Top Caribbean Private Sightseeing Tours

Q: 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: Spice Island Taxi Tour Bamboo Rafting and Catamaran Cruise Party Boat Tour Montego Bay Private Trip to Los Haitises from Sabana De La Mar St. Maarten/Saint Martin Island Tour Night Life, Party Vibes & Clubbing in Montego Bay

Q: 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: San Juan’s Historic Streets Audio Guided Walking Tour Montego Bay Private Hotel & Airport Transfer – MBJ Historical attractions of Alexander Hamillton Mother's Gravesite Ricks Cafe Negril and 7 Mile Beach Day Trip Montego Bay Shopping View all kid-friendly Tours →

Q: I need a ride! Which Caribbean Private Sightseeing Tours have Hotel Pickup?

No problem. These Caribbean Private Sightseeing Tours include Hotel Pickup: Private Airport Transfers Roundtrip Punta Cana Hotels Souvenir Shopping Tour in Punta Cana. Transportation Included Great River Raft and Full Limestone body Massage In Montego Bay Ricks Cafe Negril and 7 Mile Beach Day Trip Punta Cana Shopping tour 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 →

Private Stingray City Snorkeling and BioBay Charter for 6 Guests

This private 6 hour afternoon & evening adventure is a wonderful combination of daytime fun, sunset dining and Bio Bay magic. Your 2-person crew with …More

Grand Cayman, Cayman Islands

5.0 (37)

Private Stingray City Snorkeling and BioBay Charter for 6 Guests

This private 6 hour afternoon & evening adventure is a wonderful combination of daytime fun, sunset dining and Bio Bay magic. Your 2-person crew with...

6 hours

5.0 (37)

from
$1,600

mini Burger or Taco menu Private Luxury Party Boat

Charter a deluxe party boat for your own personal cruise around Punta Cana. Step on board to meet a staff whose job is to cater …More

Punta Cana, Dominican Republic

4.0 (2)

mini Burger or Taco menu Private Luxury Party Boat

Charter a deluxe party boat for your own personal cruise around Punta Cana. Step on board to meet a staff whose job is to cater...

4 hours Hotel pickup offered Free Cancellation

4.0 (2)

from
$1,600

Indulge in the ultimate luxury with a private charter to St. Barts. Experience unparalleled comfort aboard high-end vessel, customized to your desires. Whether you're cruising …More

Saint Barth Prestige Private Charter

Indulge in the ultimate luxury with a private charter to St. Barts. Experience unparalleled comfort aboard high-end vessel, customized to your desires. Whether you're cruising...

6 to 8 hours Free Cancellation

from
$1,600

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

Private Full Day Sail in Virgin Islands National Park

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some …More

5.0 (16)

Private Full Day Sail in Virgin Islands National Park

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some...

6 hours Free Cancellation

5.0 (16)

from
$1,650

Private Full Day Baths and Beyond Tour in Tortola BVI

Antilles Power Boats will take you on a breathtaking adventure to see all the best of the BVI and give you a day to remember. …More

Tortola, British Virgin Islands

5.0 (21)

Private Full Day Baths and Beyond Tour in Tortola BVI

Antilles Power Boats will take you on a breathtaking adventure to see all the best of the BVI and give you a day to remember....

7 hours Free Cancellation

5.0 (21)

from
$1,650

Private Catamaran Sunset Cruise in Turks and Caicos

Join us on this fully customizable private catamaran sunset cruise in the beautiful Grace Bay in Turks and Caicos. This memorable excursion will depart from …More

4.8 (4)

Private Catamaran Sunset Cruise in Turks and Caicos

Join us on this fully customizable private catamaran sunset cruise in the beautiful Grace Bay in Turks and Caicos. This memorable excursion will depart from...

2 hours Free Cancellation

4.8 (4)

from
$1,650

Enjoy a day in Paradise!! in a private boat, away from the crowd. On our Full Day Tour you will be able to enjoy up …More

5.0 (15)

Full Day Private Boat Tour To Culebra

Enjoy a day in Paradise!! in a private boat, away from the crowd. On our Full Day Tour you will be able to enjoy up...

7 hours Free Cancellation

5.0 (15)

from
$1,650

Half-Day Private Catamaran Tour in Puerto Plata

Have a blast on the water! Take a 38 feet catamaran, ride along the coast and have a party of your life, while dancing, sipping …More

Cabarete, Dominican Republic

5.0 (1)

Half-Day Private Catamaran Tour in Puerto Plata

Have a blast on the water! Take a 38 feet catamaran, ride along the coast and have a party of your life, while dancing, sipping...

5 hours Hotel pickup offered

5.0 (1)

from
$1,650

Amber Cove & Taino Bay Shore Excursion, Private Charter on Blue Sky Catamaran

Have a blast on the water! Take a Blue Sky Party Boat ride along the North Coast and have a party of your life, while …More

Puerto Plata, Dominican Republic

5.0 (8)

Amber Cove & Taino Bay Shore Excursion, Private Charter on Blue Sky Catamaran

Have a blast on the water! Take a Blue Sky Party Boat ride along the North Coast and have a party of your life, while...

4 to 5 hours

5.0 (8)

from
$1,663

Immerse yourself in the unforgettable allure of Anguilla on your private boat, a day that will linger in your memory. Let Pierre be your expert …More

4.8 (16)

Full Day Anguilla Private Charter Tour

Immerse yourself in the unforgettable allure of Anguilla on your private boat, a day that will linger in your memory. Let Pierre be your expert...

8 hours Free Cancellation

4.8 (16)

from
$1,665

Private Boat Swim and Snorkel Adventure to Rose Island

Welcome to Paradise, where luxury meets nature in a harmonious blend of serenity and adventure. This private island retreat offers a unique experience like no …More

5.0 (26)

Private Boat Swim and Snorkel Adventure to Rose Island

Welcome to Paradise, where luxury meets nature in a harmonious blend of serenity and adventure. This private island retreat offers a unique experience like no...

4 hours Free Cancellation

5.0 (26)

from
$1,670

4HR-Halfday Private Fishing Tour in Gracebay

Indulge your love for fishing with this exciting family excursion in the beautiful waters of the Turks and Caicos. Reel in the common catches of …More

5.0 (68)

4HR-Halfday Private Fishing Tour in Gracebay

Indulge your love for fishing with this exciting family excursion in the beautiful waters of the Turks and Caicos. Reel in the common catches of...

4 hours Hotel pickup offered Free Cancellation

5.0 (68)

from
$1,680

Private Half-Day Luxury Catamaran Experience

Enjoy a half-day cruise on our luxurious 43ft Leopard Catamaran. See all of the top sights along the western coast of St Lucia. Onboard we …More

Cap Estate, St Lucia

4.9 (22)

Private Half-Day Luxury Catamaran Experience

Enjoy a half-day cruise on our luxurious 43ft Leopard Catamaran. See all of the top sights along the western coast of St Lucia. Onboard we...

4 hours Free Cancellation

4.9 (22)

from
$1,680

Private Luxury 36' Yacht from Fajardo to Icacos or Palomino

Private Boat Tour -All-Inclusive - Top Service Navigate without crowds, long queues, and strict schedules. Visit one of the Fajardo Keys— Palomino, Icacos, or Piñero …More

Fajardo, Puerto Rico

5.0 (29)

Private Luxury 36' Yacht from Fajardo to Icacos or Palomino

Private Boat Tour -All-Inclusive - Top Service Navigate without crowds, long queues, and strict schedules. Visit one of the Fajardo Keys— Palomino, Icacos, or Piñero...

6 hours Free Cancellation

5.0 (29)

from
$1,690

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

Half Day Private Luxury Axopar Charter in Turks & Caicos

Hop aboard and relax on the sundeck of one of our stylish Axopar 37′ while your captain navigates you through the emerald waters of Grace …More

4.9 (26)

Half Day Private Luxury Axopar Charter in Turks & Caicos

Hop aboard and relax on the sundeck of one of our stylish Axopar 37′ while your captain navigates you through the emerald waters of Grace...

4 hours Free Cancellation

4.9 (26)

from
$1,695

Private Charter 37' Axopar in US Virgin Islands

Stormy Pirates Boat Charters is a family owned and operated company serving both St.Thomas and St. John. This private trip is completely customizable for your …More

5.0 (85)

Private Charter 37' Axopar in US Virgin Islands

Stormy Pirates Boat Charters is a family owned and operated company serving both St.Thomas and St. John. This private trip is completely customizable for your...

6 hours

5.0 (85)

from
$1,695

Full Day Private Boat Charter to the British Virgin Island

Embark on a BVI adventure with Carpe Diem Charters, your powerboat passport to paradise. Cruise turquoise waters, uncover hidden coves, and relish unforgettable moments. With …More

5.0 (58)

Full Day Private Boat Charter to the British Virgin Island

Embark on a BVI adventure with Carpe Diem Charters, your powerboat passport to paradise. Cruise turquoise waters, uncover hidden coves, and relish unforgettable moments. With...

8 hours Free Cancellation

5.0 (58)

from
$1,700

Float & Feast Private Party Cruise with Premium Buffet & Open Bar

Our tour is not just a boat ride — it’s your own private party at sea! What sets us apart is the perfect mix of …More

Punta Cana, Dominican Republic

5.0 (18)

Float & Feast Private Party Cruise with Premium Buffet & Open Bar

Our tour is not just a boat ride — it’s your own private party at sea! What sets us apart is the perfect mix of...

4 hours Hotel pickup offered Free Cancellation

5.0 (18)

from
$1,700

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?

Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Caribbean Private Sightseeing Tours with Instant Confirmation include:

View all Tours with 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?