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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!

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

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

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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.

Coming from:: United States
Languages:: English
Must see countries:: Cuba
Month:: Sep

International Operators (11)
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All 11 International Tours and Cruises

Picture for Tour 89228

Best of West Cuba

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From/To: Havanna (Round Trip)
Countries: Cuba
Operator: On The Go Tours
Tour Type: Group Tours
Activities

Duration: 6 Days
Starting at: USD 845
Operator: On The Go

Starting at

USD 845

6 Days

Next Departure

11-Sep-2026

4+

Picture for Tour 2482

Google Map: Cuban Rhythms: Beachfronts & Havana Vibes

Cuban Rhythms: Beachfronts & Havana Vibes

preview

From/To: Havanna (Round Trip)
Countries: Cuba
Age Group: 18 - 39 Years
Participants: Tours for Young Adults
Operator: G Adventures
Tour Type: Group Tours
Activities

Duration: 8 Days
Starting at: USD 999
Operator: G Adventures

Starting at

USD 999

8 Days

Next Departure

06-Sep-2026
20-Sep-2026

Picture for Tour 89227

Best of Cuba

preview

From/To: Havanna (Round Trip)
Countries: Cuba
Operator: On The Go Tours
Tour Type: Group Tours
Activities

Duration: 8 Days
Starting at: USD 1,055
Operator: On The Go

Starting at

USD 1,055

8 Days

Next Departure

09-Sep-2026	4+
23-Sep-2026	4+

Picture for Tour 89226

Best of Cuba (Women Only)

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From/To: Havanna (Round Trip)
Countries: Cuba
Participants: Tour for women
Operator: On The Go Tours
Tour Type: Group Tours
Activities

Duration: 8 Days
Starting at: USD 1,075
Operator: On The Go

Starting at

USD 1,075

8 Days

Next Departure

03-Sep-2026

4+

Picture for Tour 89231

Cuba Discovery

preview

From/To: Havanna (Round Trip)
Countries: Cuba
Operator: On The Go Tours
Tour Type: Group Tours
Activities

Duration: 9 Days
Starting at: USD 1,985
Operator: On The Go

Starting at

USD 1,985

9 Days

Next Departure

10-Sep-2026

4+

Picture for Tour 2479

Google Map: Treasures of Cuba

Treasures of Cuba

preview

From/To: Havana ⇒ Havanna
Countries: Cuba
Operator: G Adventures
Tour Type: Group Tours
Activities

Duration: 15 Days
Starting at: USD 1,999
Operator: G Adventures

Starting at

USD 1,999

15 Days

Next Departure

26-Sep-2026

Picture for Tour 89236

Highlights of Havana

preview

From/To: Havanna (Round Trip)
Countries: Cuba
Operator: On The Go Tours
Tour Type: Group Tours
Activities

Duration: 5 Days
Starting at: USD 2,035
Operator: On The Go

Starting at

USD 2,035

5 Days

Next Departure

03-Sep-2026	4+
10-Sep-2026	4+

Picture for Tour 89233

Cuba Uncovered

preview

From/To: Havanna (Round Trip)
Countries: Cuba
Operator: On The Go Tours
Tour Type: Group Tours
Activities

Duration: 15 Days
Starting at: USD 2,145
Operator: On The Go

Starting at

USD 2,145

15 Days

Next Departure

25-Sep-2026

4+

Picture for Tour 89234

Cuban Cultural Adventure

preview

From/To: Havanna (Round Trip)
Countries: Cuba
Operator: On The Go Tours
Tour Type: Group Tours
Activities

Duration: 9 Days
Starting at: USD 2,535
Operator: On The Go

Starting at

USD 2,535

9 Days

Next Departure

06-Sep-2026	4+
20-Sep-2026	4+

Picture for Tour 89232

Cuba Encompassed

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From/To: Havanna (Round Trip)
Countries: Cuba
Operator: On The Go Tours
Tour Type: Group Tours
Activities

Duration: 20 Days
Starting at: USD 2,985
Operator: On The Go

Starting at

USD 2,985

20 Days

Next Departure

25-Sep-2026

4+

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