Highlights of Cuba

Cuba Guided Walking Holiday

Vintage classic american car in Havana, Cuba
Duration: 14 nights
Type: Worldwide Multi-Centre
Walking Grade: 2
from £2,929pp without flights FLIGHTS AVAILABLE

Explore this colourful Caribbean island with a fascinating history. 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 variety of landscapes ripe for exploration.

Holiday Highlights

  • Take a walking tour of historic Habana Vieja and explore the city in a classic car
  • 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

What’s included

  • A full programme of guided walks and sightseeing led by Local Guides
  • 'With flight' holidays include return flights from the UK and hotel transfers
  • Full Board with en-suite accommodation - 14 breakfasts, 13 lunches, 13 evening meals
  • All entrance fees
  • All walks transport and tips

Trip Notes

Trip notes are detailed, downloadable PDFs for each holiday.

Download Trip Notes

On our Worldwide holidays, our day-by-day descriptions will help you understand where you’ll be exploring and what you’ll be doing. The itineraries are put together carefully to give you the best experience. While every effort will be made to adhere to the described itinerary, we may occasionally vary the sequence shown here or substitute an alternative to suit local conditions or for other operational reasons. In the wake of disruption caused by the Coronavirus outbreak to planning, this is particularly relevant to itineraries in 2022.

On arrival in Havana you’ll meet your local guide and driver who, depending on your arrival time, will take you to your hotel for a welcome drink and, later, a typical Cuban dinner at La Barraca in the gardens of the Hotel Nacional. You will stay at either the Hotel Nacional de Cuba or the Hotel Capri.

We take a walking tour to the historic heart of Havana. Granted UNESCO World Heritage status in 1982, the old town, or ‘Habana Vieja’, has been handsomely restored and is the largest colonial centre in Latin America. Our tour will take in many of Havana’s sights, including a visit to Plaza de Cathedral, Plaza Vieja and the old City Walls. Lunch will be in a local paladar restaurant.

The day will also include a visit to the Finca Vigia, Ernest Hemingway’s home in Cuba and now lovingly kept as it was when he lived there, and a visit to the Hotel Ambos Mundos where the author lived for more than two years.

We’ll also ride out by bus to Cojimar, where Hemingway moored his boat ‘El Pilar’, and enjoy a refreshing drink at one of his favourite restaurants, ‘Las Terrazas’, which overlooks the ocean. The fishing village is full of memories of the great American novelist and he kept a home close by for more than 20 years. We round off the day with a tapas dinner and cocktail making class.

Distance – approx 210km

We drive west, past plantations and cultivated fields, to the beautiful Viñales Valley. We’ll enjoy lunch and a cigar rolling demonstration at a typical Cuban farm.

Our afternoon walk along the Palmarito trail takes in the spectacular scenery of the valley, with its limestone mogotes and their sheer cliffs. This is a traditional farming area and we stop at a small community to see how they cultivate tobacco, root vegetables and coffee. Distance: 4 miles (6½km), no ascent.

In the evening, a further walk along the Sendero Valle del Silencio in this enchanting countryside will prepare your appetite for dinner at Wilfredo’s Organic Farm. Set in a beautiful hilltop location overlooking the town we will hopefully witness a marvellous sunset as we enjoy our meal. Distance: approx. 2 miles (3km), no ascent.

Today we start early and with a packed breakfast to walk along the Acuaticos trail, heading up into the hills around Viñales for sunrise. Distance: approx. 5 miles (8km) with 800 feet (243m) of ascent.

We continue into the heart of Cuban tobacco country and drive through the provincial capital, Pinar del Rio, to visit a tobacco factory where famous cigars are hand-rolled according to traditional methods. We head to the ‘vega’ of a famous Cuban tobacco producer, where we visit the farm and learn about the subtle art of producing fine tobacco. We’ll have lunch at the ‘vega’ before returning to Viñales, where the rest of the day is at leisure before dinner at a local paladar.

Today is mostly a travel day (approx. 6 hours over approx. 500km) as we head towards central Cuba. We’ll visit Las Terrazas Biosphere Reserve to learn about the reforestation programme started in the 1970s and take a short trail, La Serafina, in the hopes of spotting local birdlife. Distance: approx. 4 miles (6km).

After lunch on an old coffee plantation, we continue to Santa Clara. If time allows today, we’ll visit the Che Guevara memorial, resting place for Che and sixteen of his men who were killed in action in 1967 in Bolivia, and have dinner at the hotel.

If we didn’t have time to visit the Che Guevara memorial, we’ll do this today before departing for the city of Remedios, located about an hour to the northwest of Santa Clara.

Well off the beaten path and forgotten by most tour operators, Remedios is one of the oldest towns in Cuba – now a National Monument town – and the 17th century colonial architecture dominates this peaceful town. We’ll take in the city and its historic centre on a relaxed tour. The key attraction is the main square with its colonial church, ‘Iglesia Mayor’ of San Juan Bautista, which possesses thirteen beautifully decorated gold altars.

We continue to the beautiful Northern Cays of Cuba and our all-inclusive hotel, where we’ll have lunch and the remainder of the day is at your leisure.

Today, take some time to relax in the resort. Enjoy the hotel’s facilities or explore the nearby area – perhaps a swim in the sea or a short walk along the white sand beaches or through the nearby tropical woodland.

Driving distance – approx. 180 km in total.

After breakfast we travel to the Escambray Mountains, where we’ll walk along the banks of the Hanabanilla Reservoir, along the Guanayara Trail, and through coffee and fruit plantations. This is the least accessible – we travel to the start of the walk by truck – but by far the most rewarding hike from Topes de Collantes, and there is a steep descent to the El Rocio waterfall.

We’ll arrive at La Gallega ranch, a traditional rural hacienda, in time for a simple country lunch before we continue our journey to Trinidad and our accommodation. This evening we’ll have dinner at Alberto’s House and enjoy an authentic Cuban experience. Distance: 3 miles (5km).

Today we travel out of Trinidad to visit the Valley of the Sugar Mills (‘Valle de los Ingenios’). This fertile plain, with the Sierra del Escambay in the distance, is carpeted in the green hues of sugar cane. The valley is dotted with ruins of 19th century sugar mills.

We visit the Manaca Iznaga estate where we can wander through the ruins and climb the seven-storey tower for wonderful views. The tower was once a lookout for supervising the slaves. The estate is a telling reminder of the days of colonisation.

We also take a walking tour of the historic heart of Trinidad and enjoy lunch at a local restaurant. Founded in 1514 by Diego Velazquez, Trinidad is one of the most stunning colonial towns in the Americas. The city was once the centre for the sugar trade and its cobbled streets and lovely architecture bear witness to its former glories.

Tonight, you have a free evening to explore at your own pace and enjoy dinner at a restaurant of your choice surrounded by the colourful evening atmosphere of the town.

Today is a free day. There are many options including taking a visit to Playa Ancon, joining a catamaran trip to the offshore cayes, or exploring the charming streets of Trinidad a little further. A picnic lunch is provided today, and dinner will be together as a group at a local paladar.

Driving distance approx. 90km

After breakfast we drive to the Hanabanilla Hotel and begin our walk around Hanabanilla Reservoir, this time along the La Atalaya trail. During the walk you will see typical country houses of the area, before finishing at Lago Hanabanilla from where we will be taken by boat to Rio Negro for lunch. Distance approx. 4.5 miles (7km), with some rough sections of ascent and descent.

After lunch, transfer 1½ hours to Cienfuegos Bay, and check into our hotel.

After breakfast we set off for visits to the city, Cienfuegos Botanical Garden and the Orchid Garden Macradenia, Palmira.

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. It was 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 Cuba’s most famous theatres (Teatro Terry).

We will explore the city with a sightseeing tour, including visits to the theatre and the main square before having lunch in a local restaurant. After lunch you’ll have some free time before returning to your hotel and our evening meal in a local paladar.

Driving distance approx. 260km

Today we return to Havana. We stop en route at the Zapata Swamp and in Caleta Buena; here, we can see a natural sea pool with tropical fish, enjoy a swim and have lunch.

We continue to Playa Giron, or the Bay of Pigs, the site of the final battle between Fidel Castro’s forces and the counterrevolutionary army and visit its museum to learn about the US/CIA involvement in the anti-Castro movement.

This evening we’ll enjoy a cocktail at El Floridita, one of Hemingway’s old hangouts, and round off the evening with a special lobster dinner in Old Havana.

A final day in Havana is free for independent exploration. Perhaps explore Habana Vieja further, or head out to Havana’s other main areas, Centro Habana – offering a glimpse into real-life Cuba – or the Vedado neighbourhood. You might enjoy a walk along the Malecon, Havana’s atmospheric waterfront promenade. This is a favourite gathering spot for the residents of Havana.

In the evening we enjoy a 1-hour tour in classic American cars before our last group meal in a centrally located paladar.

Our final morning is at leisure before lunch and transfer to the airport for the flight home.

Cuba Itinerary Map

Hotel Capri, Havana - Cuba

The Capri Havana is located in the heart of Havana and offers an outdoor swimming pool on the top floor with panoramic views of the city. The hotel also has a gym, sauna and Turkish bath.The air-conditioned rooms feature a flat-screen satellite TV, a safe, a seating area, a minibar, a coffee machine and a bathroom with a shower, a hairdryer and free toiletries. Wi-Fi is available for a fee. The property has 2 restaurants and 2 bars. There are also other dining options just 2 minutes' walk away. In addition, the hotel offers a massage area, a barber shop, a laundry service, medical assistance and a car rental service. 

Hotel Nacional de Cuba, Havana - Cuba

87 years of history give prestige to the classic for distinction Gran Caribe hotel chain. The Hotel Nacional de Cuba is considered a symbol of history, culture and Cuban identity. The guns that made up the old Santa Clara Battery are on exhibition at the garden, they were declared part of the World Heritage Site. The Hotel Nacional de Cuba was declared a National Monument and it was inscribed in the World Memory Register. With its privileged location in the middle of Vedado, the centre of Havana, it stands on a hill just a few metres from the sea, and offers a great view of the Havana harbour, the seawall and the city.

Los Jazmines, Viñales Valley - Cuba

Our accommodation in the beautiful Viñales Valley; its comfortable rooms and pool make it 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.

Hotel La Granjita, Santa Clara - Cuba

The 3-star Hotel La Granjita features a restaurant and bar, outdoor pool and garden. The en-suite rooms are equipped with a desk, flat-screen TV and air-conditioning. Should you need currency exchange, the hotel offers this service.

Hotel Iberostar Cayo Los Ensenachos, Cayo Santa Maria - Cuba

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, Trinidad - Cuba

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, Cienfuegos - Cuba

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

Hotel Iberostar Parque Central, Havana - Cuba

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.

Essential Information

As you’ll be carrying your own luggage at airports and between your transport and hotels we recommend you try to keep your luggage to a minimum.

These items are a general suggestion of what to pack for an active outdoor and walking holiday; depending on your destination, you may need more of some things and less – or none! – of others. You’ll know best what you prefer to wear when out walking or while taking part in other outdoor activities.

  • Walking boots (worn in), with good ankle support and spare bootlaces
  • Walking socks
  • Walking sandals
  • Lightweight fleece, waterproof trousers and jacket
  • Shorts and short-sleeved t-shirts
  • Long trousers and long-sleeved light-coloured shirts with collars to protect from the sun.

We recommend wearing walking boots on all our walks, as these provide the best ankle support and grip. Modern ‘approach shoes’ offer appropriate levels of grip and may be worn on some low-level walks, but users should be aware that they offer less ankle support. Lightweight trainers are not recommended for any walks.

Your clothing should ideally be pre-treated with insect repellent and in-built sun protection (available from specialist clothing stores such as Rohan, Cotswold Outdoor).

  • Warm fleece, scarf/buff hat and gloves
  • Torch
  • Comfortable clothes and shoes for evenings and sightseeing
  • Sun protection – sun hat, sunglasses, high factor sunscreen and lip protection
  • Water bottle – at least 2-litre capacity
  • Lightweight survival bag
  • Small/medium rucksack (30 litre) and a liner or cover to keep contents dry
  • Insect repellent
  • Personal first aid kit including: personal medication, tissues, plasters, blister kit, painkillers, antiseptic wipes, Imodium, rehydration sachets

Essential: Passport (and copies); booking confirmation; insurance cover note; HF Holidays’ registration form.

Please ensure you have access to emergency funds should you need them; carrying a credit card is probably the most convenient method.

Optional: trekking poles (especially if you find these useful); camera; umbrella; binoculars; high energy food bars; hand sanitizer gel; universal sink plug

Please note that your HF Holidays’ leader reserves the right to refuse to take any guest on a walk should they consider that a lack of suitable clothing/footwear may affect safety

Guest Reviews

All holidays are subject to availability. Prices are subject to change.
Prices based on two people sharing. Supplements may apply.
Non-member fee: £30 per person.

For 2022 departures, please note we are in the process of integrating a new booking system and you may notice some unusual pricing information displayed for a short while as we complete the work. Your patience is appreciated.

These departure dates can be booked with flights or as land only holiday options. All packages that include flights are ATOL protected. Advertised flight prices are based on UK flights departing from London. Regional departures and/or connections to London, if available, can be requested. Cabin upgrades may also be available on request.

Date (Start - End) Nights Itinerary Price Status Trip Notes Book
05 Feb - 19 Feb 2023
14 Itinerary £3,329 Trip Notes Book Now
05 Mar - 19 Mar 2023
14 Itinerary £3,329 Trip Notes Book Now
09 Apr - 23 Apr 2023
14 Itinerary £3,329 Trip Notes Book Now
29 Oct - 12 Nov 2023
14 Itinerary £3,329 Trip Notes Book Now
Date (Start - End) Nights Itinerary Price Status Trip Notes Book
05 Feb - 19 Feb 2023
14 Itinerary £2,929 Trip Notes Book Now
05 Mar - 19 Mar 2023
14 Itinerary £2,929 Trip Notes Book Now
09 Apr - 23 Apr 2023
14 Itinerary £2,929 Trip Notes Book Now
29 Oct - 12 Nov 2023
14 Itinerary £2,929 Trip Notes Book Now

Important Information

  • Single room supplement: £35 per night
14 nights
Worldwide Multi-Centre
Walking Grade:

14 nights from £2,929pp
without flights

...or call 020 3974 8865

For group bookings of 10+ people click here

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