$3,210

North and South Tour + Beach Time with a Local Native Guide

It is a Unique Small Group Tour guided by a knowledgeable, Local Bonaire resident who Loves the Island! Why Shekhinah Tours is Different: Unlike other …More

Kralendijk, Bonaire

4.8 (17)

North and South Tour + Beach Time with a Local Native Guide

It is a Unique Small Group Tour guided by a knowledgeable, Local Bonaire resident who Loves the Island! Why Shekhinah Tours is Different: Unlike other...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (17)

from
$105

Avocat Waterfall and Maracas Bay Experience

Discover the stunning **Avocat Waterfall**, located near the charming village of **Blanchisseuse** on Trinidad’s scenic northern coast. Begin with a short hike through lush rainforest …More

4.9 (17)

Avocat Waterfall and Maracas Bay Experience

Discover the stunning **Avocat Waterfall**, located near the charming village of **Blanchisseuse** on Trinidad’s scenic northern coast. Begin with a short hike through lush rainforest...

7 hours Hotel pickup offered Free Cancellation

4.9 (17)

from
$105

Experience for families and friends by private boat with pick-up

Spend the best experience for you and your family at sea in Punta Cana aboard the Miss Joma catamaran, animated by a staff that will …More

Punta Cana, Dominican Republic

5.0 (17)

Experience for families and friends by private boat with pick-up

Spend the best experience for you and your family at sea in Punta Cana aboard the Miss Joma catamaran, animated by a staff that will...

3 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$695

The Gros Piton Hike is a challenging yet rewarding hike done on the island. It is not for the faint of heart or for persons …More

Soufriere, St Lucia

4.8 (17)

Gros Piton Hike St Lucia

The Gros Piton Hike is a challenging yet rewarding hike done on the island. It is not for the faint of heart or for persons...

6 to 7 hours Hotel pickup offered Free Cancellation

4.8 (17)

from
$111

3H or 4H | Private Boat Trip with Snorkeling and Swimming

With this private tour you decide the pace. We can take groups up to 8 people. The crew recommends a combination of snorkeling, sightseeing and …More

5.0 (17)

3H or 4H | Private Boat Trip with Snorkeling and Swimming

With this private tour you decide the pace. We can take groups up to 8 people. The crew recommends a combination of snorkeling, sightseeing and...

3 hours Free Cancellation

5.0 (17)

from
$600

Bamboo Rafting & Limestone Foot Massage on the River

Embark on a captivating bamboo river rafting adventure at Lethe, Jamaica, where nature, culture, and relaxation blend effortlessly. This unforgettable experience takes you down the …More

Montego Bay, Jamaica

4.9 (17)

Bamboo Rafting & Limestone Foot Massage on the River

Embark on a captivating bamboo river rafting adventure at Lethe, Jamaica, where nature, culture, and relaxation blend effortlessly. This unforgettable experience takes you down the...

3 hours Hotel pickup offered Free Cancellation

4.9 (17)

from
$67

Gilmore tours offers top quality services, safe, reliable, friendly, and dependable, guaranteed to give you a memorable experience while you enjoy this beautiful island in …More

Kingston, Jamaica

5.0 (17)

Bamboo Rafting in Ocho Rios

Gilmore tours offers top quality services, safe, reliable, friendly, and dependable, guaranteed to give you a memorable experience while you enjoy this beautiful island in...

2 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$60

Hop aboard our colorful open-air beach bus and set off on a scenic ride through Aruba’s most iconic landmarks. Begin your morning at Aruba Aloe, …More

Palm - Eagle Beach, Aruba

5.0 (17)

Open Air Beach Bus Tour of Aruba

Hop aboard our colorful open-air beach bus and set off on a scenic ride through Aruba’s most iconic landmarks. Begin your morning at Aruba Aloe,...

5 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$50

YS Falls, Black River Safari, and Floyd's Pelican Bar Day-Trip (Transportation)

This unique tour takes you through the interior of the rain forest. The first stop is Y.S. Falls where you can enjoy nature in its …More

Montego Bay, Jamaica

4.9 (17)

YS Falls, Black River Safari, and Floyd's Pelican Bar Day-Trip (Transportation)

This unique tour takes you through the interior of the rain forest. The first stop is Y.S. Falls where you can enjoy nature in its...

8 to 9 hours Hotel pickup offered Free Cancellation

4.9 (17)

from
$67

Blue Hole Private Custom Day Trip from Montego Bay

This excursion is already customized to suit you’re needs but, you can add a few other stop or you’re choice in between the pick up …More

Runaway Bay, Jamaica

5.0 (17)

Blue Hole Private Custom Day Trip from Montego Bay

This excursion is already customized to suit you’re needs but, you can add a few other stop or you’re choice in between the pick up...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$100

Private Tour from Falmouth to Ocho Rios Blue Hole and Tubing

WELCOME TO TOUR JAMAICA TODAY. Your tour begins as you leave your hotel or cruise ship as your driver greet you with a smile and …More

Trelawny, Jamaica

4.8 (17)

Private Tour from Falmouth to Ocho Rios Blue Hole and Tubing

WELCOME TO TOUR JAMAICA TODAY. Your tour begins as you leave your hotel or cruise ship as your driver greet you with a smile and...

5 to 10 hours Hotel pickup offered Free Cancellation

4.8 (17)

from
$80

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?