After breakfast we head to the Cubania workshop to meet the team and fit your bike then, after a safety briefing, we set off on a warm up ride exploring the best of Cuba’s capital city. We catch glimpses of the sea as we cycle through the leafy 1950s Miramar district, home to some of Havana’s most striking 20th Century architecture. Keep an eye out for the imposing Russian embassy and the elegant neoclassical homes, many of which are now embassies.

We dip into the emerald green Havana metropolitan forest and emerge close to Revolution Square, the hub of the Castro Regime, where we stop for photos. From here it’s an easy ride to Old Havana, passing through the cultural district of Vedado and bustling Centro Habana before reaching Capitolio building, Cuba’s mirror-image of Washington DC’s Capitol Building. With the Capitolio behind us we veer left down the regal Prado promenade, a favourite with street artists and skateboarders alike.

We finish the city cycle in the Old Town next to the Bay of Havana. Lunch will be a quick packed lunch before our 4 hour bus transfer to Cienfuegos. After checking into our casas particulares we have the remainder of the afternoon and evening free to explore the attractive coastal city of Cienfuegos. Cuba’s ‘Pearl of the South’ was home to Cuba’s bolero star Benny Moré, and is renowned for its stylish French architecture and its malecón, a seawall that skirts the city’s bay.

Today’s rides is a scintillating mix of nippy hills and rolling countryside as we leave coastal Cienfuegos and skirt round the Escambray Mountain range passing rural towns, fields of sugar cane and crossing rivers and sparkling Caribbean inlets.

We leave Cienfuegos taking an undulating road past mango groves before climbing some short, sharp, hills through pasture lands. After approximately 20 km we stop to enjoy stunning views of the Escambray mountains across a sweeping valley of sugar cane. The road then dips and rolls over gentle hills until we stop for lunch at La Vega farm restaurant. From here the road clings to the Caribbean all the way to Trinidad.

Trinidad is one of Cuba’s finest colonial cities and we’ll dedicate plenty of time to exploring it towards the end of our ride. Today, we stop riding in Trinidad’s outskirts and transfer approx. 1 hour so that we can spend the night in the charming but less known colonial town of Sancti Spiritus.

Sancti Spiritus is a provincial capital and one of the first seven villages founded by the Spanish Conquistadors in the early 16th century. This is a quiet, parochial place steeped in history. Its inhabitants are proud of the Iglesia Parroquial Mayor del Espiritu Santo; the oldest operational church on the island, as well as Puente Yayabo, the only European-style redbrick bridge in Cuba.

Cuba is big! So, rather than spend many days cycling across the flat plains of Central Cuba, we take a long travel day by bus and fast forward to the eastern province of Holguin.

The journey time should be approx. 7 hours depending on the road conditions and it’s a good time to ask your guide all those burning questions on Cuban history , culture and everyday life. We’ll reach the provincial town of Holguin in the afternoon.

Many people consider Oriente, or the Eastern Provinces, to be the most authentically Cuban part of the island. The roots of Cuban music and much of its Afro-Caribbean culture can be traced to the area and it was in Santiago de Cuba that Fidel Castro and his fellow revolutionaries began their uprising against the dictator Batista.

After breakfast we set off by bus to our start point at Cueto, a short distance from Holguin. We go deep into the Cuban countryside and take the undulating road immortalized in one of Cuba’s best-loved songs “Chan Chan”, the song which opens Wim Wenders’ Oscar winning “Buena Vista Social Club”. Sharing the road with cyclists, horses and carts and classic American cars through quaint villages and agricultural land dotted with royal palms, it’s hard not to imagine you’ve time travelled back a hundred years to a gentler, rural way of living. After a picnic lunch along the way, we load our bikes at Moa and drive onwards along the spectacular (but poor road surface) route towards Baracoa.

If time allows, we’ll stop for a quick dip in the sea in Maguana before reaching Baracoa.

Founded in 1512, Baracoa was the first Spanish settlement, discovered in 1492 by Christopher Columbus on his 1st trip to the West Indies. The area is lusciously fertile and mountainous with gushing rivers flow into Baracoa’s sandy bays. Closed off to the rest of the island by a mountain range, its isolated location on the easternmost tip of the island left it open to attacks from pirates, smugglers ( also known as the English ) so three forts were constructed in the 18th Century for protection.

Baracoa was finally connected to the rest of Cuba in the 1960’s when La Farola road was engineered with tunnels through the mountains and viaducts soaring over valleys. This area is renowned for coconuts, cocoa and chocolate production. The Malecón on the northeast side of the town is known as the Caribbean’s first ocean drive. There is still a strong indigenous influence here and the El Yunque Mountain, (the anvil shaped mountain described by Christopher Columbus in his diaries) was the site of various aboriginal communities. We arrive late afternoon and enjoy a free evening to explore the town after checking into our accommodation.

Today we’ll have a day off the bike to explore Baracoa. The idyllic tropical landscapes more than live up to Christopher Columbus’ claim Cuba was “the most beautiful land ever seen by human eyes”. The relic of the cross he planted into Cuban sand upon landing can still be seen in Baracoa’s Cathedral and the town is still a sleepy backwater of fishermen and farmers who lived in isolation for centuries before the

town was connected to the rest of Cuba by La Farola, the mountain road to Guantanamo city.

You’ll find culinary influences from Haiti just across the water and culture is rooted to the indigenous ways of the Taino and Arawak people who once thrived in Cuba.

Our guide will explain all possible activity options and how to book excursions should you wish to go on a trek in one of the nearby national parks.

After an easy day in Baracoa, we prepare this morning for one of the most iconic climbs in Cuba. La Farola road takes us from Baracoa up and over the mountain range and drops down to the Southern coastline near Imias. This is a challenging ride rewarded by spectacular vistas as you climb up into the hills and through the tunnels which were engineered in the 1960s to connect remote Baracoa by road to the rest of Cuba.

Cuba’s Tour de France equivalent, the Vuelta de Cuba, traditionally held in February has always included this climb in one of the étapes.

Some may decide to end their day’s ride at Imias with a picnic lunch and a dip in the sea. The rest will continue cycling into Guantánamo province, equally famous for its US Naval Base and for the Cuban song Guantanamera, a love song to Cuba.

We reach the provincial capital of Guantánamo and transfer from here to Santiago, Cuba’s second city and former capital during colonial times.

Santiago de Cuba is known as the ‘city of heroes’ owing to the important role it played in Independence and Revolutionary struggles. Santiago rivals Havana in literature, music and politics, has rich cultural traditions and is considered by all to be the birthplace of Cuban music. It was here that Fidel Castro was educated as a schoolboy and his remains were returned to Santiago where he is buried in the Santa Ifigenia Cemetery, close to Cuba’s National Hero and Poet José Martí.

After checking into your casa particular, enjoy an evening of music and mojitos on the streets of Santiago.

Leaving the hustle and bustle of Santiago we climb West out of the city and take the pretty Santiago to El Cobre road through the foothills of the Sierra Maestra.

We stop for a short visit to the Basilica of Nuestra Señora del Cobre, Cuba’s most important religious shrine and a site of pilgrimage for Cubans who pay homage to Cuba’s patron Saint. We continue into the foothills, stopping in Contramaestre for a picnic lunch and a cold drink before continuing along the relatively flat road to Bayamo.

Bayamo is one of the 7 original colonial “villas” founded by the Spanish Conquistadors. We visit the town centre and learn about its importance in kickstarting Cuban Independence. Even today Cuba’s National Anthem is named after this provincial capital.

Continue by bus high up into the Sierra Maestra mountains where we stay the night in Villa Santo Domingo.

We spend this morning in the Gran Parque Nacional Sierra Maestra, a spectacular national park within Cuba’s highest mountain range.

This region is well known as Fidel Castro’s base of operations during the Cuban Revolutionary War. High in the Sierra is Comandancia La Plata, the secret mountain hideout from which Castro and Che Guevara planned the revolutionary war in the 1950s. It was also the location for Radio Rebelde which broadcast information for the revolutionaries. We will hike up to the revolutionary base through the lush vegetation.

After time for lunch in Villa Santo Domingo, we continue our journey to Camagüey, a World Heritage Site, where we’ll spend the night. After almost continuous attacks from pirates, the original city (founded as Santa Maria del Puerto del Principe around 1515 on the northern coast) was moved inland in 1528. The new city was built with a confusing layout of winding alleys that made it easier to defend from raiders.

Today we cross the flat plains of Cuba leaving the Oriente behind and heading back into Central Cuba.

We set off early in the morning to make the most of the cooler morning hours and hit the Carretera Central all the way to Majagua. The route is flat and fast and takes us through small towns and pasture land and we share the road with a variety of local vehicles, from bicycles and horses and carts to tractors and Russian lorries! There are few undulations along the way, and we stop for a packed lunch in a shady spot. Our ride finishes at Majagua where we climb onto the bus and transfer about 2 hours to our destination.

Tonight we stay high up on the banks of Hanabanilla Lake in the Escambray Mountains. The beautiful surroundings were once exclusively enjoyed by Cuban political leaders who would come to relax and fish on the reservoir. Nowadays the simple hotel welcomes visitors who choose the area for the stunning views of the lake and surrounding tropical mountains.

Today’s ride is one of the prettiest as we backtrack down the hill towards Manicaragua before heading to Guinia de Miranda, a small village in the mountains which is well known to Cubans for being the location of one of the crucial Revolutionary battles against the dictator Batista. You’ll pass commemorations of the battle and images of Che Guevara who led the attack on the Army Barracks.

The terrain today is hilly but the road surface is relatively smooth and there’s hardly any traffic as it undulates through tropical mountains, past tobacco fields and small holdings and crosses rivers. Royal Palm trees abound and endemic birds provide a soundtrack as you ride through the hilltops.

After Rio Seibabo we start dropping down towards Condado and we finally reach the main road at Manaca Iznaga. Located in the Valley of Sugar Mills, the ruins of the Manacas bell tower remind us that this area of Cuba was once covered in sugar cane and the plantation provided enormous wealth to colonial masters and immense suffering to their slaves. It’s a fitting introduction to Trinidad, 15km away, which became enormously wealth through sugar cane production and explains why this small town is packed with beautiful colonial buildings.

Today is free for you to explore Trinidad at your own pace.

Trinidad is probably Cuba’s most famous provincial town and rightly so. It has been a UNESCO World Heritage Site since 1988 and is perhaps the best-preserved colonial town on the island. Exploring Trinidad is like stepping back in time; the pastel coloured houses, cobbled streets and horse drawn transportation whisk you back to colonial times.

There are a number of interesting museums housed in old colonial buildings to visit during the day, or you may wish to cycle to the nearby beach at Playa Ancón, which is an approx. 25km round trip from Trinidad. As the sun sets that Trinidad really comes alive with music and dance. Ask your guide for tips and advice, or for help booking any activities.

Following the Vuelta de Cuba, we are challenged with the Topes de Collante climb this morning. Setting off from Trinidad warm up for 5km before we turn towards the mountains and start to climb immediately. Although shorter than the climb out of Baracoa, the climb to Topes is no less intense, gaining 800m in approximately 12km. The road twists and turns past palm trees, bamboo forests and into the pine forests, a challenging climb with unforgettable views back across the hills to the Caribbean Sea.

Reaching the summit, we take the road less travelled towards Cienfuegos undulating out of the pine forested peaks in Topes and down into tropical forests as we descend. Once out of the mountains we take the main Trinidad-Cienfuegos road with nippy hills through pasture land and wide vistas of the Caribbean sea and the bay of Cienfuegos.

We finish our ride in the main square at Cienfuegos and, after a cold beer and time to explore the surroundings, we head to our accommodation for the night on the Bay of Pigs. Our casa for tonight is located on the beach at Playa Larga, a great spot for a swim and dinner on the beach.

Yesterday was a challenging ride, today you have the chance to warm down and stretch muscles with a flattish final day of riding.

This morning we pedal inland through the Ciénaga de Zapata National Park, a vast marshland home to Cuba’s most important bird species and world-renowned as a UNESCO Biosphere Reserve. Playa Larga was one of the most important battles sites of the attempted invasion of Cuba by US backed militia in 1961. You’ll see monuments to the fallen along the road as well as propaganda posters reminding visitors of the area’s history.

Leaving the park we pass through Australia village with its old sugar mill before cycling through citrus plantations and the small town of Pedro Betancourt (named after a revolutionary major-general in the Cuban war of independence).

Our destination is Matanzas known as the “City of Bridges” or the “Venice of Cuba” as its streets span three different rivers. It is also the birthplace of two Cuban dances; rumba and danzón, as well as several religions of African origin, making it a vital contributor to Afro-Cuban culture. We finish our ride on one of Matanzas’ main squares and enjoy the views with a mojito or a cold beer in hand.

From Matanzas we will transfer back to Havana for the night (approximately 2 hours).

After breakfast your guide will take you on a walking tour of Old Havana which is the finest surviving Spanish colonial city in the Americas. Since it was declared a UNESCO World Heritage Site millions of dollars have been invested in its restoration. The many marvellous monuments, cathedrals and palaces of the city’s historical centre are brought to life by a constant hustle and bustle and the unmistakable sound of Cuban Son.

We’ll have lunch at a paladar in the Old Town and then you will have some free time before your transfer to the airport. We will then say Adiós, or, as we prefer to say hasta luego, see you later!

Afternoon transfer (30–40 minutes approx.) to Havana airport.