Guaranteed departures for 4 or more people! Please inquire today to begin the booking process.
Origins of the Revolution - Cuba Walking Tour to the Sierra Maestra and Santiago de Cuba
In December 1956, Fidel and Raul Castro, along with Che Guevara, traveled by boat from Mexico to start an armed revolution against Batista’s army. Their landing went badly, and the survivors fled into the rugged Sierra Maestra. This steep and impressive mountain range towers over the southern coast of Cuba for some 80 miles and is home to mountain peasants who make a living with gardens, coffee, cocoa and determination. Our adventure explores the life of Fidel and the origins of the revolution as we visit the Castro family estate, hike the trails of the Sierra Maestra, and immerse ourselves in the vibrant city of Santiago de Cuba.
Older than Havana, Santiago was founded in 1514 by Diego Velazquez and was Cuba’s first capital. In 1898 Teddy Roosevelt gained fame here leading his Rough Riders to victory during the Spanish-American war. Castro’s revolution came to world attention when, on July 26, 1953, he and his band attacked the Moncada barracks. The city is a hotbed of exciting music, art and architecture and is considered by many as the most Caribbean part of Cuba. This is in part because some 30,000 French planters and merchants fled Haiti after the revolution there in 1791 and settled here, soon followed by black Haitians too. Slaves from Africa first landed here by the thousands, planting the roots of Cuba’s Afro-Cuban culture, replete with its music, myths and rituals. Set on a deep bay and flanked to the north by steep mountains, Santiago is a feast for the senses.
Images & Videos
Please book your own flights to Holguin, Cuba, currently served by American Airlines with daily flights. You can either arrive on Day 0 - the day before the tour start date, or on Day 1. If you arrive on Day 0 then you are responsible for your own airport transfer into the city. Taxis are readily available and cost about $25. We are happy to make your accommodation arrangements for you for the extra night. Since some guests may arrive on Day 1, if you arrive on Day 0, our office will inform you of the meeting time and place Day 1.
Once we have everyone together on Day 1, the tour will officially start with a walking tour of the city of Holguin.
Since all flights to Holguin originate in Miami, for many people it may work best to fly to Miami on Day 0, spend the night and continue to Holguin the next day. We are happy to offer guidance with scheduling your travel to and from Cuba, and our office staff is ready to answer any questions you may have.
Note: Travel in Cuba requires a flexible attitude. Our days are full, and as required by U.S. law, we have a full-time agenda of people-to-people activities. Cuba has it’s own beat and things don’t always run on time. The activities and visits listed are not guaranteed but we endeavor to do our best to provide the content intent of this Support for the Cuban People program. Visiting developing countries can be eye-opening and life-changing, and hopefully visiting Cuba is both. Accommodations may not be up to the standards you are used to. Sometimes the hot water or air conditioning doesn’t work. We ask all our guests to appreciate the authenticity of your cultural encounters as well as the people, food, culture, and adventures that are exceptional in their difference. Our local guide, along with your Cuba Unbound Tour Leader promise to do their best to make this a fascinating and educational experience.
Welcome to Cuba
Arrive Holguin on one of the mid-day flights. Meet your local guide and transfer into the city for lunch and your introduction to Cuba! We have an afternoon walking tour focused on the history of Holguin, Cuba’s fourth-largest city, known as the “City of Parks” and filled with charming colonial architecture.
Later in the afternoon we check into our accommodations, then enjoy a meal at one of the city’s fine paladars (private restaurants)
Driving South, into the Sierra Maestra
Note: Those participating in our Kayak East Tour join up with this tour mid-morning
After breakfast, we depart from Holguin and drive southeast, stopping near the town of Cueto to meet up with anyone from our Kayak East trip that is joining us. We head south on a road of tranquil agricultural scenery and through several towns and scenes of everyday life in Cuba. First up is a stop to visit Biran, the estate of the Castro family and birthplace of both Fidel and Raul. Their father, Angel, was quite a successful businessman and developed a small hamlet on the main railroad line that had a hotel, restaurant, cock-fighting ring and the family home. On our fascinating Support for the Cuban People tour with a local specialist, we learn more about the history of the Castro family and Fidel’s formative years.
We continue south and west to the town of Contramaestre and then delve deep into the mountains where the Revolution had its beginnings and the Third Front began. This is an area rich in both history and nature.Our destination is El Salton, a tropical resort set amid a thick jungle of green. Here we meet our local guide Carlos for a Support for the Cuban People walk among houses of local farmers. Many grow and process coffee and cocoa in these mountains, and we learn about their daily life on an easy two-mile walk. This is also a birder’s paradise, where the Cuban tody, hook-billed kites, Cuban Amazon parrots, and woodpeckers call to one ano
ther in the dense trees.
We enjoy a peaceful dinner and evening under the stars at our Casa.
Explore El Salton, waterfalls and swim
Today starts on our feet. With our local guide, who is well-versed in the endemic species that live here in the mountains, and knows all the locals, we hike along mountain paths. It’s a day mixed with learning about the forest ecosystem and visiting with local Cuban farmers and villagers. Royal palms, oaks and ferns dot the landscape, and orchids dangle from the trees. Birders will also delight in this tropical forest, replete with hummingbirds, thrushes, falcons and many of the endemic species of Cuba.
A highlight of the day will be a visit to a local school high in the mountains. Another will be lunch with a local family in a simple home surrounded by coffee, grazing areas and fruit trees. People here live simply and close to the land. It’s a fascinating glimpse into their lives where traditional open fire kitchens, gardens and farm animals are at the core.
Our afternoon takes us to a lovely swimming hole for a dip in refreshing waters. Then we return to our Casa for another evening of music, dinner and star-gazing.
From Mountains to Sea - Santiago de Cuba
Today we have an exciting and remote drive through the Sierra Maestra, over a pass and down to the coast with four-wheel drive jeeps. The drive gets us deep into the heart of the Sierra Maestra with fantastic views of the Caribbean as we descend from the mountain pass to the sea. We make plenty of stops for photography and have lunch along the way.
Once we arrive at the coast we head east towards Santiago, perhaps stopping for a dip in the ocean on the way. We settle into our accommodations, then head out for a great dinner at a local paladar.
*Note that if we are unable to arrange a vehicle for this mountain transfer, we will instead drive via mostly paved roads from El Salton to Santiago and begin our touring of the city at that point.
Explore Santiago de Cuba
Santiago de Cuba is an important port city and Cuba’s second biggest city, next to Havana. It shares a similar pulsating energy but grooves to its own beat. It’s hardly surprising that many consider Santiago the cradle of Cuban music, and the son originated here.
Today is a day to explore this fascinating city. We start with a visit to a cigar factory where the legendary Cohibas and other brands are rolled and shaped. This is an intriguing look into the complex process that is required from tobacco harvest to final product. Next up, we visit the Plaza de la Revolucion, with the impressive and towering Monumento Antonio Maceo cast in bronze. Then it’s on to the Cementerio de Santa Ifigenia with the tomb of Jose Marti, hero of Cuban independence and more recently, that of Fidel Castro. We watch the changing of the guard ceremony and explore the graves of other famous Cubans including the resting place of Compay Segundo, the legendary singer and guitarist who wrote the Chan Chan that we were introduced to earlier in our journey.
Ater lunch, we visit San Juan Hill where Teddy Roosevelt and the Rough Riders rose to glory and defeated the Spanish in the Spanish-American War of 1898. Bronze plaques have lists of the U.S. soldiers killed in the war. We learn about this ilittle-known chapter in our history, then head to a special musical performance where we learn about Santiago’s musical heritage. Our visit to the Casa de la Trova where Paul McCartney once made an appearance is sure to get you on your feet and dancing! This is a state sponsored music salon where a cadre of singers and musicians perform. Its freeform musicality showcases a nostalgia for the days of troubadours and the open welcoming of any and all performers. Sounds of the street mingle with the melodies, becoming part of the ambience. Dinner is another Cuban feast.
A History Lesson Through Santiago de Cuba
We take the opportunity to further explore Santiago today as we head out on a walking tour of the city. Santiago’s proximity to tropical islands like Jamaica has infused the city with an urbane glamour and vibrant Afro-Caribbean culture evident throughout the streets. It’s also a cultural capital that has played pivotal roles in Castro’s revolution and the Bacardí rum business.
Our walking tour takes us to Parque Céspedes, a quintessential Cuban square where colonial architecture is foregrounded by troubadours smoking cigars and writers seek literary inspiration in terrace bars. A statue of Carlos Manuel de Céspedes, the man who incited the 1868 rebellion, overlooks the modern bustle. Next to the park we find the Diego Velázquez Museum, home of Cuba’s first governor built in 1516 reputed to be Cuba’s oldest house. We amble on to the Museo del Ron that explores the history and production of Cuba’s most popular liquor. Our local expert guide brings these places all to life while providing an excellent educational exchange.
After lunch our exploration continues with a visit to the Moncada barracks where Castro’s revolution got off to a failed start in 1953. We enjoy a stroll down the vehicle-free Boulevard for some souvenir shopping, and on to the El Tivoli neighborhood, named by French plantation owners who had fled Haiti during the Haitian slave revolution and settled here. Narrow streets crisscross steep hills that head towards the bay and one of Cuba’s only brewpubs where we enjoy a beer or soda before returning to our casa.
In the evening we have our farewell dinner and for those who want, enjoy a night in the energetic town.
This morning transfer on your own to the Santiago Airport or a three-hour return to the Holguin airport. As of April 2023, American Airlines has a daily late-morning flight from Santiago de Cuba to Miami. If necessary we can arrange a taxi for an extra fee to return you to Holguin.
*Note: Travel in Cuba requires a flexible attitude. Our days are full, and as required by U.S. law, we have a full-time agenda of Support for the Cuban People activities. Cuba has it’s own beat and things don’t always run on time. The activities and visits listed are not guaranteed but we endeavor to do our best to provide the content intent of this Support for the Cuban People program. Visiting developing countries can be eye-opening and life-changing, and hopefully visiting Cuba is both. Accommodations may not be up to the standards you are used to. Sometimes the hot water or air conditioning doesn’t work. We ask all our guests to appreciate the authenticity of your cultural encounters as well as the people, food, culture, and adventures that are exceptional in their differences. Our local guide, along with your Cuba Unbound Tour Leader promise to do their best to make this a fascinating and educational experience.
Dates & Rates
|Dates||Adult (USD)||Child (USD)|
|Jan 01, 2023 to Dec 31, 2023 |
Guaranteed departures for 4 or more people
|Jan 01, 2024 to Dec 31, 2024 |
Guaranteed departures for 4 or more people
Dates: Guaranteed departures for 4 or more people! Please inquire today to begin the booking process.
Rates 2023 Season:
$2490 per person
Single Supplement: $350
Rates 2024 Season:
$2790 per person
Single Supplement: $500
Note - This trip works well as an add-on to our Kayaking in the Wake of Christopher Columbus tour.
Up to 16 spaces available on each tour (depending on the number of solo travelers and available accommodations)
If you are traveling solo and prefer private accommodations (pending availability) you may elect to pay the single supplement fee. If you are traveling solo and wish to be paired up with another solo traveler of the same gender in order to avoid the single supplement fee, please let your Adventure Consultant know at the time of booking. We will do our best to find another traveler to pair you with, however if there is not another solo traveler of the same gender willing to share on your trip, you will be charged the single supplement fee.
Optional Pre-Tour Extension:
Extend your exploration of Eastern Cuba with a our Eastern Cuba kayaking tour! One of Outside Magazine's top 25 tours of 2018.
**Note: We can guarantee trips for 2 with a supplement of $300 per person on trips between May 1 and December 15.
- Experienced English-speaking guide(s)
- Specialized activity guides based on activity of trip (kayaking, biking, hiking, etc.)
- Specialized equipment needed for activities such as kayaks, bikes, helmets, paddles, personal flotation devices, etc.
- Private pre-tour orientation meeting
- Cuba Unbound hand-crafted itineraries
- Accommodations as noted in the itinerary
- All meals as noted in itinerary
- Certification of travel to Cuba under the U.S. Department of Treasury general license
- Small group size (Custom tours for 2, group tours are 16-18)
- All entrance fees to include events and activities
- All in-country ground transportation
- Clean drinking water available at all times
- Gratuities for presenters, luggage handling, and restaurant staff
- Cuba Visa (a $80-120 value)
- Round-trip air to/from Cuba
- Transfers to the airport at the end of the tour
- Guide and driver gratuities
- Personal expenses such as souvenirs, gifts, alcoholic beverages, additional entertainment outside the standard itinerary, and incidentals
FAQ & More
Yes, you can travel to Cuba as a US citizen! Although, the United States is the only country that restricts its citizens from traveling to Cuba for touristic reasons, however, the U.S. does allow travel to Cuba under one of 12 permitted travel categories. Of these categories, most of our travelers are traveling under either "Support for the Cuban People" or "Educational People-to-People" travel.
For more information on Cuba travel entry requirements, please see here.
This is something you'll hear in Cuba a lot. A casa particular is a private accommodation or private homestay in Cuba, very similar to a bed and breakfast, although it can also take the form of vacation rental. .
We walk between two and five miles. Our pace is casual and most walks have little to no elevation gain. Most of the walking will be done during the day in the cities that we will visit. There will be plenty of breaks to take pictures and to learn about the history of the area from our specialized guides. The hikes in the parks will also be guided by experts and the pace will be set depending on the group's abilities.
Trails are generally well maintained, but loose rock and dirt are common. All paths may be slippery when wet. Good walking shoes or boots are essential; walking poles are not necessary. In the cities where we walk, careful attention to holes in the sidewalks or streets is critical.
We will provide clean drinking water at all times during the tour!