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 →

Port Royal Heritage & Sightseeing Tour from Kingston

Immerse yourself in the history and culture of Port Royal during this 1.5-hour heritage tour from Kingston. Once the busiest city in the Caribbean, Port …More

Kingston, Jamaica

4.3 (4)

Port Royal Heritage & Sightseeing Tour from Kingston

Immerse yourself in the history and culture of Port Royal during this 1.5-hour heritage tour from Kingston. Once the busiest city in the Caribbean, Port...

3 hours Hotel pickup offered Free Cancellation

4.3 (4)

from
$88

Full Day Saint Thomas Private Group Excursion

A customized sightseeing tour with us is the way to go as you can customize your tour to what you want for you and your …More

Cruz Bay, US Virgin Islands

4.0 (4)

Full Day Saint Thomas Private Group Excursion

A customized sightseeing tour with us is the way to go as you can customize your tour to what you want for you and your...

5 to 7 hours Hotel pickup offered Free Cancellation

4.0 (4)

from
$1,295

Full-Day Private Cruise in Turks and Caicos with Lunch

Come discover with us many different islands and cays in the Caicos islands where the waters are crystal clear and you can swim and snorkel. …More

4.3 (4)

Full-Day Private Cruise in Turks and Caicos with Lunch

Come discover with us many different islands and cays in the Caicos islands where the waters are crystal clear and you can swim and snorkel....

8 hours Hotel pickup offered Free Cancellation

4.3 (4)

from
$2,700

This is a very unique Tour mainly because our Guest are able to customize it, Our guest gets the privilege of deciding where and how …More

4.3 (4)

St Maarten Sensation Island Tour

This is a very unique Tour mainly because our Guest are able to customize it, Our guest gets the privilege of deciding where and how...

5 to 6 hours Hotel pickup offered Free Cancellation

4.3 (4)

from
$65

Private Tour of Bob Marley House from Ocho Rios

Bob Marley tour gives travelers a chance to live the life of the legend and icon of reggae music. Experience the adventure of driving through …More

Ocho Rios, Jamaica

4.3 (4)

Private Tour of Bob Marley House from Ocho Rios

Bob Marley tour gives travelers a chance to live the life of the legend and icon of reggae music. Experience the adventure of driving through...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.3 (4)

from
$95

Clear Kayak Photoshoot in Montego Bay (Single)

Indulge in a mesmerizing Clear Kayak Photoshoot at one of Jamaica's hidden gems – a stunning, tranquil beach. Our seasoned team and skilled photographers ensure …More

Trelawny, Jamaica

4.3 (4)

Clear Kayak Photoshoot in Montego Bay (Single)

Indulge in a mesmerizing Clear Kayak Photoshoot at one of Jamaica's hidden gems – a stunning, tranquil beach. Our seasoned team and skilled photographers ensure...

1 to 2 hours Hotel pickup offered Free Cancellation

4.3 (4)

from
$198

San Juan’s Historic Streets Audio Guided Walking Tour

Go at your own pace, anytime, on this location-aware, smartphone-guided historic San Juan walking tour. On our historic adventure, you will walk the cobblestone streets …More

4.0 (4)

San Juan’s Historic Streets Audio Guided Walking Tour

Go at your own pace, anytime, on this location-aware, smartphone-guided historic San Juan walking tour. On our historic adventure, you will walk the cobblestone streets...

55 to 75 minutes Free Cancellation

4.0 (4)

from
$12

The fact that you can have a flying dress princess photoshoot at one of the most beautiful island in the Caribbean. A mix of Sumptuousness …More

Montego Bay, Jamaica

4.3 (4)

Flying Dress Photoshoot in Jamaica

The fact that you can have a flying dress princess photoshoot at one of the most beautiful island in the Caribbean. A mix of Sumptuousness...

1 hour Free Cancellation

4.3 (4)

from
$250

Blue Hole and River Tubing from Ocho Rios

Relax and immerse yourself in the stunning natural beauty of hidden Jamaica as we set off on this nature excursion. Your adventure kicks off right …More

Kingston, Jamaica

4.0 (4)

Blue Hole and River Tubing from Ocho Rios

Relax and immerse yourself in the stunning natural beauty of hidden Jamaica as we set off on this nature excursion. Your adventure kicks off right...

5 hours Hotel pickup offered Free Cancellation

4.0 (4)

from
$140

Safari Tour – Paradisiacal Excursion to Bahía de las Águilas

Get to know one of the beaches with the most crystal clear water in the world and one of the most beautiful in the Dominican …More

4.0 (4)

Safari Tour – Paradisiacal Excursion to Bahía de las Águilas

Get to know one of the beaches with the most crystal clear water in the world and one of the most beautiful in the Dominican...

4 hours Free Cancellation

4.0 (4)

from
$100

From Santo Domingo: Paradise Beach VIP Private All-Inclusive Tour

This Full Day VIP from Santo Domingo stands out for being the most comfortable, safe and direct way to visit Bahía de las Águilas. We …More

Santo Domingo, Dominican Republic

4.3 (4)

From Santo Domingo: Paradise Beach VIP Private All-Inclusive Tour

This Full Day VIP from Santo Domingo stands out for being the most comfortable, safe and direct way to visit Bahía de las Águilas. We...

12 to 14 hours Hotel pickup offered Free Cancellation

4.3 (4)

from
$199

Enjoy a 2 to 4-hour private wildlife tour on a 23ft boat. Observe diverse wildlife, including birds, manatees, caimans, and turtles, while cruising in 100% …More

4.3 (4)

Backwater Wildlife and Boat Tour

Enjoy a 2 to 4-hour private wildlife tour on a 23ft boat. Observe diverse wildlife, including birds, manatees, caimans, and turtles, while cruising in 100%...

2 to 4 hours Free Cancellation

4.3 (4)

from
$330

Bob Marley's Nine Mile Guided Full Day Tour from Montego Bay

Follow the rhythm of reggae through the lush hills of St. Ann as you journey to 9 Mile, the legendary birthplace and resting place of …More

Montego Bay, Jamaica

4.0 (4)

Bob Marley's Nine Mile Guided Full Day Tour from Montego Bay

Follow the rhythm of reggae through the lush hills of St. Ann as you journey to 9 Mile, the legendary birthplace and resting place of...

3 to 4 hours Hotel pickup offered Free Cancellation

4.0 (4)

from
$150

No others will join your group. You can plan your own itenerary what you'd like. Others don't have to wait for you and you don't …More

4.0 (3)

Private Tour of Bonaire

No others will join your group. You can plan your own itenerary what you'd like. Others don't have to wait for you and you don't...

3 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$450

Punta Cana Caribbean Private Party Cruise

If you are looking for a private tour for family, bachelor party, wedding celebration, . Book your private group to escape! You call the shots. …More

Punta Cana, Dominican Republic

4.0 (3)

Punta Cana Caribbean Private Party Cruise

If you are looking for a private tour for family, bachelor party, wedding celebration, . Book your private group to escape! You call the shots....

3 hours Free Cancellation

4.0 (3)

from
$925

Mystic Mountain Canopy Experience From Montego Bay

From the Sky Explorer Chairlift (Aerial) Mystic Mountain Canopy Experience Jamaica which made up of state-of-the-art chairlifts that soars above the treetops on a breathtaking …More

Montego Bay, Jamaica

4.0 (3)

Mystic Mountain Canopy Experience From Montego Bay

From the Sky Explorer Chairlift (Aerial) Mystic Mountain Canopy Experience Jamaica which made up of state-of-the-art chairlifts that soars above the treetops on a breathtaking...

5 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$231

This is a great opportunity for persons who want to learn about Jamaica's rich history and culture. This tour is extremely unique because it's very …More

Trelawny, Jamaica

4.0 (3)

Kingston & Blue Mountain Adventure

This is a great opportunity for persons who want to learn about Jamaica's rich history and culture. This tour is extremely unique because it's very...

12 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$180

Fort Charlotte, Botanical Gardens and Kingstown Tours with Detention Tours

Visiting the oldest Garden in the Western Hemisphere. - Visiting two of the oldest church on the island - Driving/walking through the capital Kingstown getting …More

Kingstown, St Vincent and the Grenadines

4.0 (3)

Fort Charlotte, Botanical Gardens and Kingstown Tours with Detention Tours

Visiting the oldest Garden in the Western Hemisphere. - Visiting two of the oldest church on the island - Driving/walking through the capital Kingstown getting...

1 to 2 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$41

In the company of our experience, knowledgeable, friendly and certified driver you will enjoy the ride and the stops at the different shopping area. No …More

Choc, St Lucia

4.0 (3)

Shopping - St Lucia Got Talent Tour

In the company of our experience, knowledgeable, friendly and certified driver you will enjoy the ride and the stops at the different shopping area. No...

2 to 3 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$60

Private Dunns River Falls and Bamboo Beach Club Tour from Grand Palladium

Immerse yourself in the natural beauty of Dunn's River Falls in Ocho Rios, Jamaica, a renowned must-see attraction that captivates visitors with its breathtaking scenery. …More

Lucea, Jamaica

4.0 (3)

Private Dunns River Falls and Bamboo Beach Club Tour from Grand Palladium

Immerse yourself in the natural beauty of Dunn's River Falls in Ocho Rios, Jamaica, a renowned must-see attraction that captivates visitors with its breathtaking scenery....

8 hours 30 minutes Hotel pickup offered Free Cancellation

4.0 (3)

from
$109

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?