Cuba is the only place where a 1950s Chevrolet counts as public transport. It’s also an island of salsa spilling out of doorways at noon, tobacco farmers who roll you a cigar while explaining exactly why theirs is better, colonial towns painted every colour in the box and a revolutionary history on every street corner. It is not, it must be said, the easiest country to travel independently, which is precisely why a good tour earns its keep here.
Our Cuba tours come in three flavours: a week or so in the west and centre, the full length of the island to Baracoa and Santiago, and cycling trips with a support van for the hills. This guide compares them all, with who each suits and its honest drawback.
The quick answer
- If you want the highlights in a week at a good price, pick Beautiful Cuba.
- If you want the same route with better rooms and a classic-car tour, pick the Cuba Small Group Tour.
- If you want the whole island, east to Baracoa, pick Best of Cuba.
- If you want to cycle, pick Western Cuba (7 days), Cuba East (8 days) or Cycle Cuba (14 days).
Every Cuba tour compared
| Tour | Days | Price from | Physical rating | Group size | Flights included | Best for |
|---|---|---|---|---|---|---|
| Touring | ||||||
| Beautiful Cuba: Havana, Viñales & Trinidad – 8 Days | 8 | £1,195 pp | Low | Max 12 | No | First-timers, great value |
| Cuba Small Group Tour: Havana, Viñales, Trinidad & Cienfuegos – 9 Days | 9 | £2,585 pp | Low | Max 12 | No | Better rooms, more included |
| Best of Cuba: Havana, Baracoa, Santiago & Trinidad – 15 Days | 15 | £1,670 pp | Low | Max 16 | No | The whole island |
| Cycling | ||||||
| Cycling in Western Cuba: Havana, Viñales & Cayo Jutías – 7 Days | 7 | £875 pp | Medium | Max 16 | No | A week in the west |
| Cycle Cuba East: Cienfuegos, Trinidad & Varadero – 8 Days | 8 | £1,060 pp | Medium | Max 16 | No | The centre and Varadero |
| Cycle Cuba: Viñales, Bay of Pigs, Trinidad & Varadero – 14 Days | 14 | £1,875 pp | Medium | Max 16 | No | West to east, two weeks |
Prices are per person, twin share, live from our tour pages (updated November 2026). The lowest price can apply to a later departure, so check the dates you want on each tour page.
First, a word about where you stay
Almost every Cuba tour stays in casas particulares, family-run guesthouses with private en-suite rooms and air-conditioning. Far from a compromise, they’re often the highlight: breakfast cooked by your hosts, rocking chairs on the terrace and an insider’s view of Cuban life you’d never get in a hotel. Larger groups are sometimes split between neighbouring houses. Only the Small Group Tour adds a hotel, in Havana.
Touring: the west, the centre and the whole island
Beautiful Cuba: the highlights in a week
Beautiful Cuba: Havana, Viñales & Trinidad – 8 Days
- 8 days
- From £1,195 per person
- Max 12 people
- Starts and ends in Havana, Cuba
- Physical rating: low
- Flights not included
- Year-round departures
Eight days with a local leader and up to 12, by private transport. A walk round Old Havana, the orchid garden at Soroa, two nights in Viñales with a walk through the tobacco farms among the limestone mogotes and a farm-to-table dinner, a swim at the Bay of Pigs, elegant Cienfuegos, two nights of cobbled streets and live music in Trinidad, and the Che Guevara memorial in Santa Clara on the way back to Havana.
Suits: first-timers who want the classic loop and a taste of home life. The honest drawback: some long drives, and only a handful of meals beyond breakfast.
Cuba Small Group Tour: the upgraded version
Cuba Small Group Tour: Havana, Viñales, Trinidad & Cienfuegos – 9 Days
- 9 days
- From £2,585 per person
- Max 12 people
- Starts and ends in Havana, Cuba
- Physical rating: low
- Flights not included
- Departures in January, February, March, April, May, July, October, November, December
Nine days, upgraded, with a local leader and no more than 12. You start with a convoy of classic American cars along the Malecón to Revolution Square, then Old Havana, a fruit workshop and the Soroa orchid garden, Viñales with a valley walk and tobacco farm, a salsa class, the Bay of Pigs, Cienfuegos, two nights in Trinidad with dinner with a local family and the Valle de los Ingenios, and Santa Clara. Havana is in a characterful hotel and the rest in premium guesthouses with large rooms, with tips covered.
Suits: first-timers who want comfort in a country where good rooms are scarce. The honest drawback: it costs considerably more than Beautiful Cuba for a similar route, and many guesthouses have stairs and no lift.
Best of Cuba: the full island
Best of Cuba: Havana, Baracoa, Santiago & Trinidad – 15 Days
- 15 days
- From £1,670 per person
- Max 16 people
- Starts and ends in Havana, Cuba
- Physical rating: low
- Flights not included
- Year-round departures
Fifteen days the length of Cuba and back, with a local leader and up to 16. Old Havana, Che Guevara’s mausoleum in Santa Clara, a jewellery workshop for young people in Ciego de Ávila, Bayamo, two nights in remote Baracoa with a cocoa plantation and the Yumurí canyon, two nights in Santiago de Cuba with its music and the Basilica of El Cobre, Camagüey by bicycle taxi, Trinidad and Cienfuegos.
Suits: history and music lovers who want the real, whole Cuba on a budget. The honest drawback: long travel days, breakfast only, and Viñales is not included.
Cuba by bike
Cuba’s quiet country roads, where traffic often means a horse and cart, make it surprisingly good for cycling. All three trips use hybrid bikes and a support vehicle that carries your luggage, covers the longer stretches and is always there when the heat wins.
Cycling in Western Cuba: a week in the green west
Cycling in Western Cuba: Havana, Viñales & Cayo Jutías – 7 Days
- 7 days
- From £875 per person
- Max 16 people
- Starts and ends in Havana, Cuba
- Physical rating: medium
- Flights not included
- Departures in January, February, March, April, July, October, November, December
Seven days with a leader, a support crew and up to 16 riders aged 15 and over. A ride through Havana past John Lennon Park and the Capitol, a guided walk round Old Havana’s four plazas, two nights at Soroa with its orchid garden and Las Terrazas, the Los Portales cave, a tobacco farm in Viñales and the beach at Cayo Jutías.
Suits: active first-timers with some cycling experience. The honest drawback: no Trinidad, and a few short climbs.
Cycle Cuba East: the centre and Varadero
Cycle Cuba East: Cienfuegos, Trinidad & Varadero – 8 Days
- 8 days
- From £1,060 per person
- Max 16 people
- Starts and ends in Havana, Cuba
- Physical rating: medium
- Flights not included
- Departures in January, February, March, April, July, October, November, December
Eight days with a local leader and a support vehicle. You ride along the Bay of Pigs to Cienfuegos, on to colonial Trinidad, up through the tropical hills to Santa Clara and the Che Guevara memorial, then to Varadero for a free day on its long white beach before the final stretch towards Havana. Most lunches are included.
Suits: keen cyclists and returning visitors. The honest drawback: it’s hot and not for anyone new to cycling.
Cycle Cuba: west to east in two weeks
Cycle Cuba: Viñales, Bay of Pigs, Trinidad & Varadero – 14 Days
- 14 days
- From £1,875 per person
- Max 16 people
- Starts and ends in Havana, Cuba
- Physical rating: medium
- Flights not included
- Departures in January, April, July, October, November, December
Fourteen days, combining both: the west with Soroa, Las Terrazas, the Los Portales cave and Viñales, then Cienfuegos, the Bay of Pigs, Trinidad, the cloud forest of Topes de Collantes, Santa Clara and two nights in Varadero. Eleven breakfasts, eight lunches and three dinners are included, and families with teenagers aged 14 and over are welcome.
Suits: active travellers who want rural Cuba properly. The honest drawback: some hills, and no Santiago or the far east.
How to choose
By time. A week: Beautiful Cuba, the Small Group Tour, Western Cuba and Cuba East by bike. Two weeks: Best of Cuba or Cycle Cuba.
By route. The west and centre (Havana, Viñales, Trinidad): Beautiful Cuba, the Small Group Tour and the 14-day bike trip. The whole island, including Santiago and Baracoa: Best of Cuba.
By budget. The cycling trips, Beautiful Cuba and Best of Cuba are excellent value. The Small Group Tour costs the most, for better rooms and more included. Live prices are in the table above.
By fitness. The touring trips are rated low; the cycling trips are rated medium.
When to go
The dry season, from about November to April, is the best time, with warm days and lower humidity. Summer is hot and humid, and the hurricane season runs from about June to November, peaking in September and October. Most of these tours run in the cooler months; the months for each are in its fact panel above.
You’ll need a Cuban tourist card (a visa) and proof of travel insurance to enter Cuba. Neither is included in these tours, and we can help with the tourist card. Check the FCDO travel advice for Cuba before you travel.
Frequently asked questions
What is the best Cuba tour for first-time visitors?
Beautiful Cuba covers Havana, Viñales, Cienfuegos and Trinidad in eight days. For more comfort, try the Cuba Small Group Tour.
Which Cuba tour covers the whole island?
Best of Cuba travels from Havana to Baracoa and Santiago de Cuba and back in 15 days.
Can I cycle in Cuba?
Yes, Cycling in Western Cuba, Cycle Cuba East and Cycle Cuba all have a support vehicle and hybrid bikes. They are rated medium.
Where do you stay on a Cuba tour?
Mostly in casas particulares, family-run guesthouses with private en-suite rooms and air-conditioning. The Small Group Tour uses a hotel in Havana and premium guesthouses elsewhere.
Do I need a visa for Cuba?
UK visitors need a Cuban tourist card and proof of travel insurance. Check the FCDO travel advice for the latest rules.
Are flights included?
No, all of these tours are land-only, and we can arrange flights to Havana.
Ready for Cuba?
Tell us whether you'd rather ride in a classic car or on a bicycle, and a Travelisto specialist will compare the Cuba tours with you.
Keep planning
Prices are live from our tour pages (updated November 2026). Tour details and dates can change; your specialist will confirm everything before you book.
