This Cuba cycling tour we call "Quintessential Cuba." A tour designed and inspired by cycle enthusiasts.
Cuba creates legends and imbues folklore. Everyday items such as a rolled cigar, a glass of rum spiked with sugarcane juice, a colorful classic car become more—gain a near-mythical status and a story that endured in the American consciousness even when Cuba’s doors were closed. With its pulsating physicality, soulful music, and evocative landscapes, it’s not surprising that Hemingway, Graham Greene, Sinatra, and Churchill—legends in their own right—were drawn to Cuba.
Join us on our new Cuba cycling tour and see for yourself why Cuba is not only breathtaking, but legendary. Explore vivacious Havana and its streets paved in revolution. Pedal through spring green fields of tobacco plants where the haunting sounds of vagueros harmonize with the rustling leaves. Stand in front of caves whose eroded faces tell stories of former indigenous inhabitants hiding from invaders or towering walls of limestone in Valle de Viñales. Cycle along white-sand beaches, by crumbling but lavish buildings, and through verdant biospheres on a trip that might leave you speechless even as it turns you into a storyteller.
Our cycling tour through western Cuba takes you off the well-traveled tourist track and onto roads where Cuba’s history may not have been made, but where it was lived every day. It reveals to you to Cuba’s true resource, it’s true legend: its people.
*Compare this tour with our other cycle tour in Cuba: Classic Cuba Bike Tour ~ Experience Biking through Cuba's Corazón
Images & Videos
Commercial flights from the United States to Cuba are the standard mode of travel between the two countries, and we ask that our guests book their own travel between the U.S. and Havana. This tour will begin in Havana at approximately 11:00 AM on Day 1. Our meeting point on Day 1 will be Havana's Jose Marti International Airport where your Tour Leader and local guides will meet you to begin your tour.
If you are unable to fly all the way to Havana on Day 1 with an arrival before 11:00 AM, we recommend that you consider a "Day 0" for your tour and choose either of the following:
Travel to Havana on Day 0. With this option, we recommend that you overnight in a casa particular (a private home with rooms for rent) of your choosing and make your way back to the Havana Airport to meet your Tour Leader, guides, and fellow travelers the next morning.
Travel to Miami on Day 0. With this option, we recommend that you overnight in Miami and take a flight to Havana on the morning of Day 1.
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 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 difference. Our local guide, along with your Cuba Unbound Tour Leader promise to do their best to make this a fascinating and educational experience.
Arrive in Havana!
Bienvenido a Cuba! Once we’ve all gathered at the Havana airport, we travel deeper into Havana for our first day of Cuban adventure.
We begin our tour by finding our way to a local paladar, a privately owned restaurant, where we can delve into Cuban culture by trying its Caribbean-tinged cuisine. Once we’ve satisfied our appetites, we begin our walking tour of the city. The highlight of our afternoon is Habana Vieja, or Colonial/Old Habana. It’s a burgeoning downtown area where it’s turbulent history is evident in every colonial plaza and Cuba’s future can be seen on the still-bustling streets. Unlike many other colonial city-centers throughout the island, Habana Vieja appears very much sentient to the present rather than being lolled into a slumbering past. Rich in history, colorful in daily life, the vibrancy is palpable.
After a full afternoon exploring Havana Vieja’s many sights, we sit down to dinner at another local paladar. Then, you have the choice to return to your casa particular (private home) for a good night’s rest in preparation for tomorrow or stay out a bit to see what the music scene in Havana is all about.
Cycle Havana to Las Terrazas
We rise early and drive out of the urban sprawl toward San Antonio de Los Baños, known to Cubans as the capital of humor due to the city’s idiosyncratic humor museum and film school founded in part by famous novelist Gabriel García Márquez. We don’t spend much time in the eccentric town as we start our day’s cycle toward Las Terrazas.
Our peaceful ride today takes us past Vereda, Caimito, Guayabal and Cayajabos. The undulating path is fairly smooth as we travel along verdant citrus plantations and plots of various other crops. As Artemisa Province is one of the best citrus producers in the country, there are plenty of cooperatives peppering the towns and we stop at one to sample some of the famed fruit as well as meet with a manager. In this local experience, learn about Cuba’s agriculture, the role of cooperatives in the market, and the people who manage these resources—with a fresh snack on the side—before we continue on our ride.
Our trail concludes in Las Terrazas, a UNESCO protected biosphere originally created as part of Castro’s 1968 reforestation proposal. The region, which had been over-logged since the enterprising days of Spanish conquistadors and coffee plantations, is now a verdant haven for over 117 different bird species including the endemic tocororo and zorzal. Stretch your legs after a day on the cycle and explore the flourishing pastures. If we have time, we may visit a local artist workshop where we learn about how politics of the environment blend with artistic passions within the small community.
Later, we make our way to our accommodations for the evening. One option may be Hotel Moka, which embodies the spirit of Las Terrazas with its teak tree backdrop and 100-year-old rain tree thrusting up through the lobby’s rooftop. Or we stay in local area casa particulars. Either way, enjoy the cool, invigorating night air as well as a delectable dinner before turning in.
Biking Distance: 30.9 Miles
Elevation: + 1233 / - 939 ft.
Cycle Las Terrazas to Viñales
Today we cycle rough roads, rolling roads, and smooth roads that take you through some of Cuba’s most lush landscapes. It’s a fun ride with new adventures at every turn! We set off early, and we pedal through La Sierra del Rosario Biosphere Reserve and stretches of forests and grasslands, rounded hills and waving royal palm trees. Keep an eye out for some incredible rock formations jutting out of the earth. Our meandering path takes us to Bahía Honda, where we stop for lunch, and passes through several beautiful towns such as Cabañas, Palma Rubia, and La Palma as we make our way to Viñales.
We pause at La Palma, where we are picked up and transferred to Viñales, a region encircled by the misty, pine-covered hills of the Sierra de los Órganos. Valley de Viñales has a fantastical appearance with its stocky limestone mogotes abruptly rearing from flat plains and labyrinths of caves secreted away in cragged overhangs. Explore some nearby paths and take in the immersive scenery before we get some well-deserved R&R with dinner and a drink before bed.
Biking Distance: 38.4 Miles
Elevation: + 1953 / - 2400 ft.
Explore Puerto Esperanza and Viñales
We enjoy a hearty breakfast before once again climbing onto our bikes to explore more of the sprawling karst landscape. On our way toward Puerto Esperanza, we peddle our way through plantations with bright green swathes of tobacco leaves and recently turned rust-colored earth, rural villages with their sillo bedecked porches. It’s a peaceful morning ride through one of Cuba’s most serene corners.
Around lunchtime we land in the Puerto Esperanza, a fishing village which serves as a primary port for Viñales. Expansive mango trees said to have been planted in the 1800s bound the entry road, and the gentle crash of waves greets your entrance into the placid town largely untouched by the last 50 years. We stop for lunch in the seafront town before getting picked up for a transfer back to our lodgings in Viñales.
Once we’re back in the valley with the afternoon before us, we have the opportunity to walk along the arbitrary “train systems” that unfurl throughout the valley or visit a nearby organic farm. The trail systems may lead to the rising, vertical walls of mogotes, the pock-marked faces of the caverns, or obscure river systems—arresting sights that comprise the unique landscape. Visiting an organic farm allows us to engage with the local people who tend to the land that sustains them and gives us insight into their everyday livelihood.
Later, we enjoy another dinner of fresh ingredients prepared with Cuban authenticity before retiring for the evening.
Biking Distance: 20.9 Miles
Elevation: + 853 / - 1295 ft.
Cycle Viñales to Pinar del Río
Greet the morning in verdant Viñales before we transfer to Puente de Cabezas, a rural town surrounded by swathes of undulating green fields. Our cycle today takes us through the San Carlos Valley, where you’ll be surrounded by incredible views. Limestone bluffs blanketed in foliage look over isolated huts and rust-colored tobacco fields. Palm fringes rustle in the wind and birds call to one another. With the smooth road unwinding before you, you can soak in the bucolic scenery as we cycle along and do some exploring when we pause for a box lunch en route.
Our ride takes us to Cuba’s tobacco mecca San Juan y Martínez, whose abundant rainfall produces some of the country’s finest tobacco leaves. There, we take to our feet and visit the Alejandro Robaina Tobacco Planation. Though the vegas (fields) have been producing quality tobacco since 1845, the Vegas Robaina cigars didn’t launch into international acclaim until the late 1990s. Tour the grounds and gain insight into the cigar-production process from sprouting plant to fragrant-wrapper rolled treat.
After our tour, we continue our Cuba cycling tour to Pinar del Río. The city lives up to its name, as pines adorn its river banks. Though the city has a bit of a reputation for its wealth of jinteros, it has an intriguing energy and an abundance of well-maintained neoclassical architecture. Check into your casa before meeting for dinner at a local restaurant.
Biking Distance: 43 Miles
Elevation: + 1467 / - 1760 ft.
Cycle Pinar del Río to San Diego de Los Banos and shuttle to Havana
We continue our travels through rural Cuba as our cycle today take us along the La Carretera Central highway passing through Herradura, Capilla, and Paseo Real de San Diego until we arrive in Fierro. We enjoy a picnic at a scenic spot en route and have the opportunity for a supportive interaction with local beekeepers. Other surprises await us as we discover and learn from local Cubans we meet along the way.
After our ride we board our bus and head into Havana for the night. After getting settled into one of the area's great casa particulars, we dine of one of the city’s fine paladars and for those who wish, there’s plenty of music to explore later in the evening.
Biking Distance: 31.8 Miles
Elevation: + 1175 / - 1122 ft.
A Day in Havana
Today is a day on foot as we explore Havana. In the morning we drive a short distance west to Jaimanitas where we find the fantasy-world of artist José Rodriguez Fuster. Fuster took the streets of the formerly average town and shaped it into a widespread art exhibition Picasso would have felt at home in. We walk through Fusterlandia and witness the incredible world where roofs, doorways, benches, and city blocks become expressions of the artist and iconic Cuban images.
Driving east back through Miramar, we see leafy suburbs where embassies line the streets, and upscale Havana plays. Our next stop is the the Museo de Ernesto Hemingway located in his former home at Finca Vigía. With a local guide, we tour the restored facilities to gain insight the life and mind of Cuba’s favorite literary expatriate. Afterwards we visit the seaside hamlet of Cojimar where Hemingway kept his boat, Pilar, and we find a couple of excellent paladars to choose from for lunch.
In the afternoon we have time to explore more of old Havana on foot. Walk along the Malecón, amble along the narrow streets of Habana Vieja, and if you wish, visit one of several excellent museums in the city. It’s an immersive day of architecture, history, and the ever-evolving Cuban culture as we follow the labyrinthine paths of Havana’s history.
Late in the day, we start our final night out on the town. We explore the city as night falls as Cubans do—in classic cars that haven’t lost their 1950s glamour—before making our way to a paladar for dinner. Enjoy Havana’s salsa-filled nightlife before returning to your casa to rest up for tomorrow’s flight!
*Optional Ride 10-15 miles on mostly level terrain
After breakfast transfer to the airport on your own (we will help you arrange a taxi) or join our two-day Havana Extension!
*Taxis to the airport are approximately $25-30 for up to 3 people with luggage.
Note: The listed activities and itinerary above may undergo some changes as they are contingent upon factors such as the availability of guest speakers, weather, and transportation. In such cases, we always attempt to substitute similar activities that maintain our tour’s focus to promote independent activity intended to strengthen civil society in Cuba through cultural exchanges, which also furthers your Cuban experience.
Dates & Rates
**Our trips can also be booked on-demand for any dates for small and large groups. Please inquire with us to start the booking process today!
Rates: $3,885.00 per person*
Note: Christmas departures have a supplemental cost ($300 per person) due to our increased prices for accommodations.
Up to 16 spaces available on each tour (depending on the number of solo travelers and available accommodations)
Single Supplement: $500
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.
• 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
• Round-trip air to/from Cuba
• Cuba Tourist Visa Fee (ranges from $50-$100 depending on where you buy it)
• Guide and driver gratuities
• Personal expenses such as souvenirs, gifts, alcoholic beverages, additional entertainment outside the standard itinerary, and incidentals
FAQ & More
The Support for the Cuban People travel category is a Cuba travel initiative which permits Americans to travel to Cuba with the intention of promoting meaninful encounters between travelers and the Cuban people. Each program emphasizes experiencing and interacting with private sector Cuban artists, conservationists, naturalists, musicians, entrepreneurs, and culinary experts. Traveling through Cuba with a Support for the Cuban People emphasis means our itineraries will take participants to places that the typical tourist seldom sees or knows to look for. Rather, our trips take participants to communities, organizations, and places that will not only be educational and enlightening, but culturally enriching for both parties involved.
The good news is that you don't need extensive cycling experience to enjoy our tour. However, you’ll want to spend some time training on a bike before your trip. Work your strength up to riding the same daily distances that we will cover in our tour while carrying the same gear you plan to travel with.
A trained guide will be able to make repairs to bikes on the tour and will have the necessary tools and equipment.
Our Quintessential Cycling tour takes place in Western Cuba. The towns and villages that you will visit include Viñales, Pinar del Rio and Havana. This tour is more mountainous and rural in nature. This tour is where you get to see Cuba’s agricultural sector and tobacco farms.
The Classic Cuba Cycling tour travels through central Cuba to some large cities like Matanzas, Remedios, Trinidad and Cienfuegos. This tour is considered less challenging than our other tour because of easier elevation. Through this tour you will get to experience a more city-centered travel experience.
199.6 miles over six days.
See Website for specifics.
There are currently no accurate numbers. Quintessential Cuba is our more challenging bike tour and as such will have more elevation gain and loss as well as more challenging riding in general. This western route will tour the rural areas of Viñales and San Carlos valleys with some small climbs through the Sierra de los Órganos.
We will be using the FX S 4 Trek Bike designed for both paved and unpaved riding.
This tour is on 90% paved roads, but these roads do tend to be a bit rough, uneven, and have large pot holes. The unpaved portions are hard-packed, and there is no off-road or trail riding.
Yes! But we unfortunately cannot offer a discount for guests who choose to bring their own bike. In addition, you will need to bring any spare parts, tubes, etc. as these will not be available in Cuba. Checking your bike to Cuba must fall under specific guidelines for our charter company, as follows:
- Boxes and irregularly shaped luggage will be charged at $3 per lb plus $20 per piece,
- No piece of luggage may weigh over 70 lbs.
If you do not take our charter flight to Havana, please be sure to familiarize yourself with the policies for checking a bike for the airline with which you are flying.
There is a support tour bus that will be hauling luggage and to aid riders available at all times.
There will be options to rest in the van for anyone who wants to take a break and/or hitch a ride to the next location. We will definitely take breaks as needed (how often and duration will depend on the group), but there is always an option of taking a break in the support van.
We will provide clean drinking water at all times during the tour!
We will provide helmets, but you are welcome to bring your own if you prefer.
You are welcome to bring your own pedals and shoes as we will have a bike technician who can swap out pedals at the beginning of the tour.