Cuba on Wheels: Cycling Tour from Havana to Trinidad

When your flight lands at Jose Marti International Airport in Havana, your pulse is already racing. The excitement of venturing to such a unique city is almost unfathomable. Havana is a city of music and vintage American cars, a mixture of glistening and crumbling colonial mansions, and filled with elegant plazas. Your private transfer greets you at baggage claim and escorts you to the heart of the Old City. Cars with 1950s Cadillac frames and bright pink Chevrolet designs cast an image of a city set in the past. The stone façade of Castillo de San Salvador de la Punta watches over the edges of the sea.

The fortress provided a strategic position in the maritime defense of the city beginning in the late 16th century. A brass and wood chain connected the stronghold to Castillo de los Tres Reyes del Morro. In the case of a naval attack, the chain was tautened, which prevented ships from entering the harbor. A grand statue of General Maximo Gomes stands at the center of a traffic island. The war hero fought for Cuban independence from Spain in the 19th century. The general sits atop a horse and watches over the western edge of the old city, combining bronze and marble work that creates an enchanting impression.

When the sun rises over the city the circling beam from the lighthouse fades. Various shades of blue cast across the water return to frame Havana. Waves splash against the sea walls of the Malecón. The aroma of salt water fills the air. After breakfast, your guide helps fit you to a perfect bicycle to ensure comfort and ease during your tour. Once you find the proper shoes and bike, you set out to discover the eclectic charms of the city. Old men play dominoes on foldable tables outside dilapidated buildings. Painters set their canvases along the bright walkway lining the center of Paseo del Prado, finding shade and inspiration beneath the lining trees.

Musicians play music and dance inside the restaurants of Old Havana, filling the entire neighborhood with endless energetic music. The aroma of fresh coconut follows you along the avenues. The former Presidential Palace now houses the Museum of the Revolution. President Menocal inaugurated the palace in 1920. The neoclassical architecture stands out from the art deco and colonial styles of the old city center. Tiffany’s of New York decorated the interior with dazzling elegance. The Salon de los Espejos, the Room of Mirrors, has a similar design to the room of the same name at Versailles, utilizing space, light, and reflection to captivate visitors. The opulence of the building contrasts the socialist era exhibits.

In the morning, you wake up in the charming town of Matanzas, which the Spanish settled in the 17th century. The literary and musical heritage beginning in the 18th century gave the city the nickname “Athens of Cuba.” The ambiance of the city retains a cheerful, undefeated quality emanating from the revitalized central plaza. A book publisher in Plaza de la Vigia produces handmade paper and first-edition books that are also typed, stenciled, and pasted together by hand. After breakfast, your guide leads you out of the city on a journey to Playa Larga, encompassing approximately 56 miles.

Once outside of Matanzas, the aroma of citrus fills the air, radiating from the vibrant orchards. A narrow, single road winds through the countryside of what used to be sugar cane fields for as far as the eye could see. You share the road with antique Soviet-era tractors and vintage American cars. You pass the occasional horse hauling a small buggy filled with crops, driving by a local farmer. You stop in the town of Triumvirato, home to a historic sugar mill where Carlota’s Rebellion took place.

A monument dedicated to the uprising and the leader, Carlotta, rises out of the lush grass. Carlotta stands at the center of the stone, tall and powerful. In the 1840s, armed with only a machete and strength of will, she led the slaves working the plantation in rebellion. The monument is a reminder of Cuba’s tumultuous relationship with slavery. Once at Playa Larga, you can relax on the coastline. The waves crash against the powder white beach, offering a soothing sound and refreshing breeze to cool you down.

At dawn, the wildlife around Playa Larga comes to life. Cuban Trogons perch on moist forest branches. Their blue crown and red belly stand out from the emerald leaves. Bee hummingbirds, the world’s smallest bird, which is found only in Cuba, flutter around blossoming flowers. They can grow to over two inches in length and radiate color from iridescent plumage around their throat and beak. Take the time to visit the Bay of Pigs Museum before beginning your ride to Cienfuegos. Playa Larga was one of three beaches American troops landed on during the 1961 invasion.

Exhibits commemorate the Cuban troops that fought during the altercation, along with stories of the two-country encounter. Five M41 Bulldogs are on display outside of the museum setting a unique scene. Once settled on your bike, you make the 28-mile trek to Cienfuegos, Cuba’s city by the bay. The French founded Cienfuegos in the 19th century. Pearl-white buildings rise above the gridded streets leading to the water. An 18th-century fortress known as Nuestra Senora de los Angeles de Jagua continues to protect the bay from invaders. Over the years, the city has combined French elegance with a Caribbean spirit. Enjoy an elaborate meal on the waterfront overlooking the immaculate panorama of the city set against the sea.

The morning light glints off of the pearled facades. The red-tiled dome of the Palacio de Gobierno contains a fiery glow above the Plaza de Armas. Today you travel around 50 miles from Cienfuegos to the fascinating colonial town of Trinidad, which holds the spirit of Cuba. Climb the steep hills outside of town to view the rolling peaks of the Escambray Mountains in the distance. Emerald sugarcane fields sweep across the valley. Reach the coastline after mile 31. The final stretch of your journey travels alongside the glistening water. The textured mountains rise out of the water in the distance.

The road hugs the meandering cliff before the rugged rocks descend into the sea. The salty aroma and refreshing breeze urge you forward. The layers of turquoise and cobalt blue reach the horizon. You pass grazing cows and the occasional classic car. White sand beaches edge the shore the closer you come to Trinidad. The city was founded in the 16th century and remains the best-preserved colonial town in Cuba. The surrounding plantations once grew tobacco, sugar, and even coffee. This evening, you can enjoy a home cooked meal at a casa particular, a welcoming bed and breakfast, inside the heart of the atmospheric city.

Trinidad combines the beauty of the beach with the elegance of the undulating mountaintops, both bordering the city’s cobblestones streets. Horses clop through town hauling crops and transferring locals. Pastel homes accentuate the already spirited ambiance of the city. You can hear the sounds of salsa emanating from cafes. The aroma of rum and pineapple drift out of lively bars. The day is yours to experience Trinidad as you desire, from enjoying a cultural walking tour to erupting with rhythmic energy during a private dance class. For a unique view of the countryside, you can enjoy a steam train trip to Valley of the Sugar Mills.

The antique train retains its classic allure. The tracks lead into the Agabama Valley, a UNESCO protected area. Once the train ascends into the vale, you can see the powerful Hacienda Iznaga, a 144-foot tall tower allocated to watching slaves. Pedro Iznaga founded the estate in the late 18th century and later became one of wealthiest men in Cuba. You can climb to the top of the tower for a pristine panorama of the valley. The peach glow of the opulent mansion stands out from the greenery and sporadic ruins of the once glamorous sugarcane industry.

Small fishing boats set sail from the nearby marina. Fishermen cast their nets onto the water in search of fresh, feisty fish to bring back to the town of Trinidad. You wake up early and set out on the exciting road to Santa Clara. Follow the path of Cuba’s pro cycling racers during the “Vuelta de Cuba,” traipsing up the steep hills through Topes de Collantes National Park. The switchback roads twist and turn across the foothills. The aroma of pine and eucalyptus are refreshing. At the summit, you can hear the tropical birds chirping beneath the canopy. In the distance, Caburni waterfall cascades into an iridescent pool of freshwater.

The park encompasses more than 77 square miles of crenulated mountaintops, meandering vines, and dense forest. The pine trees change to palm trees. The aroma of eucalyptus fades beneath the sweet scent of fresh coconut. By the time you reach Santa Clara, you have traveled approximately 52 miles along the undulating country road. Before checking in to your hotel, your guide leads you to the magnificent Che Guevara Memorial adorned with a 22-foot tall statue of the guerilla leader guarding the large plaza. A relief depicts Che in the Sierra Maestra Mountains speaking with Fidel Castro. Che looks into the city, inspiring the spirit of revolution that continues to galvanize the local student population.

In the morning, local workers make their way to Santa Clara’s tobacco factory, Fabrica de Tabacos Constantino Peres Carrodegua. The factory produces some of the most notable cigars in the country, including Montecristo and Romeo y Julieta. The aroma of freshly brewed coffee drifts out of the café across the street from the factory. Today, you return your trusted bicycle to Havana, boarding a private transfer for your scenic drive back to the bustling city. The sounds of the crashing waves along the Malecón are familiar.

The outline of the Castillo de Lost Tres Reyes del Morro is a welcomed sight along the bay. Today you get to experience a different side of the city; step into a Classic refurbished American car for a vintage tour of Old Havana. The sleek body runs from bulbous headlights to rear wings. The two-tone pink and white paint accentuate the white leather interior. The antique image of the city surrounds the seasoned vehicle. Women in bright clothing puff on over-sized cigars.

Cruise down the Paseo del Prado, which connects to the Malecón. A tall statue of Jose Marti recalls the hero’s struggle for Cuban independence from Spain. Bronze lions frame the walkway at the center of the street. Musicians play elaborate songs, and artists capture the daily life of the old streets. In the evening, you celebrate the end of your journey at La Floridita, Ernest Hemingway’s favorite restaurant. Order one of El Floridita’s famous daiquiris, and commemorate a toast to the journey of the past and the adventures to come.

The highlights of Old Havana continue to beckon to you during your final morning in Havana. Guitarists already roam the cobblestone streets searching for inspiration in the quiet hours of the day. The Hotel Nacional de Cuba stands atop a former bunker providing spectacular views of the surrounding city leading out to the sea. The grounds acted as Fidel Castro’s headquarters during the Cuban Missile Crises. The wealth of natural beauty and captivating culture is endless on the island. Your private transfer meets you at the hotel and escorts you to Jose Marti International Airport. When the plane takes off, you know that soon you will return for another unique cycling tour of Cuba.