Cuba Guided Walking Holiday

Explore this colourful island with a fascinating history


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Activity types:

  • Central location
  • Culture
  • Flora


  • 2
More information

Choosing the level of your walks

Our easy grading system shows whether a region offer gentle strolls or more challenging routes to help you choose the right holiday for you. Difficulty is measured on many factors such as distance, ascent/descent, terrain, weather and more. There's no magic formula, but from our experience we grade our walks 1 to 5 (where 1 is easy and 5 hard). Our challenger holidays require a high level of fitness and stamina.

More about difficulty levels

From £3,248.00 - 14 nights


Special offer: DEAL OF THE WEEK: 4 Nov 2019 save £500 Per Couple

Prices are per person

Room 1:
Room 2:
Room 3:

Holiday overview

Download Cuba 2019 Trip Notes

The cobbled colonial streets of Havana, Cienfuegos and Trinidad stretch out before you, winding their way through peaceful plazas filled with cultural cues from Spanish, African, French and Asian influences. The tobacco fields and rainforests of Viñales contribute a rich biodiversity, while the peaks, waterfalls, white sand beaches and plantations of central and western Cuba offer a more challenging exploration.

Holiday highlights

  • Take a walking tour of historic Habana Vieja and explore the city in a classic Chevrolet
  • Walk in Viňales among limestone ‘mogotes’, tobacco fields and rainforest
  • Go in search of the perfect cigar and learn how to roll a tobacco criollo with an expert
  • Follow in the footsteps of Hemingway and discover his favourite haunts
  • Debate the legacy of Che Guevara and revolutionary history in Santa Clara
  • Explore the Caribbean coast in the Northern Cays and enjoy a dose of barefoot luxury
  • Walk out on senderos in Cuba’s countryside to reveal the timeless heart of the country
  • Discover Trinidad, a Spanish colonial treasure frozen in time
  • Enjoy a stay in a homestay (casas particulares) for an authentic Cuban experience

Price includes

  • 14 nights’ accommodation in en-suite rooms
  • Full board from dinner on arrival to breakfast on departure, less one lunch and one dinner*
  • A full programme of guided walks led by local guides and an HF Holidays' leader
  • All sightseeing and entrance fees
  • Travel by private, air-conditioned coach/minivan 
  • Tips
*Except April departure, owing to flight times

In pictures...


We stay in a range of accommodation during our holiday in Cuba: from authentic and welcoming Cuban homestays, to iconic hotels and luxury 5* resorts.

Hotel-Nacional in Cuba

Hotel Nacional

Hotel-Capri in Cuba

Hotel Capri

Havana - Hotel Capri or Notel Nacional

Our hotel is located in the middle of the Vedado district of Havana, overlooking the harbour, seawall and city. A magical setting, and an excellent introduction to Cuba. The hotel is likely to be the Hotel Capri or the Hotel Nacional.

Los-Jazmines in Cuba

Viñales Valley - Los Jazmines

Our accommodation in the beautiful Viñales Valley; its comfortable rooms and pool make the perfect place to relax after our walks. If we are not in Los Jazmines, then we'll be staying at Casas Particulares (bed & breakfast) with evening meals in local Paladars.

La-Granjita in Cuba

Santa Clara - Hotel La Granjita

We'll then travel to Santa Clara where we'll be at Hotel La Granjita.

Exterior view of Hotel Iberostar, Cuba

Cayo Santa Maria - Hotel Iberostar Cayo Los Ensenachos

This is a luxury, all-inclusive 5* hotel resort on the northern coast of Cuba. Within a short distance of some of the island's finest beaches, you're sure to enjoy spending time here relaxing before your journey continues.

Casas-Particulares in Trinidad, Cuba

Trinidad - Casas Particulares

At Casas Particulares we enjoy wonderful local hospitality and get a real insight into Cuban culture. Guests will be accommodated in different properties on the same street, those booked in a single room will be staying in a house where other HF guests are staying. All bedrooms have en-suite bathrooms with hot and cold water. They have fans and/or air conditioning. Each house will have its own character and will be decorated according to the tastes of their owner. Food will be hearty home cooking and breakfasts will be in the house where you sleep. Dinner will be in different homes/restaurants each evening. Please note, it is likely that beds may not be made during your stay.

Hotel-Faro-Luna in Cuba

Cienfuegos - Hotel Faro Luna

On to the modern facilities and city scenes of Hotel Faro Luna or similar at Cienfuegos.

Exterior of Iberostar Havana, Cuba

Havana - Hotel Iberostar Parque Central

Right in the urban heart of Havana, we end our holiday at the Hotel Iberostar Parque Central, an elegant 5* hotel with colonial-style architecture.

Cuba's infrastructure cannot be compared to that of other Caribbean destinations. While city hotels are generally good 3 and 4-star standard (this is Cuban star rating), accommodation in rural areas is in guesthouses, where the facilities are more basic. Despite Cuba's increasing popularity, it is still a developing country and some of the accommodation is not of a standard that is perhaps expected from a Caribbean destination. The accommodation is all air conditioned and in excellent locations.

As Cuba becomes more popular, hotels are only confirmed 2 or 3 days prior to travel. Even then, things could change during the tour. Many of the hotel facilities are still as they were 60 years ago, and slowly money is only just now being invested in improving the hotels or the infrastructure. If you can see past the accommodation problems, and really travel with a sense of adventure, then we're sure the locals and the scenery will more than win you over.

Although we use the best available hotels in these areas, standards of service can be leisurely, but this is easily compensated by the warm welcome and Cuba's unique culture and scenery.


Guided Walking & Sightseeing in Cuba

Download Cuba 2019 Trip Notes

Walks are 2-7 miles (3 - 10km) with ascents of up to 1,000 feet (300m). Travelling days include sightseeing stops or short walks.

Days 1-2: Outward flight & Havana

Havana CubaFly to Havana and transfer to the hotel for 2 nights.

The next day, take a morning walking tour of the historic old centre of Havana, visiting the Plaza de Cathedral, Plaza Vieja and the old city walls. We'll also visit the Havana Rum Museum for a chance to learn more about this typically Caribbean tipple and enjoy a taste or two.

After lunch in the city, we'll travel to Finca Vigia, lovingly kept as it was when Ernest Hemingway lived here. We'll continue on to Cojimar and explore the Hemingway connections here.

In the evening, enjoy a cocktail making class and a tapas dinner.

Days 3-4: Viňales Valley - Cuban Tobacco Country

Vinales Valley CubaDrive west into the beautiful Viňales valley, a picturesque region of small farms and old tobacco plantations. On arrival, we'll enjoy a light lunch on a typical Cuban farm then learn how to roll a 'tabaco criollo', the local cigar. This afternoon, walk in the unusual scenery of limestone ‘mogotes’ on the Palmarito trail, which leads through small villages with a traditional way of life. We continue to Viñales, where we stay for for 2 nights. Enjoy an evening walk on the Sendero Valle del Silencio and dinner on a local farm, high above the town to enjoy the sunset. 

The next day we set off early to walk on the Acuaticos trail, heading into the hills in time for sunrise over the Viñales Valley. We then set off into the heart of Cuban tobacco country and the provincial capital, Pino del Rio, for a visit to a tobacco factory and a nearby tobacco farm, where we'll have lunch, to learn the delicate art of producing top-quality tobacco.

Days 5: Santa Clara

Santa Clara CubaWe set off towards Central Cuba to Santa Clara, stopping en route to visit Las Terrazas Biosphere Reserve and to walk along the La Serafina trail, showcasing the native and migratory birdlife. We continue to Santa Clara after lunch, where we'll visit the Che Guevara memorial, resting place for Che and sixteen of his men who were killed in action in 1967 CE in Bolivia. We may visit the memorial on Day 6. Stay in Santa Clara for 1 night.

Days 6-7: Remedios and the Northern Cays of Cuba

Trinidad CubaWe depart Santa Clara for the city of Remedios. The town is one of the oldest in Cuba, and the 17th century colonial architecture is impressive to say the least. Remedios is a National Monument town and we'll enjoy a walking tour of the historic centre, including the colonial church, Iglesia Mayor with its beautifully decorated gold altars.

We continue our journey to the Northern Cays of Cuba, where we'll stay in Cayo Santa Maria for 2 nights.

Day 7 is a free day for you to relax, enjoy the hotel's facilities or explore the nearby area - perhaps a swim in the Caribbean sea or a short walk through the nearby tropical woodland.

Days 8-10: Trinidad

Cienfuegos CubaWe begin our journey to Trinidad, stopping en route to walk in the Escambray Mountains. From the village of Jibacoa, we set off along the banks of the Hanabanilla Reservoir, walking through coffee and fruit plantations. We'll enjoy lunch at La Gallega ranch and continue to Trinidad, where we stay for 3 nights.

The next day we'll explore historic Trinidad town and visit the Valley of Sugar mills, through the remnants of large sugar plantations. This evening is free for you to explore Trinidad's many paladar restaurants and enjoy the colourful evening atmosphere.

Day 10 is a free day for you to explore the town and local area at leisure. You might like to take a Catamaran tour, explore Trinidad further or simply relax. We'll eat together as a group in the evening at a local paladar.

Days 11-12: Cienfuegos

After breakfast we drive to Hanabanilla to stretch our legs around the Hanabanilla Reservoir on the Trek la Atalaya trail. After lunch, we transfer to Cienfuegos, a town settled by French immigrant descendants more than 150 years ago, and check into our hotel for 2 nights. 

The next day's excursion visits the Cienfuegos Botanical Garden. Visit the Orchid Garden Macradenia, Palmira, and an orchard. We leave the garden and enjoy this beautiful town. Cienfuegos is one of Cuba’s most charming cities. Set on the shores of a huge natural bay, the city was originally one of Cuba’s most important harbours. Settled by French immigrants fleeing the slave uprisings of Haiti, the city has elegant boulevards and classical homes, as well as spacious squares and one of Cuba’s most famous theatres, Teatro Terry. We'll visit the theatre and the main square during our time here.

Days 13-14: Havana

Havana CubaWe return to Havana for 2 nights, driving via the Zapata swamp and a stop in Caleta Buena to have lunch, with time to swim in the sea. We continue to the Bay of Pigs, stopping at the Playa Giron (Bay of Pigs) Museum to learn about US involvement in the anti-Catro movement. We drive on to Havana, and enjoy an evening guided walk on Havana’s atmospheric waterfront promenade, the Malecon. We'll enjoy a cocktail at El Floridita, one of Hemingway's favourite haunts, before enjoying a special dinner together.

The following day we have free time during the day, where you can further explore the many sights of Havana. In the evening, enjoy a tour of the city in an American classic car before a final dinner. You might then enjoy time in a local bar to hear some typical Cuban sounds and maybe a dance or two!

Days 15: Return flight

Transfer to the airport for our overnight flight to the UK.

General Information


British nationals require a full valid passport with six months validity from the date of departure from Cuba, and a visa or tourist card to enter Cuba. Other passport holders please check with your nearest Cuban embassy or consulate for entry requirements.


For UK passport holders, the Tourist Card is included in the price of your holiday. This will be sent to you with your final despatch, 2-3 weeks before departure. Those who do not have British passports with full right of residence in the UK should check requirements with a Cuban Embassy or Consulate.

Health Advice

Before booking, you should check with your doctor to see if any health precautions are needed. The following websites provide a wealth of information on travelling and health:

Vaccines: Hepatitis A & Tetanus vaccinations are recommended. Diphtheria, Rabies and Typhoid are sometimes recommended too. Dengue fever and meningitis may also occur.

General standards of health and health services in Cuba are of a high standard. However, there is no reciprocal agreement with the UK. As with all international travel, medical insurance is essential.

Cuban authorities have strengthened their health screening at entry ports; if you show symptoms of a temperature or infectious disease you may be subjected to a medical examination. The Cuban authorities are carrying out chemical fumigation across the island to control the spread of mosquito-borne diseases; the chemicals used may cause some discomfort if you come into contact with them.


Temperatures in Cuba are fairly constant year-round with sub-tropical heat being cooled by north-easterly trade winds. Average temperatures are 27°C (81°F) in February and 26°C (78°F) in November; these are averages only and could be higher. Cuba has 80% humidity year-round and a wet season running from May to September and this is the main hurricane season.


Vegetarianism is a relatively new concept in this part of the world, and vegetarian cuisine is therefore rather basic. Fish, chicken and pork are the most common options, meals in Cuba can sometimes be rather bland and choices can sometimes be limited. In general we do our best to accommodate dietary requirements, but it is important for travellers to Cuba to realise that there are limitations on food variety and food can be repetitive. You may wish to consider bringing some snacks with you.


There is a dual currency system in operation in Cuba, and tourists and foreign visitors are required to use the Convertible Peso (CUC). Cuban Pesos, or ‘moneda nacional’, can be used in small shops, cafeterias and street stalls away from the tourist centres, although this is a rare occurence. The import and export of local currency is prohibited.

Since 2004 US Dollars are no longer legal tender in Cuba. It is possible to exchange US Dollars cash but there are charges of around 20% to do so. MasterCard and Visa are increasingly accepted, provided they are not issued by a US bank, or a bank with links to the USA, but hefty fees are often added. ATMs are more common but not everywhere.

Pounds Sterling, Euros and Canadian Dollars are readily changeable. CUC notes can be exchanged for other currencies on departure at the airport.

Credit cards can be taken as back-up although they incur a commission of over 10%. Travellers' cheques are not advised.


Tips are included on this holiday.

For flights information please see the Dates and Prices tab


Peter Shortt

Peter has travelled extensively around the mountain countries of the world. His favourite places are the Anti Atlas in Morocco and the Himalayas, both for their outstanding views but also for the cultural differences he enjoys sharing with guests. A later interest in life has come through exploring the economic and cultural changes taking place in old communist countries such as Vietnam and Cuba, and trying out his salsa steps. In his spare time he volunteers as a leader for the Duke of Edinburgh Award Scheme.

He has worked as a guide and instructor in one form or another for most of has life and led for HF Holidays since 2001.

Peter is leading our November 2019 holiday.


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Dates & Prices

Here at HF Holidays, we pride ourselves in offering a unique holiday full of experiences that you can’t find with anyone else. Find out what's included in this holiday.

Date Description Nights Brochure price Buy today for Book
4 Nov 2019 CUWHW - Cuba
(Travel included - Departs from: London Gatwick)

Flight - Outbound


  • Depart: 4 Nov 2019, 12:30 p.m.
  • Arrive: 4 Nov 2019, 5:40 p.m.
  • Depart from: London Gatwick
  • Arrive at: Havana Jose Marti International

Flight - Return


  • Depart: 18 Nov 2019, 8:10 p.m.
  • Arrive: 19 Nov 2019, 9:50 a.m.
  • Depart from: Havana Jose Marti International
  • Arrive at: London Gatwick
14 £3,999.00 £3,748.00 DEAL OF THE WEEK Save £250 Per Person Book Now
4 Nov 2019 CUWHW - Cuba - Without Flights 14 £3,249.00 £3,248.00 Holiday Guaranteed to run - book now - few places left Book Now

Prices are per person

Price includes

  • 14 nights’ accommodation in en-suite rooms
  • Full board from dinner on arrival to breakfast on departure, less one lunch and one dinner*
  • A full programme of guided walks led by local guides and an HF Holidays' leader
  • All sightseeing and entrance fees
  • Travel by private, air-conditioned coach/minivan 
  • Tips
*Except April departure, owing to flight times

Other important information

  • Single room: £499
  • Non-member associate fee: £10 per person

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