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 →

Aruba Half day Private Jeep Tour - Sightseeing and more

100% private experience - No strangers - No rushing - just you, your group and a local guide dedicated to making your trip unfrogettable - …More

5.0 (47)

Aruba Half day Private Jeep Tour - Sightseeing and more

100% private experience - No strangers - No rushing - just you, your group and a local guide dedicated to making your trip unfrogettable -...

4 hours Hotel pickup offered Free Cancellation

5.0 (47)

from
$595

Romana: Cave of wonders and Chavón from Santo Domingo.

We offer the best personalized service in Santo Domingo, our guides are trained to provide memorable experiences through good service, smiles and kindness; and our …More

Santo Domingo, Dominican Republic

4.9 (47)

Romana: Cave of wonders and Chavón from Santo Domingo.

We offer the best personalized service in Santo Domingo, our guides are trained to provide memorable experiences through good service, smiles and kindness; and our...

8 hours Hotel pickup offered Free Cancellation

4.9 (47)

from
$125

Private Island Hopping Boat Tour and view the Turtles

Enjoy an islanding hopping tour to nearby islands. You can choose to do snorkeling beautiful coral reefs, Gilligan's island, green cay and you can even …More

5.0 (46)

Private Island Hopping Boat Tour and view the Turtles

Enjoy an islanding hopping tour to nearby islands. You can choose to do snorkeling beautiful coral reefs, Gilligan's island, green cay and you can even...

4 hours Free Cancellation

5.0 (46)

from
$925

Private Full Day Charter to the British Virgin Islands from USVI

Explore the British Virgin Islands aboard a power catamaran built for comfortable full-day adventures around the islands. Whether you're looking for world-class snorkeling, legendary beach …More

5.0 (46)

Private Full Day Charter to the British Virgin Islands from USVI

Explore the British Virgin Islands aboard a power catamaran built for comfortable full-day adventures around the islands. Whether you're looking for world-class snorkeling, legendary beach...

8 hours Free Cancellation

5.0 (46)

from
$1,695

Puerto Rico Private Catamaran Sail from Fajardo

Embark on a carefree Caribbean sailing vacation to enjoy the beautiful views of the east coastline and nearby cays of Puerto Rico. Our 5 star …More

Fajardo, Puerto Rico

5.0 (46)

Puerto Rico Private Catamaran Sail from Fajardo

Embark on a carefree Caribbean sailing vacation to enjoy the beautiful views of the east coastline and nearby cays of Puerto Rico. Our 5 star...

6 hours Free Cancellation

5.0 (46)

from
$2,000

Costumizable Private Curaçao Jewish Heritage Tour Experience

This private Jewish Heritage Tour is for up to 4 passengers. You will visit places that are known and some places that are not so …More

Willemstad, Curacao

5.0 (46)

Costumizable Private Curaçao Jewish Heritage Tour Experience

This private Jewish Heritage Tour is for up to 4 passengers. You will visit places that are known and some places that are not so...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (46)

from
$600

Punta Cana Half-Day Private Party Boat with Drinks and Snorkeling

Make the most of Punta Cana’s seas on a private snorkel catamaran tour. Prebook to secure your ideal cruise time and join family or friends …More

Punta Cana, Dominican Republic

4.9 (46)

Punta Cana Half-Day Private Party Boat with Drinks and Snorkeling

Make the most of Punta Cana’s seas on a private snorkel catamaran tour. Prebook to secure your ideal cruise time and join family or friends...

4 hours 10 minutes Hotel pickup offered Free Cancellation

4.9 (46)

from
$900

ATV Riding, Bamboo Rafting and Ricks Café from Montego Bay

Guaranteed the best Experience ever!! Double the Fun with the SAFARI ATV-RIDING and RICKS CAFÉ combo.. get transported in a private vehicle to the Attractions, …More

Montego Bay, Jamaica

5.0 (46)

ATV Riding, Bamboo Rafting and Ricks Café from Montego Bay

Guaranteed the best Experience ever!! Double the Fun with the SAFARI ATV-RIDING and RICKS CAFÉ combo.. get transported in a private vehicle to the Attractions,...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (46)

from
$20

Private 1/2 Day Yacht Charter in Bonaire - Customizable!

100% Customizable! Our private charter experience on Bonaire is unmatched. As the only American yacht operators on the island, we understand the importance of personalized …More

5.0 (46)

Private 1/2 Day Yacht Charter in Bonaire - Customizable!

100% Customizable! Our private charter experience on Bonaire is unmatched. As the only American yacht operators on the island, we understand the importance of personalized...

4 hours 30 minutes

5.0 (46)

from
$2,299

This private charter lets you have the boat to yourselves along with Bermuda's best captain while you cruise into a Bermudaful sunset, relaxing and sipping …More

4.9 (46)

Private Sunset Cruise & Rum Swizzle

This private charter lets you have the boat to yourselves along with Bermuda's best captain while you cruise into a Bermudaful sunset, relaxing and sipping...

1 hour Free Cancellation

4.9 (46)

from
$500

Blue Hole Secret Falls Excursions Best Water Falls in Jamaica

Blue Hole or Secret Falls in Ocho Rios Jamaica is a perfect alternative if you have been to Dunns River Falls before and would like …More

Falmouth, Jamaica

4.9 (46)

Blue Hole Secret Falls Excursions Best Water Falls in Jamaica

Blue Hole or Secret Falls in Ocho Rios Jamaica is a perfect alternative if you have been to Dunns River Falls before and would like...

5 to 7 hours Hotel pickup offered Free Cancellation

4.9 (46)

from
$75

2 hour private boat tour - Spanish Waters, Swim Stop & Boarding

Join us on board! We are a small family business. Personalized service is very important to us; therefore our trips are operated in small groups. …More

5.0 (45)

2 hour private boat tour - Spanish Waters, Swim Stop & Boarding

Join us on board! We are a small family business. Personalized service is very important to us; therefore our trips are operated in small groups....

2 hours Free Cancellation

5.0 (45)

from
$375

Private Bamboo Rafting and Horseback Riding from Ocho Rios

Come experience this adventurous and relaxing adventure that is sure to turn up the thrill in every thrill seeker. No matter what your family fun …More

Kingston, Jamaica

4.9 (45)

Private Bamboo Rafting and Horseback Riding from Ocho Rios

Come experience this adventurous and relaxing adventure that is sure to turn up the thrill in every thrill seeker. No matter what your family fun...

3 to 4 hours Hotel pickup offered Free Cancellation

4.9 (45)

from
$115

Lagoon Cave and Secluded Beaches Tour in Puerto Rico

This intermediate semi-adventure explores Puerto Rico's north coast. Visit Playa La Cueva Las Golondrinas in Manatí, swim at Charco Azul in Vega Baja, and finish …More

4.8 (45)

Lagoon Cave and Secluded Beaches Tour in Puerto Rico

This intermediate semi-adventure explores Puerto Rico's north coast. Visit Playa La Cueva Las Golondrinas in Manatí, swim at Charco Azul in Vega Baja, and finish...

6 to 7 hours Hotel pickup offered Free Cancellation

4.8 (45)

from
$145

Private 4x4 Natural Pool, Caves & Baby Beach by Cross Aruba Tours

Private tour for your family and friends. Tour around the island in our very comfortable open air jeep with licensed tour guide driver. See the …More

Oranjestad, Aruba

5.0 (44)

Private 4x4 Natural Pool, Caves & Baby Beach by Cross Aruba Tours

Private tour for your family and friends. Tour around the island in our very comfortable open air jeep with licensed tour guide driver. See the...

4 hours Hotel pickup offered Free Cancellation

5.0 (44)

from
$600

Jamaica Best Water Falls Tour,Mobay Bay to Dunn's River/Blue Hole

This is a Hassle Free Tour, which INCLUDES ENTRANCE FEES AND TRANSPORTATION COSTS. We picks you up at your hotel or cruise ship port. A …More

Kingston, Jamaica

5.0 (44)

Jamaica Best Water Falls Tour,Mobay Bay to Dunn's River/Blue Hole

This is a Hassle Free Tour, which INCLUDES ENTRANCE FEES AND TRANSPORTATION COSTS. We picks you up at your hotel or cruise ship port. A...

7 to 9 hours Hotel pickup offered Free Cancellation

5.0 (44)

from
$192

3 Hours Private Boat Includes Snorkeling & Swim with turtles

Experience Aruba’s stunning coastline aboard a private speed boat charter. This exclusive 3 hour adventure is perfect for families, friends, and small groups looking for …More

5.0 (43)

3 Hours Private Boat Includes Snorkeling & Swim with turtles

Experience Aruba’s stunning coastline aboard a private speed boat charter. This exclusive 3 hour adventure is perfect for families, friends, and small groups looking for...

3 hours Free Cancellation

5.0 (43)

from
$900

Aruba Island Private Jeep Tour Arikok Park & Baby beach

Transfers from the port or hotels are included Ideal for first time travelers who are short time in Aruba Refreshments and one Local snack included …More

5.0 (43)

Aruba Island Private Jeep Tour Arikok Park & Baby beach

Transfers from the port or hotels are included Ideal for first time travelers who are short time in Aruba Refreshments and one Local snack included...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (43)

from
$800

Local Legend Charters: Explore St. John! (Full or Half Day)

3rd generation Family/locally owned/operated business providing Private, customizable Boat Charters, Day trips and tours of the Virgin Islands, including sightseeing, boating, swimming, snorkeling, beach and …More

Cruz Bay, US Virgin Islands

5.0 (43)

Local Legend Charters: Explore St. John! (Full or Half Day)

1 to 11 hours Hotel pickup offered Free Cancellation

5.0 (43)

from
$950

Dunn's River Falls & Blue Hole tour from Montego bay & Falmouth.

Explore two of Jamaica's most visited natural treasure.Book with us for a safe enjoyable moment where you will be picked up from your desired location …More

Runaway Bay, Jamaica

5.0 (43)

Dunn's River Falls & Blue Hole tour from Montego bay & Falmouth.

Explore two of Jamaica's most visited natural treasure.Book with us for a safe enjoyable moment where you will be picked up from your desired location...

7 hours Hotel pickup offered Free Cancellation

5.0 (43)

from
$142

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?