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: Luxury Private Picnic in Paradise Beach Floyd's Pelican Bar St.Martin-St.Maarten: Small Group, History & Cheese Tasting Tour Sint Maarten Wine Tasting Brewery Shopping and Jet-Blast Tour 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: Luxury Sunset Beach Proposal in Nassau Bahamas Luxury Private Sunset Cruise for up to 6 guests Island Insider || Concierge Services Sunset cruises Cigar Rolling Lesson and Wine Blending Class View all Tours with Instant Confirmation →

Q: 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: Private Luxury Dinner Sunset Cruise in St. Lucia Luxury Sunset Beach Proposal in Nassau Bahamas Luxury Private Sunset Cruise for up to 6 guests Island Insider || Concierge Services Sunset cruises View all Tours with Free Cancellation →

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 Luxury Dinner Sunset Cruise in St. Lucia Luxury Sunset Beach Proposal in Nassau Bahamas Cigar Rolling Lesson and Wine Blending Class Luxury Private Picnic in Paradise Beach Floyd's Pelican Bar 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 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

At Love Curated, we offer one of the only fully tailored luxury beach proposal experiences in Nassau, designed specifically for vacationing couples. We transform your …More

Nassau, Bahamas

5.0 (4)

Luxury Sunset Beach Proposal in Nassau Bahamas

At Love Curated, we offer one of the only fully tailored luxury beach proposal experiences in Nassau, designed specifically for vacationing couples. We transform your...

3 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$1,250

Luxury Private Sunset Cruise for up to 6 guests

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us …More

5.0 (38)

Luxury Private Sunset Cruise for up to 6 guests

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us...

2 hours Free Cancellation

5.0 (38)

from
$695

From a visit to historical sites ,to a trip to the local supermarket, how about a corporate meeting or a gourmet supper while watching the …More

5.0 (3)

Island Insider || Concierge Services

From a visit to historical sites ,to a trip to the local supermarket, how about a corporate meeting or a gourmet supper while watching the...

3 hours Free Cancellation

5.0 (3)

from
$650

Relax and unwind as you experience a sightseeing cruise throughout Nassau harbor and along the western coastline to Sandyport, as you watch a beautiful sunset …More

4.0 (4)

Sunset cruises

Relax and unwind as you experience a sightseeing cruise throughout Nassau harbor and along the western coastline to Sandyport, as you watch a beautiful sunset...

2 hours Free Cancellation

4.0 (4)

from
$600

Cigar Rolling Lesson and Wine Blending Class

Remember your time in the Bahamas with your own unique wine blend, corked and labeled by you as well as a cigar rolled with your …More

Nassau, Bahamas

5.0 (1)

Cigar Rolling Lesson and Wine Blending Class

Remember your time in the Bahamas with your own unique wine blend, corked and labeled by you as well as a cigar rolled with your...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$436

Willemstad Culinary Adventure: Private 3-Hour Foodie Tour

Experience Curacao with all the five senses savoring its unique cuisine at three personally and carefully chosen restaurants in historical Willemstad. At each restaurant there …More

5.0 (10)

Willemstad Culinary Adventure: Private 3-Hour Foodie Tour

Experience Curacao with all the five senses savoring its unique cuisine at three personally and carefully chosen restaurants in historical Willemstad. At each restaurant there...

3 hours Free Cancellation

5.0 (10)

from
$375

Award yourself with a unique, quintessential retreat, offering a tropical once in a lifetime memory, taking al fresco dinning to a Caribbean Paradise! Started in …More

Grand Case, St Maarten

4.4 (9)

Luxury Private Picnic in Paradise Beach

Award yourself with a unique, quintessential retreat, offering a tropical once in a lifetime memory, taking al fresco dinning to a Caribbean Paradise! Started in...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.4 (9)

from
$253

Aruba Private Sip and Paint Experience for Couples

Island Inspirations by VL, a locally-owned business, presents Aruba's Finest Sip and Paint Experience. Tap into your artistic side with a burst of creativity and …More

4.5 (4)

Aruba Private Sip and Paint Experience for Couples

Island Inspirations by VL, a locally-owned business, presents Aruba's Finest Sip and Paint Experience. Tap into your artistic side with a burst of creativity and...

2 hours Free Cancellation

4.5 (4)

from
$195

Can you imagine having fresh lobsters with some ice cold red stripe beer in the middle of the ocean watching the beautiful sunset in the …More

Negril, Jamaica

3.0 (1)

Floyd's Pelican Bar

Can you imagine having fresh lobsters with some ice cold red stripe beer in the middle of the ocean watching the beautiful sunset in the...

4 to 6 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$185

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

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

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

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

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

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

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

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

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