Top Caribbean Private Sightseeing Tours

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 Yacht Tour w/optional Flying Dress Photoshoot Montego Bay

Luxurious Ultimate Private Caribbean Vacation Package!! 3-hour cruise includes: Various refreshments, including (Premium Alcohol and Rum Punch). Choice of KFC Chicken (includes fries, biscuits) or …More

Montego Bay, Jamaica

Private Yacht Tour w/optional Flying Dress Photoshoot Montego Bay

Luxurious Ultimate Private Caribbean Vacation Package!! 3-hour cruise includes: Various refreshments, including (Premium Alcohol and Rum Punch). Choice of KFC Chicken (includes fries, biscuits) or...

3 hours Hotel pickup offered Free Cancellation

from
$2,844

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! We …More

Private Half Day Afternoon Snorkel and Cruise on Serendipity

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! We...

4 hours Hotel pickup offered Free Cancellation

from
$2,897

Private Group Negril Catamarans Sailing and Snorkel Boat tours offer fun and excitement in Negril Jamaica . Sail and snorkel at excellent Sand reefs and …More

Negril, Jamaica

5.0 (1)

Private Catamaran Negril Jamaica Sail -Open Bar

Private Group Negril Catamarans Sailing and Snorkel Boat tours offer fun and excitement in Negril Jamaica . Sail and snorkel at excellent Sand reefs and...

3 hours Hotel pickup offered

5.0 (1)

from
$2,900

Private Full Day Luxury Catamaran Excursion

Enjoy a full-day sightseeing, relazing cruise on a 43ft Loepard Catamaran. See all of the top sights along the western coast of St Lucia. Enjoy …More

Cap Estate, St Lucia

5.0 (48)

Private Full Day Luxury Catamaran Excursion

Enjoy a full-day sightseeing, relazing cruise on a 43ft Loepard Catamaran. See all of the top sights along the western coast of St Lucia. Enjoy...

7 hours Hotel pickup offered Free Cancellation

5.0 (48)

from
$2,940

Day Yacht Excursions throughout the US or British Virgin Islands

Discover the heights of luxury at sea level with Magic Moments. This company is available on St Thomas and St John, has been voted BEST …More

4.9 (180)

Day Yacht Excursions throughout the US or British Virgin Islands

Discover the heights of luxury at sea level with Magic Moments. This company is available on St Thomas and St John, has been voted BEST...

6 to 8 hours Free Cancellation

4.9 (180)

from
$2,950

Private Afternoon Half Day Bottom Fishing Serendipity

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! Catch grouper, …More

5.0 (1)

Private Afternoon Half Day Bottom Fishing Serendipity

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! Catch grouper,...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$2,951

Robinson Crusoe Island Beach Hideaway Cruise Come aboard in Turks and Caicos for your amazing adventure on the crystal clear waters of TCI. We welcome …More

Robinson Crusoe Island Beach Hideaway Cruise

Robinson Crusoe Island Beach Hideaway Cruise Come aboard in Turks and Caicos for your amazing adventure on the crystal clear waters of TCI. We welcome...

4 hours Hotel pickup offered Free Cancellation

from
$2,963

Private Afternoon Tour Catamaran 44 Big Ben

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

4.9 (8)

Private Afternoon Tour Catamaran 44 Big Ben

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

4 hours Free Cancellation

4.9 (8)

from
$2,990

Noah's Ark Beach Club Tour Catamaran 44 Big Ben

Welcome aboard this catamaran for a unique experience in Turks and Caicos : Noah's Ark. Departing from Blue Haven Marina, we head straight to the …More

5.0 (1)

Noah's Ark Beach Club Tour Catamaran 44 Big Ben

Welcome aboard this catamaran for a unique experience in Turks and Caicos : Noah's Ark. Departing from Blue Haven Marina, we head straight to the...

4 hours Free Cancellation

5.0 (1)

from
$2,990

Full-day Private Tour in Turks and Caicos in a Luxury Axopar

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

5.0 (7)

Full-day Private Tour in Turks and Caicos in a Luxury Axopar

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...

8 hours Free Cancellation

5.0 (7)

from
$2,995

Looking to get out on the water and enjoy a dinner with friends and family while watching the sun set? Calypso is the perfect boat …More

5.0 (5)

Sunset Dinner Cruise Private Group

Looking to get out on the water and enjoy a dinner with friends and family while watching the sun set? Calypso is the perfect boat...

2 hours 30 minutes Free Cancellation

5.0 (5)

from
$3,000

We leave in the early hours of the morning of the hotels in Punta Cana and Bayahibe, buses with comfort and air conditioning, to reach …More

Catalina Island from the Roman special for cruises

We leave in the early hours of the morning of the hotels in Punta Cana and Bayahibe, buses with comfort and air conditioning, to reach...

4 hours Hotel pickup offered Free Cancellation

from
$3,000

Jamaica 8-Days Island Tour From Montego Bay

Exploring Jamaica on this 8-day sightseeing vacation tour package which will take you across Jamaica to experience some of the most amazing locations the island …More

Montego Bay, Jamaica

Jamaica 8-Days Island Tour From Montego Bay

Exploring Jamaica on this 8-day sightseeing vacation tour package which will take you across Jamaica to experience some of the most amazing locations the island...

8 days Hotel pickup offered Free Cancellation

from
$3,077

Private Charter Catamaran Sailing and Snorkeling

This catamaran sailing adventure is one of the most relaxing catamaran excursions found in Punta Cana. The catamaran passes along the Punta Cana coastline with …More

Punta Cana, Dominican Republic

Private Charter Catamaran Sailing and Snorkeling

This catamaran sailing adventure is one of the most relaxing catamaran excursions found in Punta Cana. The catamaran passes along the Punta Cana coastline with...

4 hours Hotel pickup offered

from
$3,125

Catamaran Cruise, Snorkeling and Dunn's River Falls

Basically this tour offers a 3 pack combo is like no other Enjoy an on-the-water adventure on a tour from Ocho Rios on board a …More

Ocho Rios, Jamaica

5.0 (1)

Catamaran Cruise, Snorkeling and Dunn's River Falls

Basically this tour offers a 3 pack combo is like no other Enjoy an on-the-water adventure on a tour from Ocho Rios on board a...

4 hours Free Cancellation

5.0 (1)

from
$3,200

Are you looking for the ultimate vacation experience? If you're in the mood for exploring the stunning reefs with some snorkeling and natural island beaches, …More

4 Hour Private 82' Luxury Mega Yacht Rental in Fajardo

Are you looking for the ultimate vacation experience? If you're in the mood for exploring the stunning reefs with some snorkeling and natural island beaches,...

4 hours Free Cancellation

from
$3,200

Private Tour: Barbados Catamaran Snorkeling Cruise

While you’re in paradise, treat yourself to a private catamaran cruise along Barbados’ west coast. Spread out and relax with your family and friends on …More

5.0 (18)

Private Tour: Barbados Catamaran Snorkeling Cruise

While you’re in paradise, treat yourself to a private catamaran cruise along Barbados’ west coast. Spread out and relax with your family and friends on...

5 hours

5.0 (18)

from
$3,210

Private Full Day Guided Snorkeling or Diving Charter in St Thomas

Avoid the crowds and get ready for fun, sun, and snorkeling on this unforgettable private trip! Perfect for friends and families who want to enjoy …More

5.0 (20)

Private Full Day Guided Snorkeling or Diving Charter in St Thomas

Avoid the crowds and get ready for fun, sun, and snorkeling on this unforgettable private trip! Perfect for friends and families who want to enjoy...

6 to 8 hours

5.0 (20)

from
$3,225

Spend the day out on the beautiful Caribbean Sea on this private sailing charter in St Maarten! Whether your group is 2 or 40, you …More

5.0 (58)

Private Sailboat Charter in St Maarten

Spend the day out on the beautiful Caribbean Sea on this private sailing charter in St Maarten! Whether your group is 2 or 40, you...

5 to 7 hours Free Cancellation

5.0 (58)

from
$3,300

3hr Private Luxury Yacht with Snorkeling, Bar, Food

3-Hour Cruise 1 Hors d'oeuvre (Assorted Sandwiches) Unlimited Rum Punch, Mimosas, Beer and Non-Alcoholic options Bluetooth Music Snorkeling with Gear Swimming with Toys Packaged Snack …More

5.0 (13)

3hr Private Luxury Yacht with Snorkeling, Bar, Food

3-Hour Cruise 1 Hors d'oeuvre (Assorted Sandwiches) Unlimited Rum Punch, Mimosas, Beer and Non-Alcoholic options Bluetooth Music Snorkeling with Gear Swimming with Toys Packaged Snack...

3 hours Free Cancellation

5.0 (13)

from
$3,300

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

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?