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: Private Horseback Riding And Ricks Cafe Tour. Airport Transportation Private Vacation Photoshoot in Montego Bay,Jamaica Blue Hole and Horseback Riding from Montego bay ATV Adventures with Private Transportation

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 →

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Saint-Martin as you make your way to …More

Private Tour French And Dutch Sightseeing And Grand Case Beach

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Saint-Martin as you make your way to...

7 hours Hotel pickup offered

from
$443

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Saint-Martin as you make your way to …More

Private Tour Sunset in Saint Maarten

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Saint-Martin as you make your way to...

5 hours Hotel pickup offered

from
$443

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Saint-Martin as you make your way to …More

Private Tour Snorkeling in Saint-Martin

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Saint-Martin as you make your way to...

6 hours Hotel pickup offered

from
$443

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Trinidad and Tobago as you make your …More

Private Tour Full Island Tobago

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of Trinidad and Tobago as you make your...

9 hours Hotel pickup offered

from
$444

4-Hour Exploring St. Thomas Private and Guided Jeep Tour

Imagine spending four hours exploring the beautiful sites of St. Thomas with your own local private tour guide at your own pace and visiting the …More

4.9 (11)

4-Hour Exploring St. Thomas Private and Guided Jeep Tour

Imagine spending four hours exploring the beautiful sites of St. Thomas with your own local private tour guide at your own pace and visiting the...

4 hours Hotel pickup offered Free Cancellation

4.9 (11)

from
$445

V.I.P North Caribbean deep forest Tour -The Green Martinique

We thrive to make you discover a maximum about our island within the timing you have.On this tour you will enjoy nature and all the …More

5.0 (1)

V.I.P North Caribbean deep forest Tour -The Green Martinique

We thrive to make you discover a maximum about our island within the timing you have.On this tour you will enjoy nature and all the...

2 to 4 hours

5.0 (1)

from
$446

Private Tour for Two: Romantic Curacao by Land and Sea

Experience Curacao in the most romantic way possible. This private tour covers both land and sea, and includes equipment, snacks, beverages, and pickup/drop-off at your …More

5.0 (2)

Private Tour for Two: Romantic Curacao by Land and Sea

Experience Curacao in the most romantic way possible. This private tour covers both land and sea, and includes equipment, snacks, beverages, and pickup/drop-off at your...

8 hours

5.0 (2)

from
$447

Private Historical Scenic Tour in Santo Domingo Colonial

This private historical tour explores Santo Domingo Old Town, a UNESCO Heritage site shaped by ancient civilization. You walk through Colonial Zone streets where cultural …More

Santo Domingo, Dominican Republic

5.0 (4)

Private Historical Scenic Tour in Santo Domingo Colonial

This private historical tour explores Santo Domingo Old Town, a UNESCO Heritage site shaped by ancient civilization. You walk through Colonial Zone streets where cultural...

8 hours Hotel pickup offered

5.0 (4)

from
$449

Half Day Cultural Jeep Beach Adventure - 4 Hr Tour St. Thomas

Up to 16 guests can join a native local guide, as they share their island home with you. You'll see all the main attractions, visit …More

5.0 (226)

Half Day Cultural Jeep Beach Adventure - 4 Hr Tour St. Thomas

Up to 16 guests can join a native local guide, as they share their island home with you. You'll see all the main attractions, visit...

4 hours Hotel pickup offered Free Cancellation

5.0 (226)

from
$450

This experience blends three of Aguadilla’s most iconic landmarks into one smooth, time-friendly adventure you won’t find anywhere else. Unlike standard beach excursions, this tour …More

Rincón, Puerto Rico

5.0 (18)

Puerto Rico: Crash Boat UTV Experience

This experience blends three of Aguadilla’s most iconic landmarks into one smooth, time-friendly adventure you won’t find anywhere else. Unlike standard beach excursions, this tour...

2 hours 30 minutes Free Cancellation

5.0 (18)

from
$450

Make yourself comfortable in our Private luxurious, fully air-conditioned Jeep Wrangler and get a tour of Antigua. You have the option of air-conditioning or semi-roof …More

Five Islands Village, Antigua and Barbuda

4.7 (31)

SoCoHo Luxe Private Jeep Wrangler Tour

Make yourself comfortable in our Private luxurious, fully air-conditioned Jeep Wrangler and get a tour of Antigua. You have the option of air-conditioning or semi-roof...

5 to 6 hours Hotel pickup offered Free Cancellation

4.7 (31)

from
$450

Private Tour of Puerto Plata by Classic Car

Discover the unique and nostalgic charm of a classic car tour around Puerto Plata. Immerse yourself in a bygone era as you ride in a …More

4.3 (52)

Private Tour of Puerto Plata by Classic Car

Discover the unique and nostalgic charm of a classic car tour around Puerto Plata. Immerse yourself in a bygone era as you ride in a...

1 to 120 minutes Hotel pickup offered Free Cancellation

4.3 (52)

from
$450

Deep Sea Fishing (Street Food and Beer Included)

The tour is suitable both for beginners and more experienced fishers! We will teach you everything you need to know about deep sea fishing in …More

5.0 (6)

Deep Sea Fishing (Street Food and Beer Included)

The tour is suitable both for beginners and more experienced fishers! We will teach you everything you need to know about deep sea fishing in...

4 hours Hotel pickup offered

5.0 (6)

from
$450

Feel like a million bucks and book your Jamaica Flying Dress Photoshoot with Kevin Wright. Perfect gift for anniversary, birthday, girls trip. Please bring your …More

Montego Bay, Jamaica

4.3 (11)

Jamaica Flying Dress Photoshoots

Feel like a million bucks and book your Jamaica Flying Dress Photoshoot with Kevin Wright. Perfect gift for anniversary, birthday, girls trip. Please bring your...

1 to 2 hours

4.3 (11)

from
$450

St Maarten French And Dutch Sightseeing And Grand Case Beach Tour

From the Philipsburg cruise port Meet your friendly guide. And board a comfortable, air-conditioned van for transport to take you to three amazing stop on …More

5.0 (1)

St Maarten French And Dutch Sightseeing And Grand Case Beach Tour

From the Philipsburg cruise port Meet your friendly guide. And board a comfortable, air-conditioned van for transport to take you to three amazing stop on...

4 hours Free Cancellation

5.0 (1)

from
$450

Private Local lunch and Kralendijk neighborhood tour

Experience the Bario's of Bonaire with an accurate narrative on the lifestyle of the local Bonairian's. Travel through 2 neighborhoods where your guide will describe …More

Kralendijk, Bonaire

5.0 (1)

Private Local lunch and Kralendijk neighborhood tour

Experience the Bario's of Bonaire with an accurate narrative on the lifestyle of the local Bonairian's. Travel through 2 neighborhoods where your guide will describe...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$450

Private Blue Hole & Secret Falls Day Trip plus Shopping from Montego Bay Hotels

This private tour is unique and tailored just for you and your party. You have your own private driver/guide for a more personalized service and …More

Montego Bay, Jamaica

4.3 (3)

Private Blue Hole & Secret Falls Day Trip plus Shopping from Montego Bay Hotels

This private tour is unique and tailored just for you and your party. You have your own private driver/guide for a more personalized service and...

8 hours Hotel pickup offered Free Cancellation

4.3 (3)

from
$450

No others will join your group. You can plan your own itenerary what you'd like. Others don't have to wait for you and you don't …More

4.0 (3)

Private Tour of Bonaire

No others will join your group. You can plan your own itenerary what you'd like. Others don't have to wait for you and you don't...

3 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$450

This tour was designed by a group of travelers who loved the idea of visiting many of the botanical gardens available in Barbados. Ever since …More

Bridgetown, Barbados

5.0 (1)

Barbados Botanical Tour

This tour was designed by a group of travelers who loved the idea of visiting many of the botanical gardens available in Barbados. Ever since...

7 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$450

ATV Adventure & Catamaran Cruise -From MoBay, Negril, Ocho Rios

Our ATV Adventure & Catamaran Cruise offers the perfect blend of Jamaican adventure and Caribbean relaxation in one exciting experience. Instead of spending your day …More

Lucea, Jamaica

3.0 (1)

ATV Adventure & Catamaran Cruise -From MoBay, Negril, Ocho Rios

Our ATV Adventure & Catamaran Cruise offers the perfect blend of Jamaican adventure and Caribbean relaxation in one exciting experience. Instead of spending your day...

5 to 15 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$450

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?