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 →

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands. Looking for more time …More

5.0 (32)

Group Sunset Sail St. John

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands. Looking for more time...

2 hours 30 minutes Free Cancellation

5.0 (32)

from
$245

Historical Guided Walking Tour of Marigot by ISLAND FRIEND

Our historical visit to Marigot allows us to understand to travel through time and space as we stroll through the centuries, revealed by Marigot's streets …More

5.0 (6)

Historical Guided Walking Tour of Marigot by ISLAND FRIEND

Our historical visit to Marigot allows us to understand to travel through time and space as we stroll through the centuries, revealed by Marigot's streets...

1 hour 30 minutes Free Cancellation

5.0 (6)

from
$31

Shared Island Tour with Lunch & Admissions

Over the years of doing customized island tours, we have collected a selection of our valued customers "most wanted attractions" and created this SHARED tour …More

5.0 (23)

Shared Island Tour with Lunch & Admissions

Over the years of doing customized island tours, we have collected a selection of our valued customers "most wanted attractions" and created this SHARED tour...

6 hours Hotel pickup offered Free Cancellation

5.0 (23)

from
$209

Rum, Cigars and Espadrilles in Old San Juan

Embark on a unique adventure in Old San Juan, immersing yourself in the vibrant traditions of rum, cigars, and espadrilles. Discover hidden gems as you …More

5.0 (34)

Rum, Cigars and Espadrilles in Old San Juan

Embark on a unique adventure in Old San Juan, immersing yourself in the vibrant traditions of rum, cigars, and espadrilles. Discover hidden gems as you...

3 hours Free Cancellation

5.0 (34)

from
$180

Private Meet your Guide El Yunque and Waterslides Adventure

Connect with nature and breathe in the fresh air on this exhilarating tour to Las Tinajas in Ceiba, Puerto Rico. The clear trails make this …More

Fajardo, Puerto Rico

5.0 (10)

Private Meet your Guide El Yunque and Waterslides Adventure

Connect with nature and breathe in the fresh air on this exhilarating tour to Las Tinajas in Ceiba, Puerto Rico. The clear trails make this...

5 hours 30 minutes Free Cancellation

5.0 (10)

from
$600

El Yunque Rainforest- Water Slide, Luquillo Beach Guided Tour

Utopia Luxury Tours stands out from other tours by offering a unique experience that includes visits to four stunning locations, along with complimentary professional photos …More

4.6 (40)

El Yunque Rainforest- Water Slide, Luquillo Beach Guided Tour

Utopia Luxury Tours stands out from other tours by offering a unique experience that includes visits to four stunning locations, along with complimentary professional photos...

5 to 6 hours Free Cancellation

4.6 (40)

from
$89

Piton Sunset Snorkel Cruise St. Lucia From Castries

Enjoy a catamaran cruise to the majestic Pitons, swim and snorkel over protected reefs near the Pitons. Cruise up the coast to Marigot Bay, enjoy the …More

Choc, St Lucia

4.3 (57)

Piton Sunset Snorkel Cruise St. Lucia From Castries

Enjoy a catamaran cruise to the majestic Pitons, swim and snorkel over protected reefs near the Pitons. Cruise up the coast to Marigot Bay, enjoy the...

5 hours Hotel pickup offered

4.3 (57)

from
$111

Private St. George's Tour with Old State House Access

Explore the UNESCO World Heritage Town of St. George's on a private 2.5-hour historical walking tour. Enjoy exclusive interior access to the Old State House, …More

5.0 (5)

Private St. George's Tour with Old State House Access

Explore the UNESCO World Heritage Town of St. George's on a private 2.5-hour historical walking tour. Enjoy exclusive interior access to the Old State House,...

2 hours 30 minutes Free Cancellation

5.0 (5)

from
$95

Swimming with Horses at the Beach from Punta Cana Free transportation

Swim Horse Punta Cana was conceived in order to diversify the offering of sustainable and ecological tourism at the resort. Its symbol is the horse, …More

Punta Cana, Dominican Republic

4.5 (20)

Swimming with Horses at the Beach from Punta Cana Free transportation

Swim Horse Punta Cana was conceived in order to diversify the offering of sustainable and ecological tourism at the resort. Its symbol is the horse,...

4 hours Hotel pickup offered Free Cancellation

4.5 (20)

from
$119

Grab the wheel of your own 17 ft. speedboat as you cruise along the picturesque vistas of St. Lucia and into an enchanting snorkeling experience. …More

Rodney Bay, St Lucia

4.9 (27)

St. Lucia Drive and Snorkel Experience

Grab the wheel of your own 17 ft. speedboat as you cruise along the picturesque vistas of St. Lucia and into an enchanting snorkeling experience....

2 hours Hotel pickup offered

4.9 (27)

from
$226

Blue Hole and River Tubing Combo from Ocho Rios

After hotel or port pickup, enjoy a scenic drive to the Blue Hole. During the approximately 30 minute drive through the mountain, your guide will …More

Ocho Rios, Jamaica

4.8 (37)

Blue Hole and River Tubing Combo from Ocho Rios

After hotel or port pickup, enjoy a scenic drive to the Blue Hole. During the approximately 30 minute drive through the mountain, your guide will...

3 hours Free Cancellation

4.8 (37)

from
$40

Step aboard our 35’ Donzi center console for a private Cayman Islands adventure built entirely around you. A spacious layout, premium sound system, comfortable seating, …More

Grand Cayman, Cayman Islands

4.9 (26)

Private Boat Charter in Cayman Islands

Step aboard our 35’ Donzi center console for a private Cayman Islands adventure built entirely around you. A spacious layout, premium sound system, comfortable seating,...

3 hours Free Cancellation

4.9 (26)

from
$900

Samana Full-Day Tour with Whale Watching and Horse Riding

Visits for Sanctuary of the Humpback Whales in Samana is free. It is available only during the period from January 15, to March 30 of …More

Punta Cana, Dominican Republic

4.2 (11)

Samana Full-Day Tour with Whale Watching and Horse Riding

Visits for Sanctuary of the Humpback Whales in Samana is free. It is available only during the period from January 15, to March 30 of...

11 hours Hotel pickup offered Free Cancellation

4.2 (11)

from
$145

Adventure at the Damajagua Waterfalls From Puerto Plata

Damajagua is a natural monument and if you are looking for an exciting and refreshing experience, you can't miss it. You will enjoy 7 of …More

Puerto Plata, Dominican Republic

4.9 (28)

Adventure at the Damajagua Waterfalls From Puerto Plata

Damajagua is a natural monument and if you are looking for an exciting and refreshing experience, you can't miss it. You will enjoy 7 of...

4 hours Hotel pickup offered Free Cancellation

4.9 (28)

from
$45

Zipline Experience: Sentry hill Zip & Flying Dutchman St Maartin

- Learn about the customs, traditions, lifestyle, and stories of St. Maarten - Embark on the Sky Explorer for the approximately 25 minute ride to …More

4.5 (45)

Zipline Experience: Sentry hill Zip & Flying Dutchman St Maartin

- Learn about the customs, traditions, lifestyle, and stories of St. Maarten - Embark on the Sky Explorer for the approximately 25 minute ride to...

3 hours 27 minutes Free Cancellation

4.5 (45)

from
$129

Blue Hole and Dunn's River Falls Tour from Montego Bay

We start your shore excursion with pickup directly from the Montego Bay Cruise Port or hotel lobby. A relaxing ride in a minivan takes you …More

Montego Bay, Jamaica

5.0 (23)

Blue Hole and Dunn's River Falls Tour from Montego Bay

We start your shore excursion with pickup directly from the Montego Bay Cruise Port or hotel lobby. A relaxing ride in a minivan takes you...

8 hours Hotel pickup offered Free Cancellation

5.0 (23)

from
$151

Tiki Pon Da Sea Cruise to Booby Cay with Lunch from Negril

Plan a cruise to the Booby Cay Island from the 7 mile beach in Negril and relax on the sea then experience a taste of …More

Negril, Jamaica

4.8 (10)

Tiki Pon Da Sea Cruise to Booby Cay with Lunch from Negril

Plan a cruise to the Booby Cay Island from the 7 mile beach in Negril and relax on the sea then experience a taste of...

3 hours Hotel pickup offered Free Cancellation

4.8 (10)

from
$235

Damajagua Waterfalls & Zipline from Amber Cove & Taino bay

Join us for an authentic Dominican shore excursion designed for cruise ship passengers visiting Puerto Plata. Discover local culture with a visit to a traditional …More

Cabarete, Dominican Republic

5.0 (10)

Damajagua Waterfalls & Zipline from Amber Cove & Taino bay

Join us for an authentic Dominican shore excursion designed for cruise ship passengers visiting Puerto Plata. Discover local culture with a visit to a traditional...

5 hours Hotel pickup offered Free Cancellation

5.0 (10)

from
$120

Travelers searching for the best Blue Hole Ocho Rios tour will find this top-rated waterfall and cliff diving experience in Jamaica delivers nonstop adventure and …More

Runaway Bay, Jamaica

4.8 (30)

Blue Hole Ocho Rios

Travelers searching for the best Blue Hole Ocho Rios tour will find this top-rated waterfall and cliff diving experience in Jamaica delivers nonstop adventure and...

2 to 3 hours Hotel pickup offered Free Cancellation

4.8 (30)

from
$63

Zipline, River Tubing and Blue Hole Adventure from Ocho Rios

Plan a visit to the scenic tropical Parish of St. Ann, Jamaica where your adventure will take you on an exhilarating experience flying through the …More

Ocho Rios, Jamaica

5.0 (5)

Zipline, River Tubing and Blue Hole Adventure from Ocho Rios

Plan a visit to the scenic tropical Parish of St. Ann, Jamaica where your adventure will take you on an exhilarating experience flying through the...

5 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$166

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?