Top Caribbean Wine Tasting & Winery Tours

Q: What are the best options for Caribbean Wine Tasting & Winery Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Caribbean Wine Tasting & Winery Tours are: City Sight Seeing with Wine, Rum Cake and Conch Fritter Samples Luxury Private Sunset Cruise for up to 6 guests Cheese and Wine Tasting St.Lucia Rum & Mud Bath Tour Wine Maker Class at Bahama Barrels

Q: What are the best kid-friendly options for Caribbean Wine Tasting & Winery Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean Wine Tasting & Winery Tours are: Private transportation to Montego Bay clubs and Street Food Nassau Guided City Tour Graycliff And Queen's Staircase Exclusive Sunset Dinner At Reggae Hill Sunset Dinner at Bamboo Beach Club Rhythm Of Rum Tour & Rum Tasting Saint Lucia View all kid-friendly Tours →

Q: Which Caribbean Wine Tasting & Winery Tours have Instant Confirmation?

Caribbean Wine Tasting & Winery Tours with Instant Confirmation include: Private transportation to Montego Bay clubs and Street Food Barrel Aged Rhum Experience Customized Bar Hopping Tours From Montego Bay Resorts Shared Curacao East Side Tour and Liquor Tasting Artisan Puertorrican Winery and Distillery Tour View all Tours with Instant Confirmation →

Q: I need a ride! Which Caribbean Wine Tasting & Winery Tours have Hotel Pickup?

No problem. These Caribbean Wine Tasting & Winery Tours include Hotel Pickup: Private transportation to Montego Bay clubs and Street Food Customized Bar Hopping Tours From Montego Bay Resorts Nassau Guided City Tour Graycliff And Queen's Staircase City Sight Seeing with Wine, Rum Cake and Conch Fritter Samples Sunset Dinner at Bamboo Beach Club 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 transportation to Montego Bay clubs and Street Food

We apply a personal touch to tours, Ensuring that all guest remain safe while having fun. Flexibility and adaptation is also one of the key …More

Montego Bay, Jamaica

4.9 (15)

Private transportation to Montego Bay clubs and Street Food

We apply a personal touch to tours, Ensuring that all guest remain safe while having fun. Flexibility and adaptation is also one of the key...

2 hours Hotel pickup offered Free Cancellation

4.9 (15)

from
$18

Born in the Caribbean, inspired by Kentucky. We aged our world class rhum like some of the most famous bourbons in the world. Whether you’re …More

5.0 (4)

Barrel Aged Rhum Experience

Born in the Caribbean, inspired by Kentucky. We aged our world class rhum like some of the most famous bourbons in the world. Whether you’re...

1 hour 30 minutes Free Cancellation

5.0 (4)

from
$33

Customized Bar Hopping Tours From Montego Bay Resorts

Visit some of the city’s most lively bars and indulge in wine and cocktails. Experience Jamaicas own Red Stripe Beer. Also chill with the locals …More

Montego Bay, Jamaica

5.0 (3)

Customized Bar Hopping Tours From Montego Bay Resorts

Visit some of the city’s most lively bars and indulge in wine and cocktails. Experience Jamaicas own Red Stripe Beer. Also chill with the locals...

3 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$45

Shared Curacao East Side Tour and Liquor Tasting

Discover the vibrant history and stunning landscapes of Curacao on this 2-hour tour, complete with a unique liqueur tasting experience. Begin your adventure in Willemstad's …More

4.0 (2)

Shared Curacao East Side Tour and Liquor Tasting

Discover the vibrant history and stunning landscapes of Curacao on this 2-hour tour, complete with a unique liqueur tasting experience. Begin your adventure in Willemstad's...

2 hours Free Cancellation

4.0 (2)

from
$45

Artisan Puertorrican Winery and Distillery Tour

The visitor of PAPA PEDRO Wine & Distiller learn about the winery process. Also, the visitor learn about the distillery process. During the meeting can …More

5.0 (1)

Artisan Puertorrican Winery and Distillery Tour

The visitor of PAPA PEDRO Wine & Distiller learn about the winery process. Also, the visitor learn about the distillery process. During the meeting can...

1 to 2 hours Free Cancellation

5.0 (1)

from
$50

Learn to blend your own wine at one of the most unique experiences in the Bahamas. Come visit the oldest Church in the Bahamas to …More

4.8 (64)

Wine Maker Class at Bahama Barrels

Learn to blend your own wine at one of the most unique experiences in the Bahamas. Come visit the oldest Church in the Bahamas to...

1 hour 30 minutes Free Cancellation

4.8 (64)

from
$67

Nassau Guided City Tour Graycliff And Queen's Staircase

Experience Nassau Like Never Before with Exclusive City Tour. Embark on a journey through the vibrant streets of Nassau with exclusive city tour, offering a …More

Nassau, Bahamas

4.5 (59)

Nassau Guided City Tour Graycliff And Queen's Staircase

Experience Nassau Like Never Before with Exclusive City Tour. Embark on a journey through the vibrant streets of Nassau with exclusive city tour, offering a...

2 hours 30 minutes Hotel pickup offered Free Cancellation

4.5 (59)

from
$72

City Sight Seeing with Wine, Rum Cake and Conch Fritter Samples

Escape from the hustle and bustle of downtown and enjoy a two to three hour ride filled with wine, chocolate, rum cake and conch fritter …More

Nassau, Bahamas

4.7 (213)

City Sight Seeing with Wine, Rum Cake and Conch Fritter Samples

Escape from the hustle and bustle of downtown and enjoy a two to three hour ride filled with wine, chocolate, rum cake and conch fritter...

2 to 3 hours Hotel pickup offered Free Cancellation

4.7 (213)

from
$75

Enjoy a magical evening at Reggae Hill, as the sun sets over the White River and the warmth of small fires illuminate the riverbanks while …More

Ocho Rios, Jamaica

4.4 (5)

Exclusive Sunset Dinner At Reggae Hill

Enjoy a magical evening at Reggae Hill, as the sun sets over the White River and the warmth of small fires illuminate the riverbanks while...

4 hours Free Cancellation

4.4 (5)

from
$99

Enjoy a relaxed evening at Bamboo Beach Club with dinner by the sea, reggae music, and a casual atmosphere as the sun goes down. Small …More

Montego Bay, Jamaica

3.5 (2)

Sunset Dinner at Bamboo Beach Club

Enjoy a relaxed evening at Bamboo Beach Club with dinner by the sea, reggae music, and a casual atmosphere as the sun goes down. Small...

4 hours Hotel pickup offered Free Cancellation

3.5 (2)

from
$99

Rhythm Of Rum Tour & Rum Tasting Saint Lucia

This exciting feature begins at your location point (hotel or cruise terminal). Our journey will take us through the town of Castries and its environs …More

Castries, St Lucia

4.9 (13)

Rhythm Of Rum Tour & Rum Tasting Saint Lucia

This exciting feature begins at your location point (hotel or cruise terminal). Our journey will take us through the town of Castries and its environs...

3 hours Hotel pickup offered Free Cancellation

4.9 (13)

from
$100

This is a fun tour which entails sampling rum from local bars, We would then proceed to the beach for 2 hours, head to Fort …More

Kingstown, St Vincent and the Grenadines

5.0 (1)

RUM & FUN Tour

This is a fun tour which entails sampling rum from local bars, We would then proceed to the beach for 2 hours, head to Fort...

4 hours Free Cancellation

5.0 (1)

from
$110

Visit St. Lucia Distillers for a behind-the-scenes tour and tasting on this excursion from Roseau, St Lucia. Learn about how sugarcane is turned into rum …More

4.9 (10)

St. Lucia Rum Tasting and Tour

Visit St. Lucia Distillers for a behind-the-scenes tour and tasting on this excursion from Roseau, St Lucia. Learn about how sugarcane is turned into rum...

2 hours Hotel pickup offered Free Cancellation

4.9 (10)

from
$110

A fun, surprising and gourmet experience! 2 hours to discover the world of cheese, tasting 8 to 9 cheeses exclusively farm and artisan, selection of …More

4.9 (49)

Cheese and Wine Tasting

A fun, surprising and gourmet experience! 2 hours to discover the world of cheese, tasting 8 to 9 cheeses exclusively farm and artisan, selection of...

2 hours Free Cancellation

4.9 (49)

from
$111

Sint Maarten Wine Tasting Brewery Shopping and Jet-Blast Tour

Embark on a sensory journey with our Wine & Cheese Extravaganza, a delightful fusion of wine tasting, tapas indulgence, and brewery exploration! Begin your adventure …More

Philipsburg, St Maarten

4.6 (5)

Sint Maarten Wine Tasting Brewery Shopping and Jet-Blast Tour

Embark on a sensory journey with our Wine & Cheese Extravaganza, a delightful fusion of wine tasting, tapas indulgence, and brewery exploration! Begin your adventure...

4 to 5 hours Hotel pickup offered Free Cancellation

4.6 (5)

from
$130

Appleton Estate Rum Factory And YS Falls Inclusive Tours From Montego Bay

This is a hassle free Combine Tour to Ys falls and Appleton Rum Factory that leaves you with knowledge and memorable moments of our island. …More

Montego Bay, Jamaica

5.0 (5)

Appleton Estate Rum Factory And YS Falls Inclusive Tours From Montego Bay

This is a hassle free Combine Tour to Ys falls and Appleton Rum Factory that leaves you with knowledge and memorable moments of our island....

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$145

You will enjoy BEST Puerto Rico bars with a local. I know the best spots in Puerto Rico Monday to Monday. Great Cocktail drinks, beers …More

5.0 (9)

Old San Juan - Bar Hopping Private Tour

You will enjoy BEST Puerto Rico bars with a local. I know the best spots in Puerto Rico Monday to Monday. Great Cocktail drinks, beers...

2 to 3 hours

5.0 (9)

from
$145

St.Martin-St.Maarten: Small Group, History & Cheese Tasting Tour

St Martin has the remains of three forts of which two can be visited. Each fort offers a great view of one of the two …More

5.0 (4)

St.Martin-St.Maarten: Small Group, History & Cheese Tasting Tour

St Martin has the remains of three forts of which two can be visited. Each fort offers a great view of one of the two...

4 hours Free Cancellation

5.0 (4)

from
$159

Explore the vibrant culture of Saint Lucia on this engaging tour that includes a visit to a local rum distillery for a taste of handcrafted …More

Anse La Raye, St Lucia

5.0 (21)

St.Lucia Rum & Mud Bath Tour

Explore the vibrant culture of Saint Lucia on this engaging tour that includes a visit to a local rum distillery for a taste of handcrafted...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (21)

from
$167

Local Gourmet Bites & Wine Tasting - Night Activity in Curacao

Our Activity is best described as an upscale local culinairy experience complemented with an evening of wine tasting. We truly provide you with the local …More

5.0 (8)

Local Gourmet Bites & Wine Tasting - Night Activity in Curacao

Our Activity is best described as an upscale local culinairy experience complemented with an evening of wine tasting. We truly provide you with the local...

2 hours 30 minutes Free Cancellation

5.0 (8)

from
$175

Frequently Asked Questions

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

What are the best options for Caribbean Wine Tasting & Winery Tours?

What are the best kid-friendly options for Caribbean Wine Tasting & Winery Tours Tours?

Which Caribbean Wine Tasting & Winery Tours have Instant Confirmation?

Which Caribbean Wine Tasting & Winery Tours have Free Cancellation?

Caribbean Wine Tasting & Winery 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 Wine Tasting & Winery Tours have Hotel Pickup?

Got any more Caribbean trip ideas?

What are the most popular styles of Tours and Activities in Caribbean?