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 →

Montego Bay Appleton Estate and Pelican Bar Tour

Travel the beautiful southcoast of Jamaica. This is a two hours drive tour that takes you through three Parishes in the heart of Jamaica, where …More

Lucea, Barbados

4.7 (14)

Montego Bay Appleton Estate and Pelican Bar Tour

Travel the beautiful southcoast of Jamaica. This is a two hours drive tour that takes you through three Parishes in the heart of Jamaica, where...

8 hours Hotel pickup offered Free Cancellation

4.7 (14)

from
$120

Welcoming you to our beautiful Island of St Lucia, we will see to it that your day is well spent and will have you thinking …More

Marigot Bay, St Lucia

4.4 (14)

Private Soufriere Experience Tour

Welcoming you to our beautiful Island of St Lucia, we will see to it that your day is well spent and will have you thinking...

2 to 5 hours Hotel pickup offered Free Cancellation

4.4 (14)

from
$90

Private Tour to the East Side of Puerto Rico

At Paraiso PR, we strongly believe that the best way to experience a new place is to see through your own eyes. Our mission is …More

Fajardo, Puerto Rico

4.3 (13)

Private Tour to the East Side of Puerto Rico

At Paraiso PR, we strongly believe that the best way to experience a new place is to see through your own eyes. Our mission is...

5 to 8 hours Hotel pickup offered Free Cancellation

4.3 (13)

from
$95

Private Higuey Cultural Tour from Punta Cana (Half-day)

Come along with us to discover the closed city from Punta Cana! Higüey city, Head city of La Altagracia Province. The tour starts by taking …More

Punta Cana, Dominican Republic

4.7 (13)

Private Higuey Cultural Tour from Punta Cana (Half-day)

Come along with us to discover the closed city from Punta Cana! Higüey city, Head city of La Altagracia Province. The tour starts by taking...

5 hours Free Cancellation

4.7 (13)

from
$275

Horseback riding tour buy the beach or countryside port silver

What Makes Our Beach Horseback Riding Tour Unique? 1. Personalized service: You’re not just another tourist. Our friendly guides take the time to connect with …More

Puerto Plata, Dominican Republic

4.6 (13)

Horseback riding tour buy the beach or countryside port silver

What Makes Our Beach Horseback Riding Tour Unique? 1. Personalized service: You’re not just another tourist. Our friendly guides take the time to connect with...

3 hours Hotel pickup offered Free Cancellation

4.6 (13)

from
$80

Full-Day Private Cruise in Cayo Caracoles

Enjoy the luxury of your own private boat in the pristine waters of La Parguera. You will never forget your day in Cayo Caracoles or …More

4.7 (13)

Full-Day Private Cruise in Cayo Caracoles

Enjoy the luxury of your own private boat in the pristine waters of La Parguera. You will never forget your day in Cayo Caracoles or...

4 hours Free Cancellation

4.7 (13)

from
$500

Island Chauffeur Taxi Tour provides dependable customized tours, prioritizing comfort and a hassle-free experience travelers. Our dedicated team aims to help guest relax and appreciate …More

Soufriere, St Lucia

4.5 (13)

Private Island Tour St. Lucia

Island Chauffeur Taxi Tour provides dependable customized tours, prioritizing comfort and a hassle-free experience travelers. Our dedicated team aims to help guest relax and appreciate...

3 to 4 hours Hotel pickup offered Free Cancellation

4.5 (13)

from
$110

Rockland Bird Sanctuary Tour with Transportation Hotel Pick-Up

The Rockland Bird Sanctuary is home to many species of birds, some endemic to Jamaica while others flew to the Island from other countries and …More

Montego Bay, Jamaica

4.5 (13)

Rockland Bird Sanctuary Tour with Transportation Hotel Pick-Up

The Rockland Bird Sanctuary is home to many species of birds, some endemic to Jamaica while others flew to the Island from other countries and...

1 to 3 hours Hotel pickup offered Free Cancellation

4.5 (13)

from
$49

Sightseeing Tour of Montego Bay City w/ Options to Personalize

Experience a deeper look into the city of Montego Bay from this tour journey. Learn of its history and feel the vibe of the toursim …More

Montego Bay, Jamaica

4.7 (13)

Sightseeing Tour of Montego Bay City w/ Options to Personalize

Experience a deeper look into the city of Montego Bay from this tour journey. Learn of its history and feel the vibe of the toursim...

2 to 3 hours Hotel pickup offered Free Cancellation

4.7 (13)

from
$44

Private Tour in Miches with La Jarda Waterfall Experience

The tour starts at Magua Community where we will have meet the local hiking guides to hike to the National Park Salto de La Jalda, …More

4.7 (13)

Private Tour in Miches with La Jarda Waterfall Experience

The tour starts at Magua Community where we will have meet the local hiking guides to hike to the National Park Salto de La Jalda,...

10 hours 12 minutes Free Cancellation

4.7 (13)

from
$180

Puerto Plata Challenge: City Tour & 7 Waterfalls of Damajagua

This private tour is much more than just an excursion; it is an experience that takes us to know nature in its purest form, we …More

Puerto Plata, Dominican Republic

4.6 (13)

Puerto Plata Challenge: City Tour & 7 Waterfalls of Damajagua

This private tour is much more than just an excursion; it is an experience that takes us to know nature in its purest form, we...

4 to 5 hours Hotel pickup offered Free Cancellation

4.6 (13)

from
$83

St Thomas Half Day Private Tour (1-10 ppl)

This tour caters to your group only. You get a vehicle just for your group for the whole day. It offers the flexibility of choosing …More

Cruz Bay, US Virgin Islands

4.6 (12)

St Thomas Half Day Private Tour (1-10 ppl)

This tour caters to your group only. You get a vehicle just for your group for the whole day. It offers the flexibility of choosing...

4 hours Hotel pickup offered Free Cancellation

4.6 (12)

from
$850

Private Bahamas Half-Day Fishing Tour from New Providence

Depart Paradise Island on a comfortable 32ft Luhrs. Enjoy a short 20 minute ride where you can begin to set out your lines. You can …More

4.4 (12)

Private Bahamas Half-Day Fishing Tour from New Providence

Depart Paradise Island on a comfortable 32ft Luhrs. Enjoy a short 20 minute ride where you can begin to set out your lines. You can...

4 hours Free Cancellation

4.4 (12)

from
$925

Enjoy an astonishing Clear Kayak Photoshoot on one of the most beautiful and secluded beaches in Jamaica. Our experience and professional photographers will ensure that …More

Montego Bay, Jamaica

4.4 (12)

Clear Kayak Photoshoot in Montego Bay

Enjoy an astonishing Clear Kayak Photoshoot on one of the most beautiful and secluded beaches in Jamaica. Our experience and professional photographers will ensure that...

1 to 2 hours Hotel pickup offered Free Cancellation

4.4 (12)

from
$170

You can enjoy the Dominican habit, share with local people, learn about their customs, go from store to buy gifts for your friends and family, …More

Punta Cana, Dominican Republic

4.5 (11)

Private City Tours Higüey

You can enjoy the Dominican habit, share with local people, learn about their customs, go from store to buy gifts for your friends and family,...

3 to 4 hours Hotel pickup offered Free Cancellation

4.5 (11)

from
$250

PRIVATE: 3in1 - Los Haitises N.P. + Y. Waterfall + Mount. Redonda

PRIVATE TOUR: You're about to live your best and unique experience of a full day trip exploring Los Haitises National Park, hiking its rainforests used …More

Punta Cana, Dominican Republic

4.6 (11)

PRIVATE: 3in1 - Los Haitises N.P. + Y. Waterfall + Mount. Redonda

PRIVATE TOUR: You're about to live your best and unique experience of a full day trip exploring Los Haitises National Park, hiking its rainforests used...

12 to 14 hours Hotel pickup offered Free Cancellation

4.6 (11)

from
$149

Feel like a million bucks and book your Jamaica Flying Dress Photoshoot with Kevin Wright. Perfect gift for anniversary, birthday, girls trip. Please bring your …More

Montego Bay, Jamaica

4.3 (11)

Jamaica Flying Dress Photoshoots

Feel like a million bucks and book your Jamaica Flying Dress Photoshoot with Kevin Wright. Perfect gift for anniversary, birthday, girls trip. Please bring your...

1 to 2 hours

4.3 (11)

from
$450

Cocoa & Artisan Chocolate Route with an Historical Tour in Puerto Plata City

Experience the Cocoa production process from planting to harvesting. We invite you to enjoy through your senses one of the secrets that surround this great …More

Puerto Plata, Dominican Republic

4.4 (11)

Cocoa & Artisan Chocolate Route with an Historical Tour in Puerto Plata City

Experience the Cocoa production process from planting to harvesting. We invite you to enjoy through your senses one of the secrets that surround this great...

6 hours Hotel pickup offered Free Cancellation

4.4 (11)

from
$98

Full Day Essential Bob Marley Tour Home Visit and More

Immerse yourself in the world of Bob Marley with this private, exclusive tour crafted just for enthusiasts who seek a deeper connection with the music …More

Ocho Rios, Jamaica

4.7 (11)

Full Day Essential Bob Marley Tour Home Visit and More

Immerse yourself in the world of Bob Marley with this private, exclusive tour crafted just for enthusiasts who seek a deeper connection with the music...

8 hours Hotel pickup offered Free Cancellation

4.7 (11)

from
$200

Set sail on an exclusive journey aboard Aqua Symphony, where luxury meets adventure on our 48ft Cranchi Atlantique monohull yacht. Your voyage will whisk you …More

Tortola, British Virgin Islands

4.7 (11)

Full-Day Charter in Tortola British Virgin Islands

Set sail on an exclusive journey aboard Aqua Symphony, where luxury meets adventure on our 48ft Cranchi Atlantique monohull yacht. Your voyage will whisk you...

8 hours Hotel pickup offered Free Cancellation

4.7 (11)

from
$2,600

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?