Top Caribbean City Tours

Q: What are the best options for Caribbean City Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Caribbean City Tours are: Botanical Gardens and City Tour Private Custom Tour of Martinique Montego Bay Highlights, Margaritaville & Shopping Tour Santo Domingo: City Highlights Guided Bike Tour St. Kitts Full Island Excursion

Q: What are the best kid-friendly options for Caribbean City Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean City Tours are: Punta Cana Shopping Tour Montego Bay Private Shopping Tour with Hotel Pickup Ocho Rios Shopping Tour Historic Walking Tour of Bridgetown Barbados Grand Turk Historical Sightseeing Tour View all kid-friendly Tours →

Q: Which Caribbean City Tours have Instant Confirmation?

Caribbean City Tours with Instant Confirmation include: San Juan Self-Guided Walking Audio Tour Punta Cana Shopping Tour Montego Bay Private Shopping Tour with Hotel Pickup Private Tour Souvenir Shopping in Montego Bay Ocho Rios Shopping Tour View all Tours with Instant Confirmation →

Q: Which Caribbean City Tours have Free Cancellation?

Caribbean City Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include: San Juan Self-Guided Walking Audio Tour Punta Cana Shopping Tour Montego Bay Private Shopping Tour with Hotel Pickup Rick's Cafe & Shopping in Negril Private Tour Souvenir Shopping in Montego Bay View all Tours with Free Cancellation →

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

No problem. These Caribbean City Tours include Hotel Pickup: Punta Cana Shopping Tour Montego Bay Private Shopping Tour with Hotel Pickup Private Tour Souvenir Shopping in Montego Bay Ocho Rios Shopping Tour Montego Bay City Highlights & Sightseeing Tour with Shopping 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 →

This will be one of the best tours you did in your life. 4 amazing stops in 4 hours, you will get time to hang …More

Philipsburg, St Maarten

4.7 (41)

St. Maarten 4 Hour Sightseeing Tour

This will be one of the best tours you did in your life. 4 amazing stops in 4 hours, you will get time to hang...

4 hours Hotel pickup offered Free Cancellation

4.7 (41)

from
$62

Puerto Plata Private City Tour with Local Guide

This is a private Tour where we transport you safely on an air conditioned car. Your Guide will show you the high spots of Puerto …More

Puerto Plata, Dominican Republic

4.8 (61)

Puerto Plata Private City Tour with Local Guide

This is a private Tour where we transport you safely on an air conditioned car. Your Guide will show you the high spots of Puerto...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (61)

from
$62

Montego Bay Highlights, Margaritaville & Shopping Tour

Experience the fascinating history and vibrant culture of Montego Bay with Fun, Sun and Sand Tours! Our private historical and culture tour offers a customizable …More

Lucea, Jamaica

4.8 (27)

Montego Bay Highlights, Margaritaville & Shopping Tour

Experience the fascinating history and vibrant culture of Montego Bay with Fun, Sun and Sand Tours! Our private historical and culture tour offers a customizable...

4 hours Hotel pickup offered Free Cancellation

4.8 (27)

from
$62

Saona Island is paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees. We will pick you up in …More

Punta Cana, Dominican Republic

4.0 (300)

Full-Day Excursion in Saona Island

Saona Island is paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees. We will pick you up in...

10 hours Hotel pickup offered Free Cancellation

4.0 (300)

from
$64

Private Tour of Negril Beach and Sunset at Ricks Cafe

This tour includes scenic drive along the West Coastline of the island, Jamaica’s number 1 Beach destination, Negril. Negril is known for its seven-mile stretch …More

Montego Bay, Jamaica

5.0 (11)

Private Tour of Negril Beach and Sunset at Ricks Cafe

This tour includes scenic drive along the West Coastline of the island, Jamaica’s number 1 Beach destination, Negril. Negril is known for its seven-mile stretch...

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$64

Private Montego Bay Customized Tour with pickup & Bamboo Rafting

After collecting you, our first stop will be the picturesque Lethe Estate where you can enjoy rafting and a limestone foot massage while drifting through …More

Montego Bay, Jamaica

5.0 (9)

Private Montego Bay Customized Tour with pickup & Bamboo Rafting

After collecting you, our first stop will be the picturesque Lethe Estate where you can enjoy rafting and a limestone foot massage while drifting through...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (9)

from
$64

Private Tour in Puerto Plata and La Playa

On this tour we will be visiting the street of the umbrella, the fortress, the pink alley, we will also have a panoramic view of …More

Puerto Plata, Dominican Republic

4.8 (216)

Private Tour in Puerto Plata and La Playa

On this tour we will be visiting the street of the umbrella, the fortress, the pink alley, we will also have a panoramic view of...

3 to 4 hours Hotel pickup offered Free Cancellation

4.8 (216)

from
$65

Discover history, culture, and flavors of Puerto Plata on a city tour lasting approx 3 hours. Begin at Rum factory, where you’ll learn about Dominican …More

Cabarete, Dominican Republic

4.9 (167)

Puerto Plata City Private Tour

Discover history, culture, and flavors of Puerto Plata on a city tour lasting approx 3 hours. Begin at Rum factory, where you’ll learn about Dominican...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (167)

from
$65

Private Montego Bay Customized Tour with Pickup and Guide

Booking with me means you'll get an authentic Jamaican experience tailored to showcase the best of what my country has to offer. As a local, …More

Trelawny, Jamaica

4.9 (153)

Private Montego Bay Customized Tour with Pickup and Guide

Booking with me means you'll get an authentic Jamaican experience tailored to showcase the best of what my country has to offer. As a local,...

3 hours Hotel pickup offered Free Cancellation

4.9 (153)

from
$65

To get to know the real Jamaica, you need to walk its lively streets. On this 5-hour walking tour of Kingston, you will explore the …More

Kingston, Jamaica

4.7 (13)

Cultural Walking Tour of Kingston

To get to know the real Jamaica, you need to walk its lively streets. On this 5-hour walking tour of Kingston, you will explore the...

4 to 5 hours

4.7 (13)

from
$65

San Juan Urban Art Bike Tour 2 Hour and 4 Hour Options

Discover the vibrant street art of San Juan on a guided bike tour through Santurce or Río Piedras. Experience the city's rich culture and history …More

5.0 (13)

San Juan Urban Art Bike Tour 2 Hour and 4 Hour Options

Discover the vibrant street art of San Juan on a guided bike tour through Santurce or Río Piedras. Experience the city's rich culture and history...

1 to 2 hours Free Cancellation

5.0 (13)

from
$65

Private Countryside and City Tour in Puerto Plata

This tour will take you to discover the rich culture, delicious cuisine and stunning landscapes of this beautiful city. We focus on learning more about …More

Puerto Plata, Dominican Republic

4.8 (8)

Private Countryside and City Tour in Puerto Plata

This tour will take you to discover the rich culture, delicious cuisine and stunning landscapes of this beautiful city. We focus on learning more about...

3 to 4 hours Hotel pickup offered Free Cancellation

4.8 (8)

from
$65

Puerto Plata City Tour, History & Culture Tour, Cruise Speci

Travel between highlights of Puerto Plata with ease Hassle-free round-trip transport included on this Puerto Plata Tour Rum Factory, look the local architecture, and take …More

Puerto Plata, Dominican Republic

4.3 (19)

Puerto Plata City Tour, History & Culture Tour, Cruise Speci

Travel between highlights of Puerto Plata with ease Hassle-free round-trip transport included on this Puerto Plata Tour Rum Factory, look the local architecture, and take...

5 hours 30 minutes Hotel pickup offered Free Cancellation

4.3 (19)

from
$65

Falmouth Shore Excursion: Private Montego Bay City Tour

Take a private, guided-tour through the city of Montego Bay. You will visit historical sites and learn about the history of Jamaica. This is the …More

Trelawny, Jamaica

5.0 (2)

Falmouth Shore Excursion: Private Montego Bay City Tour

Take a private, guided-tour through the city of Montego Bay. You will visit historical sites and learn about the history of Jamaica. This is the...

4 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$65

CITY TOUR PUERTO PLATA: Explore the City

You will be able to see the most iconic places in Puerto Plata, we have highly qualified staff who will be willing to make your …More

Puerto Plata, Dominican Republic

5.0 (1)

CITY TOUR PUERTO PLATA: Explore the City

You will be able to see the most iconic places in Puerto Plata, we have highly qualified staff who will be willing to make your...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$65

What sets us apart is the fact that we make sure we do our best to not make the tour drawn out and boring. But …More

5.0 (2)

Reggae and Rum Sightseeing Tours

What sets us apart is the fact that we make sure we do our best to not make the tour drawn out and boring. But...

2 hours Free Cancellation

5.0 (2)

from
$65

We will show you our beautiful and picturesque island. It will be a pleasant and comfortable ride with air conditioning and very friendly guides. …More

Willemstad, Curacao

4.7 (3)

Curaçao Highlights & Beach

We will show you our beautiful and picturesque island. It will be a pleasant and comfortable ride with air conditioning and very friendly guides....

4 hours Hotel pickup offered Free Cancellation

4.7 (3)

from
$65

The Ghosts of San Juan: Private 2.5-hour Spooky Evening Tour

Your tour begins in Columbus Square, where your expert private guide will introduce you to the city’s tenuous relationship with the notorious explorer. In June …More

4.0 (1)

The Ghosts of San Juan: Private 2.5-hour Spooky Evening Tour

Your tour begins in Columbus Square, where your expert private guide will introduce you to the city’s tenuous relationship with the notorious explorer. In June...

2 hours 30 minutes Free Cancellation

4.0 (1)

from
$65

Montego Bay Shopping Tours takes you on a journey through one of the world's most famous tourist destinations Montego Bay. Visit the historical sites, residential …More

Montego Bay, Jamaica

5.0 (1)

Montego Bay Shopping Tours 3 Hours

Montego Bay Shopping Tours takes you on a journey through one of the world's most famous tourist destinations Montego Bay. Visit the historical sites, residential...

2 to 3 minutes Hotel pickup offered

5.0 (1)

from
$65