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Tours & Trips in Cuba in May 2026.

Visit destinations like Havanna, Trinidad, Cienfuegos, Santa Clara, Viñales, Varadero.

Cuba is the happy island in the Caribbean, with lots of Music, Salsa dancing, huge Cigars & great Rum, unspoiled white Beaches and old American Classic Cars... For a long time it has been on America's blacklist because of a communistic political system. For this reason you will not find (any) American company in Cuba: NO Mc Donalds Burgers, NO Kentucky Chicken, NO Pizza Hut, No Nothing. You'll love it!

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Cuba is a great travel destination. Unfortunately the island has become very isolated and is not receiving any oil from anyone. This energy crisis affects everything from daily blackouts to food shortages and cancelled flights. It is not recommended to travel to Cuba till further notice.

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Top Destinations in Cuba.

Below are our most visited cities, destinations and national parks in Cuba. Click on the city for more details of the destination.

Havanna

Havanna (13)

La Havana: capital and heart of Cuba, largest city in the Caribbean with 2mio people. Discover the culture, the music, the cars, the traditional bars and remainings of "the revolution" including Capitol and cigar factory.

Trinidad

Trinidad (12)

Trinidad is a really nice city with lots of colors and authenticity. Don't miss out on the Saturday night salsa dancing with great music. Local Amateurs act like professionals.

Viñales

Viñales (6)

Viñales is a small town in Pinar del Rio, known for the landscape and cigars.

Santiago De Cuba

Santiago De Cuba (2)

Santiago de Cuba is the second-largest city in Cuba and an important harbour. It is also home of the Cuban Revolution, Writers and Bacardi rum.

 

Search and compare Tours & Trips in Cuba. Book at the tour operator.

We have 4 tour operators that conduct 13 group tours and private tours in Cuba with duration 5 - 15 Days and rates starting at USD 999.

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Coming from:
United States
Languages:
English
Must see countries:
Cuba
Month:
May
  • globe International Operators (7)

All 7 International Tours and Cruises

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The Best of Western Cuba (Explore!)Google Map: The Best of Western Cuba

The Best of Western Cuba

preview
Group Tour

Soak up the atmosphere and vibrant culture of old Havana and Trinidad|Take in Vinales' spectacular landscape and relax on white-sand beaches|Visit the iconic Bay of Pigs Invasion Museum and Che Guevara's Mausoleum

From/To
Havanna (Round Trip)
Countries
Cuba
Operator
Explore!
Activities
tour category: Divingtour category: Boattour category: Walkingtour category: Nature
Duration
8 Days
Starting at
± USD 1,324
Operator
Explore!

Starting at

± USD 1,324

8 Days
Next Departure
23-May-2026
Details
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Cuba Explorer (G Adventures)Google Map: Cuba Explorer

Cuba Explorer

preview
Group Tour

Explore a side of Cuba that few rarely get to experience on this nine-day adventure. Cruise Havana’s history-infused streets in a classic car and stroll along Trinidad’s cobblestone avenues to the rhythms of music floating from open windows. Tour a tobacco plantation for a taste of iconic Cuban cult...

From/To
Havana ⇒ Havanna
Countries
Cuba
Operator
G Adventures
Activities
tour category: Boattour category: Walking
Duration
9 Days
Starting at
USD 1,499
Operator
G Adventures

Starting at

USD 1,499

9 Days
Next Departure
31-May-2026
Details
 
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Beautiful Cuba (Intrepid)Google Map: Beautiful Cuba

Beautiful Cuba

preview
Group Tour

From vintage cars to fragrant cigars, salsa your way from the colourful capital of Havana through the beautiful island of Cuba and surround yourself with history, music and mojitos in one of the world’s most unique places. Roll a cigar and sip rum with locals in the rural village of Vinales, feel th...

From/To
Havana (Round Trip)
Countries
Cuba
Operator
Intrepid Travel
Activities
tour category: Some bicycling is possibletour category: Walkingtour category: Nature
Duration
8 Days
Starting at
USD 1,940
Operator
Intrepid

Starting at

USD 1,940

8 Days
Next Departure
23-May-20264+
Details
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Cuba Discovery (On The Go)

Cuba Discovery

preview
Group Tour

Embark on a captivating 9-day tour across Cuba, where vibrant cities, stunning landscapes, and rich history await. Explore the charming streets of Havana, stroll through the Vinales Valley, and experience the timeless beauty of Trinidad. From the artistic mosaics of Fusterlandia to the historical Ba...

From/To
Havanna (Round Trip)
Countries
Cuba
Operator
On The Go Tours
Activities
tour category: Divingtour category: Walkingtour category: Nature
Duration
9 Days
Starting at
USD 1,985
Operator
On The Go

Starting at

USD 1,985

9 Days
Next Departure
21-May-20264+
Details
 
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Treasures of Cuba (G Adventures)Google Map: Treasures of Cuba

Treasures of Cuba

preview
Group Tour

The melody of horns floating through the air, classic cars parked in colonial squares, revolutionary statues — get over the resort wall and discover the real Cuba! Travel east to Santiago de Cuba and Baracoa and encounter the birthplace of Cuban rhythms and revolutionary fervour. Soak in Spanish her...

From/To
Havana ⇒ Havanna
Countries
Cuba
Operator
G Adventures
Activities
tour category: Divingtour category: Walkingtour category: Nature
Duration
15 Days
Starting at
USD 1,999
Operator
G Adventures

Starting at

USD 1,999

15 Days
Next Departure
23-May-2026
Details
Add to Favorites
Highlights of Havana (On The Go)

Highlights of Havana

preview
Group Tour

Discover the vibrant culture and history of Havana on this 5-day tour. Experience the charm of Old Havana, ride in classic cars, and explore local community projects. Visit the famous Fabrica de Arte Cubano and enjoy a scenic day trip to Vinales Valley, exploring tobacco fields and tasting local cof...

From/To
Havanna (Round Trip)
Countries
Cuba
Operator
On The Go Tours
Activities
tour category: Boattour category: Sailingtour category: Walking
Duration
5 Days
Starting at
USD 2,035
Operator
On The Go

Starting at

USD 2,035

5 Days
Next Departure
21-May-20264+
28-May-20264+
Details
 
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Active Cuba Adventure (On The Go)Google Map: Active Cuba Adventure

Active Cuba Adventure

preview
Group Tour

Enjoy an included 2-day hike in the Escambray Mountains and spend a day cycling through the Vinales Valley on this active 10-day Cuba group tour. You will also visit the Che Guevara Museum in Santa Clara, spend three nights in colonial Trinidad and visit the historic Bay of Pigs, scene of a US-backe...

From/To
Havanna (Round Trip)
Countries
Cuba
Operator
On The Go Tours
Activities
tour category: Horsetour category: Divingtour category: Some bicycling is possibletour category: Walkingtour category: Campingtour category: Safari
Duration
10 Days
Starting at
USD 2,365
Operator
On The Go

Starting at

USD 2,365

10 Days
Next Departure
26-May-20264+
Details