Highlights of Cuba

Vintage classic american car in Havana, Cuba
Duration: 14 nights
Type: Worldwide walking holidays
Walking Grade: 2

From the vibrant and salsa-loving capital of Havana to the tobacco fields and rainforest of the Viñales Valley, Cuba packs in a glorious variety of natural wonders and cultural thrills. Highlights include following in the footsteps of Ernest Hemingway, learning how to roll a tobacco criollo, exploring the Caribbean coast in the Northern Cays, and discovering the historic heart of Trinidad – the UNESCO-listed city famed for its incredible architecture and laid-back Cuban vibe.

What you’ll love

  • Taking a walking tour of Habana Vieja (Old Havana)
  • Walking among the tobacco fields of Viňales
  • Learning how to roll the perfect cigar
  • Debating the legacy of Che Guevara
  • Staying in in a casa particular (private home)
  • Cocktails at El Floridita, Hemingway’s favourite bar

What’s included

  • Return flights from London Gatwick including baggage and transfers
  • Guided walks and sightseeing with local leaders
  • 14 nights’ touring accommodation across Cuba
  • 14 breakfasts, 14 lunches & 14 dinners
  • All sightseeing and entrance fees (as per itinerary)
  • A walking tour of Old Havana
  • All in-destination transport

Trip Notes

Easy to download as a PDF, our trip notes provide detailed information for every holiday. Please click below to find the trip notes for your departure date.

All our carefully-curated itineraries are designed by our experts. While we make every effort to adhere to the described itinerary, we may take alternative routes or adapt the running order for weather and/or operational reasons.

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.

Hotel Nacional de Cuba, Havana - Cuba

Located on Havana’s stunning seafront promenade, the Malecon, the historic Hotel Nacional de Cuba is a true icon of the city. Once a hangout for famous stars like Frank Sinatra and Ava Gardner, powerful heads of state, and American mob bosses, it’s now a UNESCO-listed National Monument. A symbol of Cuban identity, this imposing hotel offers commanding views of the sea and the city from Taganana Hill. Featuring eclectic 1930s architecture, the Nacional boasts 457 rooms, three restaurants, a café, four bars, and a snack bar. Enjoy a drink in the Hall of Fame bar, where you can spot photos of the famous faces that have visited over the years. Or, catch the “Habana de Fiesta” show at the famous Parisien Cabaret to discover Cuba’s history through vibrant music and dance


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 features unique Baroque neoclassical architecture. 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.

Hotel Nacional de Cuba, Havana - Cuba

Located on Havana’s stunning seafront promenade, the Malecon, the historic Hotel Nacional de Cuba is a true icon of the city. Once a hangout for famous stars like Frank Sinatra and Ava Gardner, powerful heads of state, and American mob bosses, it’s now a UNESCO-listed National Monument. A symbol of Cuban identity, this imposing hotel offers commanding views of the sea and the city from Taganana Hill. Featuring eclectic 1930s architecture, the Nacional boasts 457 rooms, three restaurants, a café, four bars, and a snack bar. Enjoy a drink in the Hall of Fame bar, where you can spot photos of the famous faces that have visited over the years. Or, catch the “Habana de Fiesta” show at the famous Parisien Cabaret to discover Cuba’s history through vibrant music and dance


Driving 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.

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.


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.

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.


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.

Hotel Los Caneyes - Cuba

Less than two miles from the Che Guevara memorial, this hotel offers a great location for a one-night stay. The hotel benefits from an outdoor swimming pool, restaurant, snack bar and small shop. Dotted around the hotel’s large gardens, the rooms are cabana style and come with ensuite facilities, air conditioning and a television.


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.

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.


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.

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.


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).

Casa particulares Alberto y Osmary - Cuba

A popular casa in a central, quiet location, Casa Osmary and Alberto is ideal for small groups. Rooms are simply furnished but comfortable, each with its own theme, all with air conditioning and ensuite facilities.


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 built by a Sugar Baron, to keep an eye on his staff working in the Sugar Plantations.  

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 has been a UNESCO world heritage site since 1988, because of its historical importance, as it 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.

Casa particulares Alberto y Osmary - Cuba

A popular casa in a central, quiet location, Casa Osmary and Alberto is ideal for small groups. Rooms are simply furnished but comfortable, each with its own theme, all with air conditioning and ensuite facilities.


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.

Casa particulares Alberto y Osmary - Cuba

A popular casa in a central, quiet location, Casa Osmary and Alberto is ideal for small groups. Rooms are simply furnished but comfortable, each with its own theme, all with air conditioning and ensuite facilities.


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.

Casa particulares Don Pepe - Cuba

Putting you in the heart of vibrant Cienfuegos, this casa is a true Cuban experience. Each room enjoys ensuite facilities and air conditioning.


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 of 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.

Casa particulares Don Pepe - Cuba

Putting you in the heart of vibrant Cienfuegos, this casa is a true Cuban experience. Each room enjoys ensuite facilities and air conditioning.


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.

Casa particulares Claxon - Cuba

Hotel Boutique Claxon is a lovingly restored casa located in the Vedado district of Havana. Each guest room is dedicated to a classic car of the 50s and offer ensuite facilities, 24-hour room service and free Wi-Fi. The hotel also has a café and bar area.


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.

Casa particulares Claxon - Cuba

Hotel Boutique Claxon is a lovingly restored casa located in the Vedado district of Havana. Each guest room is dedicated to a classic car of the 50s and offer ensuite facilities, 24-hour room service and free Wi-Fi. The hotel also has a café and bar area.


Our final morning is at leisure,. After lunch, our with-flight guests transfer to Havana airport to begin our return journey back to the UK.


With-flight guests arrive back in the UK.


Itinerary map for Cuba

Hotel Melia San Carlos - Cuba

With an enviable location in the heart of historic Cienfuegos, the Melia San Carlos puts you in easy reach of the city’s must-see sights. When you’re not busy exploring, relax in comfortable rooms that combine tradition and modernity, or enjoy the views from the Roof Garden with a cold drink or two.

Hotel Nacional de Cuba, Havana - Cuba

Located on Havana’s stunning seafront promenade, the Malecon, the historic Hotel Nacional de Cuba is a true icon of the city. Once a hangout for famous stars like Frank Sinatra and Ava Gardner, powerful heads of state, and American mob bosses, it’s now a UNESCO-listed National Monument. A symbol of Cuban identity, this imposing hotel offers commanding views of the sea and the city from Taganana Hill. Featuring eclectic 1930s architecture, the Nacional boasts 457 rooms, three restaurants, a café, four bars, and a snack bar. Enjoy a drink in the Hall of Fame bar, where you can spot photos of the famous faces that have visited over the years. Or, catch the “Habana de Fiesta” show at the famous Parisien Cabaret to discover Cuba’s history through vibrant music and dance

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 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.

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.

Hotel Los Caneyes - Cuba

Less than two miles from the Che Guevara memorial, this hotel offers a great location for a one-night stay. The hotel benefits from an outdoor swimming pool, restaurant, snack bar and small shop. Dotted around the hotel’s large gardens, the rooms are cabana style and come with ensuite facilities, air conditioning and a television.

Casa particulares Alberto y Osmary - Cuba

A popular casa in a central, quiet location, Casa Osmary and Alberto is ideal for small groups. Rooms are simply furnished but comfortable, each with its own theme, all with air conditioning and ensuite facilities.

Casa particulares Don Pepe - Cuba

Putting you in the heart of vibrant Cienfuegos, this casa is a true Cuban experience. Each room enjoys ensuite facilities and air conditioning.

Casa particulares Claxon - Cuba

Hotel Boutique Claxon is a lovingly restored casa located in the Vedado district of Havana. Each guest room is dedicated to a classic car of the 50s and offer ensuite facilities, 24-hour room service and free Wi-Fi. The hotel also has a café and bar area.

Essential information

It's best to be prepared for all weather conditions. To make it easier, here is a list of items you should consider packing.   

Essentials  

  • Walking boots 
  • Waterproof jacket 
  • Waterproof trousers 
  • Insulated jacket/top 
  • Walking clothing  
  • Walking socks (plus spares)  
  • Sunhat 
  • Gloves/mitts and warm hat
  • Water bottle (minimum 2 litre capacity)  
  • Headtorch 
  • High-factor sunscreen (minimum SPF 30)  
  • Sunglasses with a dark lens 
  • Rucksack (15-30 litres)  
  • Mobile phone 
  • Personal first aid kit (containing your medication, blister plasters, etc.) 
  • Passport 
  • Visa (if applicable) 
  • Copy of your travel insurance policy 
  • UK Global Health Insurance Card (formerly known as EHIC

Recommended

  • Collapsible walking poles 
  • Swimwear and travel towel
  • Snacks
  • Dry bags
  • Rubbish bags
  • Insect repellent

Optional extras

  • Camera 
  • Sit mat
  • Flask for hot drinks 
  • Durable lunch box
  • Gaiters 
  • GPS device 

Guest reviews

All holidays are subject to availability. Supplements may apply.

Non-member fee: £30 per person.

If you choose land only, you will be responsible for making your own travel arrangements, including your flights and airport transfers at your destination. Any flights booked independently will also not be covered by our ATOL license.

Date (Start - End) Itinerary Double / Twin Room Single Room Notes / Offers Trip Notes Book
2025

19 Jan - 03 Feb 2025

14 nights

Itinerary (2025)
Flight from London Heathrow Airport

Single Call to Enquire
Double Call to Enquire
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Date (Start - End) Itinerary Double / Twin Room Single Room Notes / Offers Trip Notes Book
2025

19 Jan - 03 Feb 2025

14 nights

Itinerary (2025)

Single Call to Enquire
Double Call to Enquire
Call to Enquire Call to Enquire Trip Notes

Important information

  • With flight holidays: Price includes return flights to Havanna, hold baggage and airport transfers

*If you prefer to make your own travel arrangements, please ensure you’ve selected a land-only option before proceeding to book.

Duration:
14 nights
Type:
Worldwide walking holidays
Walking Grade:
2

Call to Enquire

020 3974 8865

For group bookings of 10+ guests click here

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Carbon Footprint 3147Kg of CO₂e

Average carbon footprint per person Learn More