Top Caribbean Private Sightseeing Tours

Q: Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Caribbean Private Sightseeing Tours with Instant Confirmation include: Private Eleuthera Island: Swim With Pigs, Turtles & Stingrays Private Exuma Cays Day: Iguana, Shark, Pigs, Sandbar & Lunch 5-Day Private Tour in The Bahamas with Pickup Yacht YES DARLING - Private Boat St Martin, St Barth & Anguilla St Martin Gd-Case, Private Romantic Cruise 4 days View all Tours with Instant Confirmation →

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 →

Private Montego Bay Customized Tour with Pickup and Guide

Booking with me means you'll get an authentic Jamaican experience tailored to showcase the best of what my country has to offer. As a local, …More

Trelawny, Jamaica

4.9 (153)

Private Montego Bay Customized Tour with Pickup and Guide

Booking with me means you'll get an authentic Jamaican experience tailored to showcase the best of what my country has to offer. As a local,...

3 hours Hotel pickup offered Free Cancellation

4.9 (153)

from
$65

Negril 7 Miles Beach and Rick's Cafe Tour

Booking your Negril 7 Mile Beach and Rick’s Café tour with Ultimate Excursions Tours and Taxi Service guarantees an unforgettable day filled with beauty, fun, …More

Lucea, Jamaica

5.0 (19)

Negril 7 Miles Beach and Rick's Cafe Tour

Booking your Negril 7 Mile Beach and Rick’s Café tour with Ultimate Excursions Tours and Taxi Service guarantees an unforgettable day filled with beauty, fun,...

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (19)

from
$65

Doctor's Cave Beach, Jimmy Buffett 's Margaritaville and Shopping

Explore the white sand Doctor's Cave Beach, the legendary Margaritaville and stroll along the 'hip-strip' for some shopping during this day trip. With your local …More

Montego Bay, Jamaica

4.5 (29)

Doctor's Cave Beach, Jimmy Buffett 's Margaritaville and Shopping

Explore the white sand Doctor's Cave Beach, the legendary Margaritaville and stroll along the 'hip-strip' for some shopping during this day trip. With your local...

5 hours Hotel pickup offered Free Cancellation

4.5 (29)

from
$65

Bamboo Rafting, Margaritaville & Sightseeing Tour In Ocho Rios

One of the most calming and relaxing experience you can have in Jamaica is rafting on the White River. Located in the parish of St …More

Ocho Rios, Jamaica

5.0 (7)

Bamboo Rafting, Margaritaville & Sightseeing Tour In Ocho Rios

One of the most calming and relaxing experience you can have in Jamaica is rafting on the White River. Located in the parish of St...

3 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$65

Explore Puerto Plata on this half-day tour. Listen to informative and entertaining commentary from your Tour guide, 4 hours visiting local landmarks such as the …More

Puerto Plata, Dominican Republic

5.0 (16)

Puerto Plata City tour

Explore Puerto Plata on this half-day tour. Listen to informative and entertaining commentary from your Tour guide, 4 hours visiting local landmarks such as the...

4 hours 15 minutes Hotel pickup offered Free Cancellation

5.0 (16)

from
$65

Damajagua 7 Waterfalls with Lunch – Swim, Slide & Jump

Get ready to hike, swim, slide and jump through Damajagua’s spectacular 7 waterfalls! Explore lush tropical trails with an experienced local guide before reaching natural …More

Puerto Plata, Dominican Republic

5.0 (11)

Damajagua 7 Waterfalls with Lunch – Swim, Slide & Jump

Get ready to hike, swim, slide and jump through Damajagua’s spectacular 7 waterfalls! Explore lush tropical trails with an experienced local guide before reaching natural...

3 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$65

San Juan Urban Art Bike Tour 2 Hour and 4 Hour Options

Discover the vibrant street art of San Juan on a guided bike tour through Santurce or Río Piedras. Experience the city's rich culture and history …More

5.0 (13)

San Juan Urban Art Bike Tour 2 Hour and 4 Hour Options

Discover the vibrant street art of San Juan on a guided bike tour through Santurce or Río Piedras. Experience the city's rich culture and history...

1 to 2 hours Free Cancellation

5.0 (13)

from
$65

Half Day Tour in Aruba with Guide (Min 6 / Max 10 persons)

Tour guests will enjoy the unique tales of Aruba as told by our professional guide. You'll get to enjoy and learn all about some of …More

5.0 (1)

Half Day Tour in Aruba with Guide (Min 6 / Max 10 persons)

Tour guests will enjoy the unique tales of Aruba as told by our professional guide. You'll get to enjoy and learn all about some of...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$65

Party Boat Booze Cruise - Crucero con bebidas y Fiesta en Barco

Enjoy views of the Dominican Republic's east coast aboard a catamaran cruise from Punta Cana. Relax on board the boat and sip drinks from the …More

5.0 (5)

Party Boat Booze Cruise - Crucero con bebidas y Fiesta en Barco

Enjoy views of the Dominican Republic's east coast aboard a catamaran cruise from Punta Cana. Relax on board the boat and sip drinks from the...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (5)

from
$65

Luminous Lagoon (Glistening Waters) Night Tour

Take a boat out on the glowing waters of the Luminous Lagoon and jump in for a swim among the harmless phosphorescent phytoplankton. Enjoy the …More

4.7 (10)

Luminous Lagoon (Glistening Waters) Night Tour

Take a boat out on the glowing waters of the Luminous Lagoon and jump in for a swim among the harmless phosphorescent phytoplankton. Enjoy the...

2 to 3 hours Hotel pickup offered Free Cancellation

4.7 (10)

from
$65

A serene stop at the Blue Hole on this half-day private tour from Ocho Rios. With a private guide dedicated just to you and your …More

Kingston, Jamaica

5.0 (6)

Blue Hole Adventure Tours

A serene stop at the Blue Hole on this half-day private tour from Ocho Rios. With a private guide dedicated just to you and your...

1 hour 30 minutes Hotel pickup offered Free Cancellation

5.0 (6)

from
$65

Private Countryside and City Tour in Puerto Plata

This tour will take you to discover the rich culture, delicious cuisine and stunning landscapes of this beautiful city. We focus on learning more about …More

Puerto Plata, Dominican Republic

4.8 (8)

Private Countryside and City Tour in Puerto Plata

This tour will take you to discover the rich culture, delicious cuisine and stunning landscapes of this beautiful city. We focus on learning more about...

3 to 4 hours Hotel pickup offered Free Cancellation

4.8 (8)

from
$65

The Montreal Garden Tour with Fraser's Taxi and Tours

Our guest are treated to a breathtaking Eco-tour of the pristine Montreal Gardens nestled deep in the Mesopotamia (Marriaqua) valley. Each guest would be treated …More

Kingstown, St Vincent and the Grenadines

5.0 (8)

The Montreal Garden Tour with Fraser's Taxi and Tours

Our guest are treated to a breathtaking Eco-tour of the pristine Montreal Gardens nestled deep in the Mesopotamia (Marriaqua) valley. Each guest would be treated...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$65

7 Damajagua waterfalls and typical Dominican lunch

The Damajagua Waterfalls begin with a 20-minute walk past bridges, forest and flora, before reaching the waterfall number 7, then begin to descend either by …More

Puerto Plata, Dominican Republic

5.0 (5)

7 Damajagua waterfalls and typical Dominican lunch

The Damajagua Waterfalls begin with a 20-minute walk past bridges, forest and flora, before reaching the waterfall number 7, then begin to descend either by...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$65

Falmouth Shore Excursion: Private Montego Bay City Tour

Take a private, guided-tour through the city of Montego Bay. You will visit historical sites and learn about the history of Jamaica. This is the …More

Trelawny, Jamaica

5.0 (2)

Falmouth Shore Excursion: Private Montego Bay City Tour

Take a private, guided-tour through the city of Montego Bay. You will visit historical sites and learn about the history of Jamaica. This is the...

4 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$65

Private Luminous Lagoon Tour from Montego Bay

We give outstanding customer services and we are not afraid to go above and beyond for our clients to ensure that they are happy and …More

Trelawny, Jamaica

5.0 (4)

Private Luminous Lagoon Tour from Montego Bay

We give outstanding customer services and we are not afraid to go above and beyond for our clients to ensure that they are happy and...

3 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$65

Private River Rafting with Limestone Massage & ATV at Montego Bay

This is a 3-pack combo of Great River Rafting, Limestone Massage, and ATV. With a certified guide, you can learn about Jamaica’s history and sites. …More

Montego Bay, Jamaica

5.0 (1)

Private River Rafting with Limestone Massage & ATV at Montego Bay

This is a 3-pack combo of Great River Rafting, Limestone Massage, and ATV. With a certified guide, you can learn about Jamaica’s history and sites....

2 to 3 hours Free Cancellation

5.0 (1)

from
$65

Montego Bay Private Clubbing Experience with Transportation

We offer a hassle-free experience by taking care of all your transportation needs, allowing you to fully enjoy Montego Bay's vibrant nightlife scene without any …More

Montego Bay, Jamaica

4.4 (7)

Montego Bay Private Clubbing Experience with Transportation

We offer a hassle-free experience by taking care of all your transportation needs, allowing you to fully enjoy Montego Bay's vibrant nightlife scene without any...

3 hours 45 minutes Hotel pickup offered Free Cancellation

4.4 (7)

from
$65

1 Hour Private Rafting Experience in Jamaica

Rafting on the White River is a tour to experience while enjoying the beautiful island of Jamaica. The tour is carried out by a raft …More

Ocho Rios, Jamaica

4.7 (9)

1 Hour Private Rafting Experience in Jamaica

Rafting on the White River is a tour to experience while enjoying the beautiful island of Jamaica. The tour is carried out by a raft...

45 to 60 minutes Free Cancellation

4.7 (9)

from
$65

Jamaica: Negril Seven Mile Beach Private Full-Day Tour

If you want to enjoy Scrumptious local fresh sea food and visit Negril Jamaica , this is the perfect experience for you. Our exclusive tour …More

Montego Bay, Jamaica

5.0 (3)

Jamaica: Negril Seven Mile Beach Private Full-Day Tour

If you want to enjoy Scrumptious local fresh sea food and visit Negril Jamaica , this is the perfect experience for you. Our exclusive tour...

6 to 7 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$65

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?

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?

No problem. These Caribbean Private Sightseeing Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Caribbean trip ideas?

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