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 →

Dwight Harvey Tours ensure the best and most anticipated tour taking you to your destination in Negril. Visitors will get to experience their vacation of …More

Lucea, Jamaica

5.0 (4)

Negril Beach & Rick's Cafe Tour

Dwight Harvey Tours ensure the best and most anticipated tour taking you to your destination in Negril. Visitors will get to experience their vacation of...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$40

We will Greet you at our meeting point. From there, the tour will proceed to what is considered the island’s national monument, the Berkeley Memorial. …More

4.1 (9)

Panoramic Sightseeing Tour of St Kitts

We will Greet you at our meeting point. From there, the tour will proceed to what is considered the island’s national monument, the Berkeley Memorial....

2 hours Free Cancellation

4.1 (9)

from
$40

Travel in the steps of Captain Jack Sparrow to the film location of the Pirates of the Caribbean. See beaches, local bars, and more on …More

Kingstown, St Vincent and the Grenadines

5.0 (2)

Half-Day Pirates Tour from Kingstown

Travel in the steps of Captain Jack Sparrow to the film location of the Pirates of the Caribbean. See beaches, local bars, and more on...

3 to 5 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$40

Montego Bay Highlight Tour Visit local Community And See Local Stuffs

Trust Tours Jamaica guarantee the best and most anticipated tour journey, taking on some of the top destination spots such as the city of Montego Bay …More

Montego Bay, Jamaica

4.8 (4)

Montego Bay Highlight Tour Visit local Community And See Local Stuffs

Trust Tours Jamaica guarantee the best and most anticipated tour journey, taking on some of the top destination spots such as the city of Montego Bay...

2 to 3 hours Hotel pickup offered Free Cancellation

4.8 (4)

from
$40

Ambar Chocolate Puerto Plata Culture and Colored Umbrella

Discover the vibrant soul of Puerto Plata in a cultural tour that will delight its five senses. This tour takes it beyond the beaches to …More

Puerto Plata, Dominican Republic

5.0 (3)

Ambar Chocolate Puerto Plata Culture and Colored Umbrella

Discover the vibrant soul of Puerto Plata in a cultural tour that will delight its five senses. This tour takes it beyond the beaches to...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$40

Bamboo Rafting, Limestone Massage and Hip Strip Tour In Jamaica

Relax and take in the scenery. You’ll be surrounded by beautiful trees and exquisite wildlife. No worries though, none of the wildlife in this area …More

Montego Bay, Jamaica

3.7 (10)

Bamboo Rafting, Limestone Massage and Hip Strip Tour In Jamaica

Relax and take in the scenery. You’ll be surrounded by beautiful trees and exquisite wildlife. No worries though, none of the wildlife in this area...

3 hours Hotel pickup offered Free Cancellation

3.7 (10)

from
$40

River Rafting and River Tubing Transportation Only

River Rafting and River Tubing is a combo tour that entails natural beauty of the famous white river, this river comes from the hills through …More

Ocho Rios, Jamaica

5.0 (1)

River Rafting and River Tubing Transportation Only

River Rafting and River Tubing is a combo tour that entails natural beauty of the famous white river, this river comes from the hills through...

2 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$40

MBJ Airport Private Transfer to Hotels in the Montego Bay Area.

We provide Private Airport Transportation in Air conditioned vehicles. Our drivers will meet you at the airport with a warm pleasant welcome and your name …More

Montego Bay, Jamaica

5.0 (1)

MBJ Airport Private Transfer to Hotels in the Montego Bay Area.

We provide Private Airport Transportation in Air conditioned vehicles. Our drivers will meet you at the airport with a warm pleasant welcome and your name...

10 to 25 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$40

Unforgettable horseback riding experience in scenic Montego Bay with included round-trip transportation …More

Montego Bay, Jamaica

5.0 (1)

Horseback Riding in Montego Bay

Unforgettable horseback riding experience in scenic Montego Bay with included round-trip transportation...

60 to 80 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$40

Hastings Tours will ensure you have a fun-filled vacation when you book for a relaxing day on the beach. Negril White Sand beach is Jamaica's …More

Lucea, Jamaica

4.7 (3)

Negril Seven Miles Beach & Rick's Cafe

Hastings Tours will ensure you have a fun-filled vacation when you book for a relaxing day on the beach. Negril White Sand beach is Jamaica's...

2 to 3 hours Hotel pickup offered Free Cancellation

4.7 (3)

from
$40

Night Life, Party Vibes & Clubbing in Montego Bay

Montego Bay Nightlife is always popping. Especially with clubs like these that you’ll get a chance to experience from partying with Jamaicans. Smoke hookahs, enjoy …More

Montego Bay, Jamaica

3.0 (2)

Night Life, Party Vibes & Clubbing in Montego Bay

Montego Bay Nightlife is always popping. Especially with clubs like these that you’ll get a chance to experience from partying with Jamaicans. Smoke hookahs, enjoy...

3 to 4 hours Hotel pickup offered Free Cancellation

3.0 (2)

from
$40

Jamaica Giants sculpture park, art galleries

Come visit the land of the Giants-Jamaica's #1 Sculpture Park and art galleries! Have an intimate experience with thousands of acres of unspoiled tropical forests …More

Negril, Jamaica

4.6 (23)

Jamaica Giants sculpture park, art galleries

Come visit the land of the Giants-Jamaica's #1 Sculpture Park and art galleries! Have an intimate experience with thousands of acres of unspoiled tropical forests...

1 to 2 hours Hotel pickup offered Free Cancellation

4.6 (23)

from
$40

Every morning we go out on a 2 tank dive trips by car and we dive more or less all dive sites that are reached from shore. …More

5.0 (128)

2 Tank Guided Shore Dive in Curacao

Every morning we go out on a 2 tank dive trips by car and we dive more or less all dive sites that are reached from shore....

2 to 4 hours Free Cancellation

5.0 (128)

from
$39

This is the most intimate way to experience Castries. Our expert local knowledgeable guides serve as your fun companions. The entire history of St.Lucia revolves …More

4.5 (28)

Castries City Walking Tours

This is the most intimate way to experience Castries. Our expert local knowledgeable guides serve as your fun companions. The entire history of St.Lucia revolves...

90 to 120 minutes Free Cancellation

4.5 (28)

from
$39

Montego Bay Hip Strip Shopping and Margaritaville

Step into luxury and adventure with our private tour of montegobay ! Leave the stress of navigation behind as you relax in your exclusive vehicle …More

Montego Bay, Jamaica

4.5 (8)

Montego Bay Hip Strip Shopping and Margaritaville

Step into luxury and adventure with our private tour of montegobay ! Leave the stress of navigation behind as you relax in your exclusive vehicle...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.5 (8)

from
$39

Montego Bay’s Sightseeing Tour with Options to Customize

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

Montego Bay, Jamaica

5.0 (8)

Montego Bay’s Sightseeing Tour with Options to Customize

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

1 to 6 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$39

Punta Cana: Private Half-Day Dominican Culture Tour

Step outside your resort and discover everyday life in the Dominican Republic on a private half-day tour for all ages. The journey is part of …More

Punta Cana, Dominican Republic

4.8 (55)

Punta Cana: Private Half-Day Dominican Culture Tour

Step outside your resort and discover everyday life in the Dominican Republic on a private half-day tour for all ages. The journey is part of...

4 to 5 hours Hotel pickup offered Free Cancellation

4.8 (55)

from
$39

Design your dream Barbados adventure with a private, fully customizable island tour! Enjoy 3–4 hours of sightseeing with a friendly, professional guide who will work …More

Speightstown, Barbados

4.8 (212)

Private Half Day Barbados Excursion

Design your dream Barbados adventure with a private, fully customizable island tour! Enjoy 3–4 hours of sightseeing with a friendly, professional guide who will work...

4 hours Hotel pickup offered Free Cancellation

4.8 (212)

from
$39

Devon House Tour with Ice Cream from Kingston

Devon House is a heritage site located in Kingston, the new capital city of Jamaica. It was built in the 19th century by Jamaica’s first …More

Kingston, Jamaica

4.3 (3)

Devon House Tour with Ice Cream from Kingston

Devon House is a heritage site located in Kingston, the new capital city of Jamaica. It was built in the 19th century by Jamaica’s first...

2 hours Hotel pickup offered Free Cancellation

4.3 (3)

from
$38

Private Walking Tour of Old San Juan, and the forts

Experience San Juan the best possible way...through a private tour. Focus on what you are most excited about. Learn about the history and the untold …More

4.9 (78)

Private Walking Tour of Old San Juan, and the forts

Experience San Juan the best possible way...through a private tour. Focus on what you are most excited about. Learn about the history and the untold...

2 hours Free Cancellation

4.9 (78)

from
$38

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?