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 →

Our Tours are one of a kind. our goal is to give you the best experience tour you have ever gotten in your entire life. …More

Philipsburg, St Maarten

4.7 (42)

St.Martin/St.Maarten Magical Tour

Our Tours are one of a kind. our goal is to give you the best experience tour you have ever gotten in your entire life....

2 to 5 hours Hotel pickup offered Free Cancellation

4.7 (42)

from
$80

You will visit the famous Blue Hole, where you will get a chance to swim, swing, dive, climb or just watch. (All Entry Fees Included). …More

Kingston, Jamaica

4.9 (18)

Blue Hole from Ocho Rios

You will visit the famous Blue Hole, where you will get a chance to swim, swing, dive, climb or just watch. (All Entry Fees Included)....

2 hours Hotel pickup offered Free Cancellation

4.9 (18)

from
$32

Half Day Grenada Sunshine Highlights Tour

Experience beautiful Grenada as you drive through St.George’s along the Western side of the Island through the fishing villages, viewing the Caribbean Sea. Drive through …More

4.8 (182)

Half Day Grenada Sunshine Highlights Tour

Experience beautiful Grenada as you drive through St.George’s along the Western side of the Island through the fishing villages, viewing the Caribbean Sea. Drive through...

4 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (182)

from
$75

FUN DAY St.Maarten Island Sightseeing Tour with Beach

Explore some of St Maarten's most famous spots on this island tour! Visit Oyster Bay for a picture stop, stop at Orient Bay for some …More

Grand Case, St Maarten

4.6 (231)

FUN DAY St.Maarten Island Sightseeing Tour with Beach

Explore some of St Maarten's most famous spots on this island tour! Visit Oyster Bay for a picture stop, stop at Orient Bay for some...

5 to 6 hours Hotel pickup offered Free Cancellation

4.6 (231)

from
$70

Enjoy a breath taking 2 1/2 hours All Terrain Vehicle (ATV) excursion through the islands most exquisite old sugar cane trails which consist of the …More

4.9 (70)

Jungle Bikes ATV Tour in St Kitts

Enjoy a breath taking 2 1/2 hours All Terrain Vehicle (ATV) excursion through the islands most exquisite old sugar cane trails which consist of the...

2 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (70)

from
$125

Half Day Excursion Colonial Zone Lighthouse to Colón and Tres Ojos from Santo Domingo

In this experience we will visit each iconic place in the tourist center of Santo Domingo and we will be providing information in great detail …More

Santo Domingo, Dominican Republic

4.5 (48)

Half Day Excursion Colonial Zone Lighthouse to Colón and Tres Ojos from Santo Domingo

In this experience we will visit each iconic place in the tourist center of Santo Domingo and we will be providing information in great detail...

4 hours Hotel pickup offered Free Cancellation

4.5 (48)

from
$90

The Ultimate Dominican Horseback Riding Adventure

We specialize in semi-private tours (no more than 10 riders at the time) where you are free to roam about our over 1,000 acre cattle …More

Punta Cana, Dominican Republic

4.9 (126)

The Ultimate Dominican Horseback Riding Adventure

We specialize in semi-private tours (no more than 10 riders at the time) where you are free to roam about our over 1,000 acre cattle...

5 hours Hotel pickup offered Free Cancellation

4.9 (126)

from
$99

Saona Island Tour: Small Group Trip on Trimaran Motorise

Come and enjoy a day on the island of Saona in a small group, far from the tourist hordes. On a comfortable motorized trimaran suitable …More

5.0 (47)

Saona Island Tour: Small Group Trip on Trimaran Motorise

Come and enjoy a day on the island of Saona in a small group, far from the tourist hordes. On a comfortable motorized trimaran suitable...

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (47)

from
$110

St. Nicholas Abbey Rum & Heritage Experience

Spend a memorable afternoon stepping back in time at St. Nicholas Abbey, one of the Caribbean’s most treasured attractions. This beautifully preserved plantation house is …More

Speightstown, Barbados

4.5 (52)

St. Nicholas Abbey Rum & Heritage Experience

Spend a memorable afternoon stepping back in time at St. Nicholas Abbey, one of the Caribbean’s most treasured attractions. This beautifully preserved plantation house is...

4 hours Hotel pickup offered Free Cancellation

4.5 (52)

from
$104

The tour starts in the capital of Saint Lucia historical site Marigot Bay, Banana Plantation, rum tasting site moving on to Soufriere visiting the Caribbean …More

Castries, St Lucia

5.0 (25)

St Lucia Island Excursion Day Tour

The tour starts in the capital of Saint Lucia historical site Marigot Bay, Banana Plantation, rum tasting site moving on to Soufriere visiting the Caribbean...

6 hours Hotel pickup offered Free Cancellation

5.0 (25)

from
$80

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

This excursion is the perfect combination because you have it all: beach, culture, nature, history, time to buy gifts, relaxation and fun. …More

Puerto Plata, Dominican Republic

4.9 (24)

City Tour with Beach and Lunch Included

This excursion is the perfect combination because you have it all: beach, culture, nature, history, time to buy gifts, relaxation and fun....

4 hours Hotel pickup offered Free Cancellation

4.9 (24)

from
$67

Visit one of Jamaica's top natural attractions — The Blue Hole in Ocho Rios. With private round trip transportation provided, all you have to do …More

Falmouth, Jamaica

5.0 (21)

Private Blue Hole Tour from Montego Bay

Visit one of Jamaica's top natural attractions — The Blue Hole in Ocho Rios. With private round trip transportation provided, all you have to do...

2 hours Hotel pickup offered Free Cancellation

5.0 (21)

from
$60

Explore Negril Day Tour beach and Ricks Cafe From Montego Bay

Enjoy our hassle-free day tour starting with a stop for shopping along the famous Hip Strip or at other local souvenir shops. We’ll then visit …More

Lucea, Jamaica

5.0 (20)

Explore Negril Day Tour beach and Ricks Cafe From Montego Bay

Enjoy our hassle-free day tour starting with a stop for shopping along the famous Hip Strip or at other local souvenir shops. We’ll then visit...

6 to 8 hours Hotel pickup offered Free Cancellation

5.0 (20)

from
$129

Private Guided Group Full-Day Water Tour fr Kingston to Portland

Discover the natural beauty and charm of Jamaica with this affordable private water adventure from Kingston to Portland, return, via St. Thomas. Free pickup from …More

Kingston, Jamaica

5.0 (25)

Private Guided Group Full-Day Water Tour fr Kingston to Portland

Discover the natural beauty and charm of Jamaica with this affordable private water adventure from Kingston to Portland, return, via St. Thomas. Free pickup from...

8 to 10 hours Hotel pickup offered Free Cancellation

5.0 (25)

from
$350

Our day tour goes through the mountainous terrain of Jamaica's South coast. The *Appleton Estate* home of one of the oldest commercially produced *Rums* in …More

Lucea, Jamaica

4.9 (20)

Appleton Estate Rum and Ys Falls Tour

Our day tour goes through the mountainous terrain of Jamaica's South coast. The *Appleton Estate* home of one of the oldest commercially produced *Rums* in...

7 to 8 hours Hotel pickup offered Free Cancellation

4.9 (20)

from
$130

Take a ride on the wild side on our amazing ATV safari tour through the brilliant Jamaican backcountry and enjoy the outback, a small Jamaican …More

Montego Bay, Jamaica

4.9 (140)

Chukka ATV Safari

Take a ride on the wild side on our amazing ATV safari tour through the brilliant Jamaican backcountry and enjoy the outback, a small Jamaican...

120 to 210 minutes Hotel pickup offered Free Cancellation

4.9 (140)

from
$139

Submerge yourself deep into the routs and what Santo Domingo culture has to offer! We will experience a tour full of historic events, historic sights, …More

4.8 (37)

Full-Day Guided Tour in santo Domingo

Submerge yourself deep into the routs and what Santo Domingo culture has to offer! We will experience a tour full of historic events, historic sights,...

5 hours Free Cancellation

4.8 (37)

from
$55

Private Sunset Catamaran Adventure Cruise with Open Bar

This sunset cruise is the perfect combination of a relaxing and exiting experience. You will be able to adjust the cruise to your personal preference …More

5.0 (22)

Private Sunset Catamaran Adventure Cruise with Open Bar

This sunset cruise is the perfect combination of a relaxing and exiting experience. You will be able to adjust the cruise to your personal preference...

2 hours

5.0 (22)

from
$1,800

Private Charter 37' Axopar in US Virgin Islands

Stormy Pirates Boat Charters is a family owned and operated company serving both St.Thomas and St. John. This private trip is completely customizable for your …More

5.0 (85)

Private Charter 37' Axopar in US Virgin Islands

Stormy Pirates Boat Charters is a family owned and operated company serving both St.Thomas and St. John. This private trip is completely customizable for your...

6 hours

5.0 (85)

from
$1,695

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?