La Sierra Maestra, Oriente Highlights

9 Days
Pdf Cuba Cycling Adventure Https://
Want to read it later?
Download this tour's PDF brochure and start your planning offline.
Almost there!
Please, enter your email address and click the button below to get itinerary sent directly to your email address.
  • 9 Days
  • Cycling Tour + one Hike
  • 6 to 20 Ppl
  • Fully Vehicle-Supported Bike Rides
  • English and Spanish
  • Available for Winter 2024
  • 16


See Cuba by Bike on this US-approved Support for the Cuban People. Bike back in time and visit Bayamo (1513) and Cuba’s first capital, Santiago de Cuba (1515). Both as culturally and historically rich today as they were centuries ago, learn why they lie at the core of the fight of Cuba’s identity. The tour also includes one of Lonely Planet’s 200 most scenic and thrilling cycling routes in the world, as well as Fidel’s Hideout in the heart of the mountain range. Check more route details on STRAVA!


View Of Cespedes Park From Casa Granda Hotel Roof Terrace

Santiago de Cuba, located on the southeastern coast of Cuba, is a city rich in history, culture, and vibrant traditions. It was Cuba’s first official capital until 1592. As the second-largest city in the country, Santiago de Cuba played a pivotal role in Cuba’s struggle for independence and has witnessed many key events in the country’s history. It holds a special place in the hearts of its residents and is often referred to as the “Cradle of the Revolution” due to its significant role in the 1959 Cuban Revolution.
The African influence is visible in the city’s music, dance, religion, and cuisine, continuing to shape the cultural fabric of the city. Santiago has a rich musical heritage, and it’s often referred to as the “Cradle of Afro-Cuban Music.” Traditional genres like son, bolero, and “trova tradicional” originated here, and the city has produced many renowned musicians and artists. Visitors can immerse themselves in the contagious music scene, enjoying live performances, impromptu street concerts, and the infectious rhythms that fill the air.

Standard Hotel


This morning after a quick bike checking, and briefing, we roll! We will enjoy a biking adventure from Santiago de Cuba to Brisas Sierra Mar and take in the beauty and tranquility of the southeastern coast of Cuba!
This will be the first segment of a ride that has already been included by the Lonely Planet as one of the Epic Rides of the World. Cuba’s Southern Rollercoaster as they call it covers some 170 km/ 106 mi, but today we do the overall easier first 66 km/ 41 mi to warm up for tomorrow. This part of the journey offers breathtaking views of the sea and the Sierra Maestra mountains. As you approach Brisas Sierra Mar, you’ll be greeted by the beautiful resort area, nestled amidst nature and offering a relaxing atmosphere.

Breakfast, Lunch, Dinner
Standard Hotel

A View One Of The Epic Bike Rides Of The World By Lonely Planet, On The Way To Marea Del Portillo, Eastern Cuba

After a good night’s sleep, we get ready for the second part of this amazing “Epic” ride. The bike route from Brisas Sierra Mar to Marea del Portillo offers a stunning and diverse scenery as we journey along the southeastern coast of Cuba. Leaving Brisas Sierra Mar, we’ll be treated to breathtaking coastal views.
The sparkling turquoise waters of the Caribbean Sea will be our constant companion, with stretches of sandy beaches and rocky cliffs. The contrast between the vibrant blue sea and the lush green vegetation along the coastline creates a picturesque backdrop for our ride.
There will be a gradual transition from the coastal plains to the majestic Sierra Maestra mountains. These mountains, Cuba’s highest mountain range, provide an impressive landscape. We’ll be surrounded by verdant hills, dense forests, and cascading waterfalls. The winding roads will take us through valleys and along mountain ridges, offering panoramic views of the rugged terrain.
As we approach Marea del Portillo, we’ll once again be greeted by the stunning coastal scenery. The area is known for its pristine beaches, with soft white sand and clear waters. We can take a refreshing swim or simply relax by the shore, enjoying the tranquil beauty of the coastline.

Breakfast, Lunch, Dinner
Standard Hotel
Day 4 :
To Niquero

Local Town Transportation Means In Niquero, Cuba

We’ll continue along the picturesque coastline, so make sure to take in the beauty of the coastal landscape, as we pedal alongside the shimmering waters.
Venturing inland from the coast, we’ll pass through rural areas characterized by lush farmland and agricultural plantations. This region is known for its cultivation of sugarcane, coffee, and tropical fruits. We’ll witness vast fields of green, with occasional glimpses of farmers tending to their crops. It’s a great opportunity to observe the traditional agricultural practices and the livelihood of the local communities.
Arriving in Niquero, we’ll find a charming town with a laid-back atmosphere. Niquero is known for its historical significance as the landing point for the Granma yacht, which carried Castro and his rebels during the “Cuban Revolution”, in 1956. The town features a monument commemorating this event. Explore the streets, visit the local market, and interact with the friendly residents to get a taste of everyday life in this coastal town.

Breakfast, Lunch, Dinner
Standard Hotel

20171125 085436 Cuba Cycling Adventure Https://

Our adventure takes us to the heart of La Sierra Maestra. One of the most beautiful and naturally well-preserved places in Cuba, and the largest Mountain Range in the country, with El Pico Real del Turquino as its highest point at 1974 m/ 6476 ft.
We will ride on from Campechuela along sugarcane fields, cañaberales, heading towards Manzanillo, and from there to Bartolomé Masó. The second part of the route will lead us into the foothills of La Sierra Maestra mountains, offering glimpses of the majestic peaks in the distance. We will enjoy the scenic sight of the rolling hills and dense forests.
Our destination for the night is Villa Santo Domingo, a small town at some 300 m / 984 ft of altitude. It is the gate to two of the most attractive mountain trails in the country. One leading to the highest point of Cuba, “El Turquino” trail, and the other to La Comandancia de La Plata, or simply Fidel Castro’s Hideout. This Village introduces the beauty and significance of La Sierra Maestra mountains.

Breakfast, Lunch, Dinner
Standard Hotel
Day 6 :
To Bayamo

Bayamo, Cuba, Main Square

This morning we take jeeps and drive to the Alto del Naranjo where our tail begins. La Comandancia La Plata trail offers an unforgettable adventure through Cuba’s natural and historical treasures. To get to Castro’s Hideouts, it will take a hike of 6 km/ 3.7 mi on an uneven mountain trail, enjoying not only a physical adventure, but also an opportunity to delve into Cuba’s revolutionary history and witness the natural beauty of the region. It will lead us to the specific location where Fidel Castro’s hideout was situated in the Sierra Maestra mountains. The hideout, known as La Comandancia de la Plata, was a secret base and command center for the revolutionaries. Today, it serves as a museum and historical site, offering visitors a glimpse into the revolutionary struggle and the life of Castro during that time.
Right after this “historical hike” surrounded by exuberant nature, we get back to the Hotel in time for shower and lunch. After lunch, we drive to our next destination, Bayamo.
Bayamos foundation dates back to 1513, it was the second settlement created by the Conquistadores. Bayamo is also known as the birthplace of the Cuban nation, on October 10, 1868, Carlos Manuel de Céspedes, a prominent Cuban patriot, freed his slaves and invited them to join him as free men to fight and defeat the Spanish colonial rule, marking the start of the Ten Years’ War. It is also the place where the national anthem was written and sung for the first time, as it was where the first Flag and Republic in Arms were given to the Cuban People.

Breakfast, Lunch, Dinner
Standard Hotel
Day 7 :
El Salton

Villa El Salton In Santiago De Cuba

As our adventure continues, another day awaits. Our ride today can be challenging, but it will certainly be rewarding. This morning we leave behind Bayamos flat land and head into La Sierra Maestra again. Even when the Strava profile looks more like a rollercoaster, the first half of our route today will be only gently undulated. It is after Contramaestre that we will face some ups and downs.
Our destination today is Villa El Saltón. This tiny mountain Hotel provides a tranquil and scenic escape from the city, as it offers an opportunity to connect with nature and enjoy the beauty of the Cuban countryside.

Breakfast, Lunch, Dinner
Standard Hotel

Plaza De Marte In Santiago De Cuba

Our route today will begin with a short shuttle to Contramaestre. From there we ride along the very typical landscape and small communities and towns of this part of the province of Santiago de Cuba. As a characteristic ride in “Oriente”, a lot of green mixed with very brown soil will be the colors surrounding us, as well as the rolling undulations.
En route, we will stop at El Cobre. This little town is located in a picturesque setting surrounded by rolling hills and lush vegetation. The area offers beautiful views and provides an opportunity for visitors to enjoy the peaceful ambiance and natural beauty of the countryside.
Also known as the Basilica of Our Lady of Charity of El Cobre, a significant religious and cultural site is home to the patron saint of Cuba. The Virgin of Charity, also known as La Virgen de la Caridad del Cobre is the most revered religious icon in the country. The basilica is a pilgrimage site for many Cubans who come to pay homage and seek blessings from the Virgin.
It holds immense importance for the Cuban people as a place of spiritual reflection, and national pride. A visit to the El Cobre Basilica allows us to immerse ourselves in Cuban religious traditions, appreciate the architectural beauty, and witness the devotion and traditions of the Cuban people.

Breakfast, Lunch, Dinner
Standard Hotel

Bluest Of The Skies With The Whitest Of The Clouds Welcoming You. Travel!

This morning we wake up with home in mind, packing and making sure we take back all what we brought, as well as a new approach and perspective on reality. It will be very different, but hopefully this past week will have a lasting impact on us and how we approach life. Thanks for riding with us. Let’s do it again!



  • Accommodation in Private Hostels, and Hotels
  • All Breakfast and Meals + 1 Non-alcoholic Drink
  • Professional Staff: Tour Leader, Local Guide, Mechanic and Driver
  • Fully Vehicle Supported Bike Rides
  • Tour Bus for Airport pick-up and drop-off for MAIN GROUP'S FLIGHT


  • Gratuities for local STAFF
  • Flights in and out of Cuba
  • Airport pick-up and drop-off, if the flight is not the main group's one
  • Alcoholic Drinks

Trip Departure and Dates

November 7, 2024 - November 15, 2024 Guaranteed $0
20 Available
December 12, 2024 - December 20, 2024 Guaranteed $0
20 Available
January 9, 2025 - January 17, 2025 Guaranteed $0
20 Available
February 6, 2025 - February 14, 2025 Guaranteed $0
20 Available
March 6, 2025 - March 14, 2025 Guaranteed $0
20 Available
April 10, 2025 - April 18, 2025 Guaranteed $0
20 Available
May 8, 2025 - May 16, 2025 Available $0
20 Available

You can send your enquiry via the form below.

La Sierra Maestra, Oriente Highlights