Colorful Cuba

February 2020 • 11 Days • Approx $3900-$4100

We’ll offer 2 departures in February 2020 if there is enough interest!

Cuba – one of our most fascinating destinations yet! We are excited to present our new Adventure to Cuba, a beautiful island with a complicated yet rich culture and unique historical narrative. Join us in 2020 as we explore the city streets and nature trails of the Pearl of the Antilles!

Check back soon! This itinerary will be finalized shortly! 

Traveler Rewards Program: New Travelers receive a $300 discount on the Colorful Cuba tour! Returning travelers receive our Alumni Traveler Discount of 5-10% off the main tour price. Terms, exclusions and conditions apply. Check out our Traveler Rewards page for more details.

Now accepting Early Bird deposits on this new tour! An Early Bird is a $50 deposit that holds your spot during the planning stages of a trip, when we don’t have a set itinerary or dates. Early Birds are always refundable!

Once under Spanish rule, then briefly a US protectorate, Cuba gained formal independence in 1902. Following the Cuban Revolution and the Castro regime of communism, the island became an unreachable destination for American visitors since the 1960s. Turbulent relations heightened during the Cuban Missile Crisis and continued through the last half of the 20th century during the Cold War. Recent thawing of diplomatic relations between the US and Cuba is now allowing certain kinds of cultural travel for Americans for the first time in decades. Cuba is still a communist nation and our visit will have unusual controls to deal with. We will be working, however, with experts on travel to Cuba and are excited to share the itinerary we have developed with them!


  • Viñales Valley – a UNESCO World Heritage Site, Viñales Valley is considered one of the best nature spots in Cuba. Agriculture and especially tobacco cultivation is the main activity here in this scenic valley, augmented by dramatic limestone monoliths known as mogotes.
  • Cienfuegos – Nicknamed “The Pearl of the South” this city is known for its French colonial-era buildings, is Cuba’s third largest port, and offers a historic center which has been designated a UNESCO World Heritage Site.
  • Fusterlandia – A colorful neighborhood decorated by Cuban artist José Fuster, who coated his neighbors’ homes in whimsical mosaic sculptures and murals.
  • Trinidad – A UNESCO World Heritage Site, Trinidad is Cuba’s third oldest city with one of its best preserved colonial centers. It’s a great place to wander and enjoy the brightly colored buildings, cobblestone streets, fun markets, and only-in-Cuba street musicians.
  • Havana by Convertible Car – We’ll check out a tour of Havana’s streets, taken in 1950s classic American convertibles.
  • Caribbean Coastal Vistas & National Parks – We have multiple walks available in reserves and protected areas and ample opportunities to soak in the clear, turquoise waters of the Caribbean.
  • And so much more!

This is a draft itinerary. Details will be finalized soon!


  • Airport to hotel transfers on first and last day
  • All land travel as outlined by motorcoach
  • Accommodations in a blend of hotels and casa particulares (private homes)**
  • 20 meals: all breakfasts, 3 lunches, and 7 dinners as denoted (BLD)
  • 10 walks routes as listed
  • Walking fees for those collecting walking credit
  • WAI guide service throughout (2 guides)
  • Cultural & historical expertise of national guide throughout
  • Local guide assistance in several national parks and reserves
  • All tipping for local guides, coach drivers, and group meals
  • Pricing is based on double occupancy. A limited number of single rooms are available for a supplement.

Activities/Visits to:

  • Classic Car tour
  • San Carlos de la Cabana Fortress
  • Fusterlandia
  • Soroa Orchid Garden
  • Viñales National Park
  • Viñales tobacco farm visit
  • Cenote swimming experience
  • Ciénaga de Zapata National Park
  • Museo Giron – Bay of Pigs
  • Palacio de Valle
  • Coffee farm lunch
  • Topas de Collantes National Park
  • Trinidad Architectural Museum
  • Valle de los Ingenios sugar mill visit
  • Che Guevara Mausoleum

Optional Excursions:

  • Malecon & More Havana Walk – DAY 1
  • Museum of the Revolution – DAY 1
  • Salsa Dance Lessons – DAY 9
  • Cubano National Park Walk – DAY 9

** The Cuban government allows private citizens to rent rooms in their homes to tourists. In many, if not most cases, casa particulares are a higher value option than hotels, which are all government-owned. Of the 10 nights on this trip, 4 will be in hotels and 6 will be in casa particulares. The group will be split up into homes as close together as possible. All rooms will have private facilities en suite and air conditioning. Breakfasts are served in the individual homes.

Adventure Pace

Tour Pace: 1 2 3 4 5
Walk Challenge: 1 2 3 4 5

Important Info

Group Size

An average of 24-28 travelers


Accommodations in a blend of hotels and casa particulares (private homes)


20 meals: all breakfasts, 3 lunches, and 7 dinners


Not Included. Travelers will fly into and out of Havana, Cuba.



Traveler Age

Our travelers usually range from 50–75 years of age. All ages welcome!

Your Guides

WAI Guide Dan FriesenDan Friesen has been guiding tours for over 25 years on all 7 continents. He has hiked the Great Wall of China, hobnobbed with penguins in Antarctica, felt the spray of Iguazu Falls in Brazil, yodeled from the heights of the Swiss Alps, and walked the ruins of majestic Machu Picchu. Dan will be accompanied by a Walking Adventures assistant and national guide on this tour. He looks forward to sharing the intriguing history, culture and natural wonders of Cuba with you!


This is a draft itinerary. Details will be finalized soon!

Click on each day for more details.

Day 1: Arrive Havana (D)

Optional Malecon & More Havana Walk – 7 km, rated 1A

We rendezvous in sunny Havana today for one of the most unusual walking adventures we’ve yet experienced. We look forward to sharing an unforgettable array of activities with the Cuban people through a cornucopia of cultural connections and excursions. We also hope to discover the unspoiled natural wonders of this Caribbean island, inhabited by a society that seems to be working its way through a late-19th to mid-20th century time warp.

Optional Malecon & More Havana Walk and Museum of the Revolution: Travelers who opt to arrive early are invited to join us for a walk along sections of the 7-kilometer-long Malecon (esplanade) that borders the Atlantic. The route takes us into Centro Havana for an optional visit to the Museum of the Revolution to see this piece of history from a different point of view. We finish with a stroll down the Paseo del Prado to Central Park and the Capitolio, originally the home of the Cuban Congress, currently under renovation to serve as the new home for Cuba’s National Assembly. Price TBA

Later this evening, we meet for a Welcome Orientation and dinner at Hotel Nacional de Cuba, Havana’s most famous hotel and a magnet for foreign celebrities and diplomats during the pre-Castro years.

Day 2: Activities in Havana (BL)

Historic Havana Walk – 6 km, rated 1B

Our day begins with a memorable tour of the city by convertible classic car. Perhaps the most iconic images of Cuba are these wonderfully restored automobiles from the 50s and 60s. Our vintage vehicles deposit us at the entrance to San Carlos de la Cabaña Fortress on the opposite side of Havana Bay to start today’s walk. This late 18th century behemoth is the third largest fortress in the Americas and sits atop the cliff overlooking Havana, providing outstanding views of the harbor and the city and contributing an intriguing piece of Cuba’s history. From La Cabaña, our trail takes us to the fishing community of Casa Blanca to ride the local pedestrian ferry across the harbor. We disembark in Habana Vieja – Old Havana – to continue our walk through the oldest parts of the city, dating back to 1514! Of primary interest are Havana’s lovely squares – four of which are featured on our walk. Lunch in Old Havana is followed by free time to explore this fascinating combination of wonderful architectural restoration and rampant decay, overlaid with a vibrant cultural vibe that continues into the night. The late afternoon and evening are free to relax and wander the area near our hotel, or enjoy its spacious grounds.

Day 3: Havana – Viñales (BL)

Viñales Viewpoint to Valley Walk – 3 km, rated 2B

Jaimanitas is a small fishing village south of Havana better known as Fusterlandia after its most famous son, Cuban artist José Fuster. Inspired by Picasso and the modernistic images of Antoni Gaudi, Fuster transformed his home and neighborhood with a whimsical array of colorful tiles. A short stop here prepares us for color of a more natural sort at the Soroa Orchid Garden. Created by Spaniard Tomás Felipe Camacho in the 1940s to honor his deceased daughter, this Eden-like hillside is covered with over 20,000 plants, including 700 species of orchids (of the more than 35,000 worldwide!). Our day ends with more scenic driving into the very different landscapes of Viñales Valley and Viñales National Park. From the viewpoint overlooking the valley, our walk of the day descends through forest and field, passing tobacco farms and other agricultural pursuits, and winding our way around the signature geological wonders of the valley – mogotes. These unique limestone mounds pop up from the valley floor reaching heights of over 1000 feet. We spend the next two evenings in the town of Viñales in casa particulares, private guesthouses, enjoying the hospitality of the burgeoning private sector of tourism in Cuba.

Day 4: Activities in Viñales National Park (BD)

Viñales Mogotes & Prehistoric Mural Walk – 7 km, rated 1B
Viñales Tobacco Farm Walk – 4 km, rated 1B

A hearty homemade breakfast prepares us for a day of exploration in the UNESCO World Heritage Site of Viñales National Park. Our first walk nearly circumnavigates one of the larger mogotes, passing farmers at work in the fields (probably behind a pair of oxen) and offering possible sightings of some of Cuba’s 28 endemic bird species. We finish with some of Cuba’s best piña coladas then return to Viñales and our guesthouses for a mid-day break and a chance to explore this interesting town. Later this afternoon, we head for a different part of the valley and a walk to a more remote tobacco farm. Here, we learn the time-honored techniques of tobacco farming and unique aspects of a state-controlled agricultural sector. Dinner this evening is at a picturesque organic farm offering sweeping views over the valley from a rambling hilltop farmhouse.

Day 5: Viñales – Playa Larga (BD)

We leave western Cuba this morning for a lengthy but intriguing drive to the Bay of Pigs. En route, we stop for a no-host lunch and a nostalgic window into the sugar cane industry in Cuba, along with the trusty trains that carried the cane. Cenotes (water-filled sinkholes) are a geological phenomenon of Cuba’s Caribbean coast and this afternoon offers the opportunity to swim in one, or in the turquoise waters of the Caribbean across the road. Our home for the next two nights is Playa Larga, a bustling village on the shores of Bahía de Cochinos, known to Americans as the infamous Bay of Pigs. Private guesthouses are the best, and only viable, option for lodging here, offering delightful opportunities to stroll the village and the dreamy, palm-lined Caribbean beach. Political reminders of the unsuccessful American-backed 1961 invasion by Cuban exiles are strewn throughout this part of Cuba, but today’s beautiful beaches and natural setting bely the violence and political turmoil of this chapter of the Cuban story.

Day 6: Activities from Playa Larga (BD)

Ciénaga de Zapata Walk – 6 km, rated 1A
Gran Park Natural Montemar Walk – 2 km, rated 2C

We are up with the birds this morning for a walk to see flamingos. Actually, we need our coach to drive us through Zapata National Park to the remote lagoon where colonies of these iconic pink wading birds congregate in large numbers. Later today, we drive along the coast to Museo Giron for insight into the Bay of Pigs Invasion from the Cuban point of view. On the return journey to Playa Larga, walkers are invited to join us on a trail through a completely different eco system, over challenging sections of fossilized coral surfaces to a pair of remote cenotes nestled away in Gran Park Natural Montemar. Those who opt out will return to our guesthouses where we rendezvous this evening for dinner together.

Day 7: Playa Larga – Cienfuegos (BD)

Zapata National Park Walk – 5 km, rated 1A
Cienfuegos Bay Walk – 5 km, rated 1A

We visit one more corner of magical Zapata National Park this morning on an early morning trail in the company of an informative park ranger. This is an easy route through a type of subtropical forest we’ve not yet seen. It’s a showcase for Cuba’s colorful endemic birds and it’s likely that we’ll see several species, possibly even the world’s smallest bird – the bee hummingbird. Later this morning we arrive in Cienfuegos, a city with a UNESCO-listed colonial core set on one of Cuba’s larger bays. Following time for lunch, we start today’s second walk from Parque José Marti, lined with an impressive grouping of restored 19th centuries monuments, including Tomas Terry Theatre, Museo Histórico, and Cuba’s only triumphal arch, evidence that Cienfuegos is Cuba’s only French-founded city. Our route takes us along the Malecon, with nearly non-stop views of the harbor, to Punta Gorda, a narrow spit of land poking south into Cienfuegos Bay. Our walk ends with a break for refreshment on the terrace of Palacio de Valle, an eclectic blend of Gothic, Venetian and Neo-Moorish motifs funded by one of Cuba’s wealthiest sugar magnates in the early 20th century.

Day 8: Cienfuegos – Trinidad (BLD)

Topas de Collantes Walk – 5 km, rated 2B

Today’s drive takes us into the mountains of Topes de Collantes National Park. Coffee is Cuba’s second major export crop, along with tobacco, and we stop en route to the National Park at a humble coffee farmhouse to have lunch with a local family. The simplicity of the kitchen and home, set on a hillside along a mountain stream, and the hospitality of our hosts, make this one of the more memorable stops on our journey through Cuba. The walk of the day is in the national park, and features a pair of delightful waterfalls and a rich variety of vegetation, with more opportunities to enjoy Cuba’s aviary wealth. As we descend through Topes de Collantes to Trinidad, the panoramas are some of the loveliest of our trip. Trinidad is Cuba’s third oldest town, and after checking into our private guesthouses, we stroll into the oldest parts of town for tonight’s dinner in yet another UNESCO World Heritage setting.

Day 9: Activities from Trinidad (B)

Historic Trinidad Walk – 3 km, rated 1B
OPTIONAL Cubano National Park Walk – 4 km, rated 2B

Trinidad was probably our favorite place to explore in Cuba. The day is set aside to experience it in a number of ways. We start with a guided walk, enjoying several stops along the walk to delve deeper into the 500-year-old story of Trinidad. After a late-morning finish, the balance of the day is free. We strongly encourage travelers to allow time for unscripted strolling: musicians play spontaneously in many corners of the old town; shops and markets offer a plethora of colorful distractions; and quiet corners to sip a coffee and people watch abound. To give more structure to your afternoon and evening, the following options are also available:

  • A Salsa Dance Lesson ~ more details to come.
  • A walk through local neighborhoods to a local pottery shop run by five generations of Trinidad potters.
  • Cubano National Park Walk, with a chance to swim in a waterfall fed cavern.
  • Ancon Beach hang loose time on one of Cuba’s stunning Caribbean beaches.

Day 10: Trinidad – Havana (BD)

Valle de los Ingenios, or the Valley of the Sugar Mills, is just east of Trinidad and was combined with Trinidad in UNESCO’s 1988 World Heritage Listing. The valley is a living museum, with over 50 former sugar plantations, and provides tremendous insight into the dominant role that sugar, and by extension, slavery, has played in Cuba’s history and economy. Further north, a stop in Santa Clara at the Che Guevara Mausoleum introduces us to the life and times of perhaps the most revered of Cuba’s revolutionary leaders. Argentinian by birth, medical doctor by profession, and Marxist revolutionary in his political views, Che’s image has become a nearly universal symbol of countercultural rebellion in popular culture, and is one more key to understanding the Cuban conundrum. We finish the day back in Havana, looking forward to a farewell dinner and one final time to share and reminisce.

Day 11: Depart Cuba (B)

We return home from Havana today with much to ponder. What a special opportunity to connect with a culture that has been virtually off-limits to Americans for nearly 60 years! We return home enriched and encouraged to learn more about this fascinating island at the junction of the Atlantic Ocean and the Caribbean Sea, of North America and Latin America, and of Capitalism and Communism.

More Details

Click on each heading for more details.

How do I lock in my place on this Adventure?

Call or mail in your refundable Early Bird ($50) to save your spot! We will take an average of 24-28 travelers per departure. Each group will be accompanied by 2 Walking Adventures Guides and a local guide, offering a guide to traveler ratio of 1:9.

Early Bird deposits are refundable $50 deposits which serve to hold your spot on a tour until dates and pricing have been confirmed. Once all details on a tour have been finalized, travelers can then register with an additional $450 deposit to bring their total on a tour up to $500.

Traveler Rewards Program

New Travelers receive a $300 discount on the Colorful Cuba tour! Returning travelers receive our Alumni Traveler Discount of 5-10% off the main tour price. Terms, exclusions and conditions apply. See the Traveler Rewards page for more details or contact us with any questions at 800.779.0353 or [email protected].

How is Airfare Arranged?

Travelers will fly into and out of Havana, Cuba. More details on airfare and travel agent recommendations will be provided after this tour has been finalized.

What about the walks?

We generally walk at a pace of 2 to 3 miles per hour. In most cases, we are not “strolling.” We are walking at a relaxed but steady pace. Your experience will be significantly affected by your level of physical fitness. If not walking regularly at home, we strongly recommend that you make a priority of “training” beforehand in order to both enjoy the trip and avoid medical issues due to overexertion. If you have questions about your ability to participate, please talk with our office at 1.800.779.0353.

We have adopted a walk difficulty rating system, which contains a numeric indicator for trail incline and an alpha indicator for trail terrain.  The explanation for this system is presented below.


1. Very small hills or very little stair climbing. Cumulative elevation gain from Starting Point: up to 200 feet.
2. Some moderate hills and stair climbing. Cumulative elevation gain from Starting Point: 200-1000 feet.
3. Some significant hill or stair climbing. Cumulative elevation gain from Starting Point: 1000-2000 feet.
4. Lots of significant hills or stair climbing. Cumulative elevation gain from Starting Point: 2000-3500 feet.
5. Many steep hills. Cumulative elevation gain from Starting Point: more than 3500 feet.


A. Almost entirely on pavement.
B. A significant part of the route is on well-groomed trails with very few obstacles.
C. A significant part of the route is on somewhat difficult terrain (rocky / rooted paths or soft sand).
D. A significant part of the route is on very difficult terrain.
E. The majority of the route is on very difficult terrain.

What happens next?

Once the Cuba itinerary is released, we will accept registration deposits ($500) to save space.

If you have Early Birded with a refundable $50 deposit, your spot on the tour will be held for 2 weeks after the itinerary is published while you make a decision on whether or not you’d like to register with an additional $450 to bring your deposit on tour up to $500. If you decide not to join us for this tour, your Early Bird can be refunded or transferred to another tour.

We look forward to sharing Colorful Cuba with you!