Top Caribbean Private Sightseeing Tours

Q: Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Caribbean Private Sightseeing Tours with Instant Confirmation include: Half-Day Buggy Tour to Cave, Macao Beach, and Local Farm Pirate Jeep Sightseeing Adventure! Nassau ATV Buggy Guided Tour Beach Stop Port Hotel Pickup Samples Buggy Tour in Punta Cana with Stops at the Beach and a Cave St.Kitts See It All The Local Behind The Scenes Tour Of St. Kitts View all Tours with Instant Confirmation →

Q: I need a ride! Which Caribbean Private Sightseeing Tours have Hotel Pickup?

No problem. These Caribbean Private Sightseeing Tours include Hotel Pickup: Half-Day Buggy Tour to Cave, Macao Beach, and Local Farm Pirate Jeep Sightseeing Adventure! Nassau ATV Buggy Guided Tour Beach Stop Port Hotel Pickup Samples Buggy Tour in Punta Cana with Stops at the Beach and a Cave Private Catamaran Cruise with Slide & unlimited drinks 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 →

Puerto Plata Private Tour: Umbrella St, Rum, Fortress

Discover Puerto Plata like a local on a private and personalized tour designed around your interests. With our experience and local knowledge, we provide friendly, …More

5.0 (102)

Puerto Plata Private Tour: Umbrella St, Rum, Fortress

Discover Puerto Plata like a local on a private and personalized tour designed around your interests. With our experience and local knowledge, we provide friendly,...

3 to 4 hours Free Cancellation

5.0 (102)

from
$55

Explore Montego Bay Jamaica to Negril Beach & Ricks Cafe Sunset

Take a relaxing trip to Negril, enjoying the beautiful serene beaches, laid back atmosphere ,breath taking cliffs and enjoy the sunset at Rick's Cafe. If …More

Lucea, Jamaica

5.0 (102)

Explore Montego Bay Jamaica to Negril Beach & Ricks Cafe Sunset

Take a relaxing trip to Negril, enjoying the beautiful serene beaches, laid back atmosphere ,breath taking cliffs and enjoy the sunset at Rick's Cafe. If...

7 to 9 hours Hotel pickup offered Free Cancellation

5.0 (102)

from
$122

There is no better way to enjoy your visit to the island than being in charge of your own time and not being crammed into …More

5.0 (102)

Island Buggy Excursions

There is no better way to enjoy your visit to the island than being in charge of your own time and not being crammed into...

1 to 8 hours Free Cancellation

5.0 (102)

from
$499

Half-Day Adventure 4x4 ATV, cenote and Macao beach in Punta Cana

This is not just an ATV ride — it's a true Dominican adventure! Our tour combines adrenaline, culture, and nature in one unforgettable package. We …More

Punta Cana, Dominican Republic

5.0 (101)

Half-Day Adventure 4x4 ATV, cenote and Macao beach in Punta Cana

This is not just an ATV ride — it's a true Dominican adventure! Our tour combines adrenaline, culture, and nature in one unforgettable package. We...

4 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (101)

from
$22

Fully flexible Private Saint Lucia Soufriere Tour (Land)

Get ready for the ultimate island adventure where you call the shots! Forget rigid itineraries and cookie-cutter tours, this is pure, unfiltered fun, shaped entirely …More

Soufriere, St Lucia

4.8 (99)

Fully flexible Private Saint Lucia Soufriere Tour (Land)

Get ready for the ultimate island adventure where you call the shots! Forget rigid itineraries and cookie-cutter tours, this is pure, unfiltered fun, shaped entirely...

6 to 8 hours Hotel pickup offered Free Cancellation

4.8 (99)

from
$130

Welcome to the most unique and exhilarating tour in Aruba. Picture yourself driving your own trike around the stunning island feeling the warm Caribbean breeze. …More

4.8 (97)

Guided Trikes Tour Around Aruba Island

Welcome to the most unique and exhilarating tour in Aruba. Picture yourself driving your own trike around the stunning island feeling the warm Caribbean breeze....

180 to 185 minutes Hotel pickup offered Free Cancellation

4.8 (97)

from
$95

Private St. George's Bermuda History Walking Tour

Explore historic St. George's on a private 2.5-hour walking tour designed exclusively for your group. Discover the streets, churches, museums and landmarks of this UNESCO …More

5.0 (97)

Private St. George's Bermuda History Walking Tour

Explore historic St. George's on a private 2.5-hour walking tour designed exclusively for your group. Discover the streets, churches, museums and landmarks of this UNESCO...

2 hours 30 minutes Free Cancellation

5.0 (97)

from
$81

Concrete Jungle to the Actual Jungle, The Complete Package Tour

In this tour, you will get more value as you experience a city tour, beach tour, cave tour, and rainforest tour all in one. Explore …More

Isla Verde, Puerto Rico

5.0 (97)

Concrete Jungle to the Actual Jungle, The Complete Package Tour

In this tour, you will get more value as you experience a city tour, beach tour, cave tour, and rainforest tour all in one. Explore...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (97)

from
$280

Private boat trip with guide on the most beautiful lagoon of Guadeloupe

Let yourself be guided into the wild world of a mystical river, then explore the mangrove, an original Ecosystem between sea and rivers, in the …More

Basse-Terre Island, Guadeloupe

4.9 (96)

Private boat trip with guide on the most beautiful lagoon of Guadeloupe

Let yourself be guided into the wild world of a mystical river, then explore the mangrove, an original Ecosystem between sea and rivers, in the...

4 hours 30 minutes Free Cancellation

4.9 (96)

from
$673

Enjoy all the beautiful beaches the Virgin Islands has to offer in the comfort and shade of a specifically charter designed boat with reclining bow …More

4.9 (96)

USVI Private Boat Charter Adventure

Enjoy all the beautiful beaches the Virgin Islands has to offer in the comfort and shade of a specifically charter designed boat with reclining bow...

8 hours Free Cancellation

4.9 (96)

from
$1,500

Ocho Rios For A Day / Private Customizable Tours / Jamaica Dream Vacation

This tour option gives our clients an extra ordinary experience by being able to customize their day to suite their interests and needs not to …More

Runaway Bay, Jamaica

4.9 (95)

Ocho Rios For A Day / Private Customizable Tours / Jamaica Dream Vacation

This tour option gives our clients an extra ordinary experience by being able to customize their day to suite their interests and needs not to...

5 to 6 hours Hotel pickup offered Free Cancellation

4.9 (95)

from
$50

Private Party Boat Cruise: Sound System, Open Bar, Natural Pool

Set sail aboard a double-decker catamaran in the Caribbean Sea, beginning with hotel pickup in Punta Cana in the morning or afternoon. Snorkel in crystal …More

Punta Cana, Dominican Republic

5.0 (95)

Private Party Boat Cruise: Sound System, Open Bar, Natural Pool

Set sail aboard a double-decker catamaran in the Caribbean Sea, beginning with hotel pickup in Punta Cana in the morning or afternoon. Snorkel in crystal...

3 hours Hotel pickup offered Free Cancellation

5.0 (95)

from
$745

Exceptional service, complimentary drinks, reliable and trusted drivers where safety is our priority for all tours. …More

Soufriere, St Lucia

4.9 (94)

Soufriere Private Tour

Exceptional service, complimentary drinks, reliable and trusted drivers where safety is our priority for all tours....

5 to 6 hours Hotel pickup offered Free Cancellation

4.9 (94)

from
$95

Private Party Boat with Slide and chicken skewers at Punta Cana

Pink Cat Punta Cana offers a variety of tours, from fishing to party boats, with a crew that has over 25 years of experience. We’ve …More

5.0 (94)

Private Party Boat with Slide and chicken skewers at Punta Cana

Pink Cat Punta Cana offers a variety of tours, from fishing to party boats, with a crew that has over 25 years of experience. We’ve...

3 hours Hotel pickup offered Free Cancellation

5.0 (94)

from
$750

Half-Day Private Stingray City Charter in Cayman Islands

This is a private tour/activity. Only your group will participate. Avoid the crowds of Stingray City aboard your own private, 11-passenger boat. Depart from the …More

Grand Cayman, Cayman Islands

4.9 (94)

Half-Day Private Stingray City Charter in Cayman Islands

This is a private tour/activity. Only your group will participate. Avoid the crowds of Stingray City aboard your own private, 11-passenger boat. Depart from the...

3 hours 30 minutes Free Cancellation

4.9 (94)

from
$625

Full Day Nature Lovers-Cave, Waterfall & Beach Combo

This full-day trip includes 2 destinations away from the usual tourist crowds of San Juan and El Yunque. Enjoy the breath taking views of Cueva …More

4.9 (93)

Full Day Nature Lovers-Cave, Waterfall & Beach Combo

This full-day trip includes 2 destinations away from the usual tourist crowds of San Juan and El Yunque. Enjoy the breath taking views of Cueva...

6 to 7 hours Hotel pickup offered Free Cancellation

4.9 (93)

from
$155

Private Speed Boat Charter in St Maarten & Nature Reserve

Board on a premium style speed boat for a private day charter around St Martin/St Maarten! You can fully personalize your day and do exactly …More

5.0 (92)

Private Speed Boat Charter in St Maarten & Nature Reserve

Board on a premium style speed boat for a private day charter around St Martin/St Maarten! You can fully personalize your day and do exactly...

3 to 7 hours Free Cancellation

5.0 (92)

from
$104

A private boat ride is the best way to enjoy the clear water and beautiful coastline of Aruba with family and/or friends. It will surely …More

4.9 (92)

Private Boat Cruise with Snorkeling

A private boat ride is the best way to enjoy the clear water and beautiful coastline of Aruba with family and/or friends. It will surely...

1 to 4 hours Free Cancellation

4.9 (92)

from
$199

Bamboo Rafting Adventure with Limestone Massage from Montego Bay

We make sure our travels are secure and safe, dive into the beautiful hills of Montego Bay where we ensure a comfortable journey into nature …More

Lucea, Jamaica

4.8 (92)

Bamboo Rafting Adventure with Limestone Massage from Montego Bay

We make sure our travels are secure and safe, dive into the beautiful hills of Montego Bay where we ensure a comfortable journey into nature...

1 hour 30 minutes Hotel pickup offered Free Cancellation

4.8 (92)

from
$55

YS Falls, Black River Safari, Appleton Rum Tour OR Pelican Bar (Choose Up to 3)

PRIVATE TOUR. [Choose Up to 3 ATTRACTIONS] Take a tour down to the South Coast of Jamaica and explore its natural beauty on a private …More

Lucea, Jamaica

4.9 (92)

YS Falls, Black River Safari, Appleton Rum Tour OR Pelican Bar (Choose Up to 3)

PRIVATE TOUR. [Choose Up to 3 ATTRACTIONS] Take a tour down to the South Coast of Jamaica and explore its natural beauty on a private...

6 to 8 hours Hotel pickup offered Free Cancellation

4.9 (92)

from
$195

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Caribbean Private Sightseeing Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Caribbean Private Sightseeing Tours are:

What are the best kid-friendly options for Caribbean Private Sightseeing Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean Private Sightseeing Tours are:

View all kid-friendly Tours →

Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Which Caribbean Private Sightseeing Tours have Free Cancellation?

Caribbean Private Sightseeing Tours 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 Private Sightseeing Tours have Hotel Pickup?

Got any more Caribbean trip ideas?

What are the most popular styles of Tours and Activities in Caribbean?