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Tours & Trips in Cuba in September 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 (14)

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.

Santiago De Cuba

Santiago De Cuba (5)

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.

Viñales

Viñales (3)

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

 

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

We have 3 tour operators that conduct 14 group tours and private tours in Cuba with duration 5 - 20 Days and rates starting at USD 845.

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Coming from:
United States
Languages:
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Must see countries:
Cuba
Month:
Sep
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  • globe International Operators (11)

All 11 International Tours and Cruises

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Best of West Cuba (On The Go)

Best of West Cuba

preview
Group Tour

Embark on this 6-day tour exploring the best of west Cuba, starting in Havana with its rich history and vibrant street life. Discover colourful art in Callejon de Hammel and Fusterlandia, then visit the creative community of Las Terrazas and the scenic mountain town of Soroa. Journey through the stu...

From/To
Havanna (Round Trip)
Countries
Cuba
Operator
On The Go Tours
Activities
tour category: Fishingtour category: Walking
Duration
6 Days
Starting at
USD 845
Operator
On The Go

Starting at

USD 845

6 Days
Next Departure
11-Sep-20264+
Details
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Cuban Rhythms: Beachfronts & Havana Vibes (G Adventures)Google Map: Cuban Rhythms: Beachfronts & Havana Vibes

Cuban Rhythms: Beachfronts & Havana Vibes

preview
Group Tour

For too many people, Cuba is nothing more than a beach resort. That’s crazy; the island practically buzzes with energy and you should do likewise — get moving. Journey through the culture-soaked streets of Trinidad and Old Havana for your fill of drinking and dancing. The music here pours out of ope...

From/To
Havana (Round Trip)
Countries
Cuba
Age Group
18 - 39 Years
Participants
Tours for Young Adults
Operator
G Adventures
Activities
tour category: Boattour category: Walking
Duration
8 Days
Starting at
USD 999
Operator
G Adventures

Starting at

USD 999

8 Days
Next Departure
06-Sep-2026
20-Sep-2026
Details
 
Add to Favorites
Best of Cuba (On The Go)

Best of Cuba

preview
Group Tour

Take in the best of Cuba in little more than a week on this 8-day escorted group tour, staying in charismatic local guesthouses as you go. Begin in the capital, Havana, with a guided tour, before continuing to Vinales and the historic Bay of Pigs. Explore the colonial cities of Cienfuegos and Trinid...

From/To
Havanna (Round Trip)
Countries
Cuba
Operator
On The Go Tours
Activities
tour category: Divingtour category: Walking
Duration
8 Days
Starting at
USD 1,055
Operator
On The Go

Starting at

USD 1,055

8 Days
Next Departure
09-Sep-20264+
23-Sep-20264+
Details
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Best of Cuba (Women Only) (On The Go)

Best of Cuba (Women Only)

preview
Group Tour

Join a women-only departure of our Best of Cuba tour! Take in the best of Cuba in little more than a week on this 8-day escorted group tour, staying in charismatic local guesthouses as you go. Begin in the capital, Havana, with a guided tour, before continuing to Vinales and the historic Bay of Pigs...

From/To
Havanna (Round Trip)
Countries
Cuba
Participants
Tour for women
Operator
On The Go Tours
Activities
tour category: Divingtour category: Walkingtour category: Female Travellers
Duration
8 Days
Starting at
USD 1,075
Operator
On The Go

Starting at

USD 1,075

8 Days
Next Departure
03-Sep-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
10-Sep-20264+
Details
Add to Favorites
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 (Round Trip)
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
26-Sep-2026
Details
 
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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
03-Sep-20264+
10-Sep-20264+
Details
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Cuba Uncovered (On The Go)

Cuba Uncovered

preview
Group Tour

Take in the best of Cuba on this 15-day, slow-paced tour, spending two nights in the majority of the country's top destinations. Enjoy a great mix of free time and included activities, and discover destinations including Havana, Trinidad and Santiago de Cuba. Learn more about the revolutionary figur...

From/To
Havanna (Round Trip)
Countries
Cuba
Operator
On The Go Tours
Activities
tour category: Boattour category: Walkingtour category: Train
Duration
15 Days
Starting at
USD 2,145
Operator
On The Go

Starting at

USD 2,145

15 Days
Next Departure
25-Sep-20264+
Details
 
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Cuban Cultural Adventure (On The Go)

Cuban Cultural Adventure

preview
Group Tour

Delve deeper into real Cuban culture, history and life on this 9-day group tour, staying in charismatic local guesthouses. Enjoy guided sightseeing in Havana, Trinidad, Vinales and Cienfuegos and discover the historic Bay of Pigs. Watch a cannon blast ceremony at Havana Harbour, meet local organic f...

From/To
Havanna (Round Trip)
Countries
Cuba
Operator
On The Go Tours
Activities
tour category: Walkingtour category: Cooking
Duration
9 Days
Starting at
USD 2,535
Operator
On The Go

Starting at

USD 2,535

9 Days
Next Departure
06-Sep-20264+
20-Sep-20264+
Details
Add to Favorites
Cuba Encompassed (On The Go)

Cuba Encompassed

preview
Group Tour

Discover Eastern and Western Cuba on this 20-day Cuba group tour, our most comprehensive tour of the Caribbean island. Begin in the capital of Havana, before moving on to revolutionary Santa Clara, and the culturally-rich Bayamo. Journey through the mountains of Segundo Frente, coastal Baracoa, and ...

From/To
Havanna (Round Trip)
Countries
Cuba
Operator
On The Go Tours
Activities
tour category: Boattour category: Walkingtour category: Naturetour category: Train
Duration
20 Days
Starting at
USD 2,985
Operator
On The Go

Starting at

USD 2,985

20 Days
Next Departure
25-Sep-20264+
Details