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 →

Enjoy a mouth-watering tour around the town of Falmouth, sampling local specialties and Jamaican street food. As you walk through the downtown area, your guide …More

Trelawny, Jamaica

3.0 (1)

Falmouth Street Eats

Enjoy a mouth-watering tour around the town of Falmouth, sampling local specialties and Jamaican street food. As you walk through the downtown area, your guide...

2 hours Free Cancellation

3.0 (1)

from
$59

9 mile Bob Marley Musoleum Private Day Trip From Montego Bay

If your a true Bob Marley fan, then why not check out his Birth place in nine mile St Ann’s . It’s a long adventurous …More

Montego Bay, Jamaica

3.0 (1)

9 mile Bob Marley Musoleum Private Day Trip From Montego Bay

If your a true Bob Marley fan, then why not check out his Birth place in nine mile St Ann’s . It’s a long adventurous...

2 to 3 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$138

Montaña Redonda is one of the beautiful places you have to visit in the Dominican Republic. It is located in Miches in the Municipality of …More

La Romana, Dominican Republic

2.3 (3)

Tour to Montana Redonda and sunset

Montaña Redonda is one of the beautiful places you have to visit in the Dominican Republic. It is located in Miches in the Municipality of...

4 to 5 hours Hotel pickup offered Free Cancellation

2.3 (3)

from
$130

Beach and Adventure Day at the Beach Club in Cabo Rojo

Discover an authentic tropical paradise in the Caribbean with our exclusive beach club experience in Cabo Rojo. Designed with cruise passengers in mind, this 4-hour …More

2.7 (3)

Beach and Adventure Day at the Beach Club in Cabo Rojo

Discover an authentic tropical paradise in the Caribbean with our exclusive beach club experience in Cabo Rojo. Designed with cruise passengers in mind, this 4-hour...

4 hours Free Cancellation

2.7 (3)

from
$120

Embark on an unforgettable adventure with our captivating St. John Jeep Tour! Journey through the island like a local alongside our knowledgeable guides. Savor the …More

Cruz Bay, US Virgin Islands

2.0 (1)

Private 4WD Tour to Trunk Bay St John

Embark on an unforgettable adventure with our captivating St. John Jeep Tour! Journey through the island like a local alongside our knowledgeable guides. Savor the...

6 hours Hotel pickup offered Free Cancellation

2.0 (1)

from
$495

Catamaran Excursions to Noah’s Ark Beach Club! Discover the ultimate day trip with our exclusive catamaran excursions to Noah’s Ark Beach Club, a tropical oasis …More

Noah's Ark Beach Club Tour on a Private Catamaran

Catamaran Excursions to Noah’s Ark Beach Club! Discover the ultimate day trip with our exclusive catamaran excursions to Noah’s Ark Beach Club, a tropical oasis...

4 hours

from
$2,000

Enjoy our catamaran with unrivalled comfort and privatized, with your family or friends. Enjoy our delicious cocktails and homemade appetizers facing the beauty of the …More

St Martin Grand Case: Private cruise after sunset

Enjoy our catamaran with unrivalled comfort and privatized, with your family or friends. Enjoy our delicious cocktails and homemade appetizers facing the beauty of the...

2 hours 30 minutes Free Cancellation

from
$1,569

Unique in Saint Martin, embark on our private cruise catamaran for you and let yourself be carried away in this romantic and idyllic setting, with …More

St Martin Gd-Case, Private Romantic Cruise 4 days

Unique in Saint Martin, embark on our private cruise catamaran for you and let yourself be carried away in this romantic and idyllic setting, with...

4 days

from
$6,146

Private Catamaran Cruise and Snorkeling in Montego Bay Area

Basically you get this completely private for your group. Mimosas, cold towels, and an onboard DJ set this Montego Bay Private All-inclusive Catamaran Cruise apart …More

Montego Bay, Jamaica

Private Catamaran Cruise and Snorkeling in Montego Bay Area

Basically you get this completely private for your group. Mimosas, cold towels, and an onboard DJ set this Montego Bay Private All-inclusive Catamaran Cruise apart...

3 to 4 hours Hotel pickup offered

from
$3,700

Private Luxury Dinner Sunset Cruise in St. Lucia

Join us for a Private Dinner Sunset Cruise with a Chef onboard to provide a culinary experience that is second to none. We will cruise …More

Choc, St Lucia

Private Luxury Dinner Sunset Cruise in St. Lucia

Join us for a Private Dinner Sunset Cruise with a Chef onboard to provide a culinary experience that is second to none. We will cruise...

3 hours Hotel pickup offered Free Cancellation

from
$1,600

5 Day Package to Santiago and Puerto Plata with Accommodation

Immerse yourself in the Dominican essence with our exclusive 4 nights and 5 days package! Start your adventure in the heart of Santiago de los …More

Puerto Plata, Dominican Republic

5 Day Package to Santiago and Puerto Plata with Accommodation

Immerse yourself in the Dominican essence with our exclusive 4 nights and 5 days package! Start your adventure in the heart of Santiago de los...

5 days Free Cancellation

from
$3,440

Discover the wonderful Constanza, Dominican Republic, with our exciting tour! We include transportation to this mountain paradise and a unique experience in a safari truck. …More

Private Tour in Constanza Dominican Republic for 15 people

Discover the wonderful Constanza, Dominican Republic, with our exciting tour! We include transportation to this mountain paradise and a unique experience in a safari truck....

6 to 7 hours Free Cancellation

from
$1,425

Private Catamaran and Sunset Cruise to Ricks Cafe from Negril

Basically this completely private cruise is family friendly and perfect for small groups and special celebrations such as birthdays, anniversaries ect. We cater for any …More

Negril, Jamaica

Private Catamaran and Sunset Cruise to Ricks Cafe from Negril

Basically this completely private cruise is family friendly and perfect for small groups and special celebrations such as birthdays, anniversaries ect. We cater for any...

4 to 5 hours Hotel pickup offered

from
$4,100

Experience our Private Local Food Tour in San Juan! Embark on a serene journey through the picturesque landscapes of Puerto Rico as you make your …More

Private Local Food Tour in San Juan

Experience our Private Local Food Tour in San Juan! Embark on a serene journey through the picturesque landscapes of Puerto Rico as you make your...

4 hours Hotel pickup offered Free Cancellation

from
$286

Experience our Private Tour to Black Sand Beach in The Southeast of Puerto Rico! Embark on a serene journey through the picturesque landscapes of Puerto …More

Private Tour to Black Sand Beach in The Southeast of Puerto Rico

Experience our Private Tour to Black Sand Beach in The Southeast of Puerto Rico! Embark on a serene journey through the picturesque landscapes of Puerto...

7 hours Hotel pickup offered Free Cancellation

from
$292

Discover the best of Turks & Caicos Islands aboard this catamaran combining luxury and comfort. Ideal to enjoy a day with friends, family or in …More

Private Sunset Tour Catamaran 44 Big Ben

Discover the best of Turks & Caicos Islands aboard this catamaran combining luxury and comfort. Ideal to enjoy a day with friends, family or in...

2 hours Free Cancellation

from
$1,490

Discover the best of Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or in …More

Private Sunset Tour Fjord 38 Ben

Discover the best of Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or in...

2 hours Free Cancellation

from
$1,490

Utuado Canyon River and Waterfall Private Tour in Puerto Rico

Experience our Utuado Canyon, River & Waterfall Private Tour in Puerto Rico! Embark on a serene journey through the picturesque landscapes of Puerto Rico as …More

Utuado, Puerto Rico

Utuado Canyon River and Waterfall Private Tour in Puerto Rico

Experience our Utuado Canyon, River & Waterfall Private Tour in Puerto Rico! Embark on a serene journey through the picturesque landscapes of Puerto Rico as...

8 hours Hotel pickup offered Free Cancellation

from
$292

Discover the pristine beauty of Culebra on a luxurious 6-hour boat tour aboard a 36 ft yacht. Experience a secure and comfortable navigation and discover …More

Culebra All Inclusive Luxury Private Yacht Tour

Discover the pristine beauty of Culebra on a luxurious 6-hour boat tour aboard a 36 ft yacht. Experience a secure and comfortable navigation and discover...

6 hours Free Cancellation

from
$2,700

Experience nature and the beauty of Jamaica with the Family Eco Adventure Tour, a true learning experience for both you and the family. Best of …More

Ocho Rios, Jamaica

Island Explorer 7 Days North Coast Tour

Experience nature and the beauty of Jamaica with the Family Eco Adventure Tour, a true learning experience for both you and the family. Best of...

7 days Hotel pickup offered Free Cancellation

from
$2,750

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?

Got any more Caribbean trip ideas?

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