Captivating Cuba

High Adventure Tour

Fall 2021 • 11 Days • Approx $3700-$3900

Join us in 2021 as we explore the city streets and nature trails of the Pearl of the Antilles!

This tour is not yet finalized. We are waiting to finalize our 2021 Schedule till Spring of 2021, and will send out an announcement at that time.

Cuba is an incredible experience—truly unlike anyplace we’ve ever been! Physically, the country is beautiful—lovely agricultural scenes, pristine forests, and colorful birdlife. But what makes Cuba unique is the rare opportunity to see inside a self-contradictory culture that is both Caribbean, with its relational, island-based, laid back way of life, and Communist, with the opposite emphasis on a controlled economy and society. Yet, Cuba, like many places on the planet, is beginning to change. Though currently a museum into the past, it is slowly modernizing… opening up to a market-based economy in phases. Now is a good time to see Cuba!


  • Viñales Valley – a UNESCO World Heritage Site, Viñales Valley is considered one of the most vibrant nature spots in Cuba, and is one of the major tobacco growing regions
  • Cienfuegos – also a UNESCO World Heritage Site, this city is nicknamed “The Pearl of the South” because of its French colonial-era buildings
  • Trinidad – Yet another 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.
  • Caribbean Coastal Vistas & National Parks – multiple walks are available in reserves and protected areas with opportunities to enjoy the clear, turquoise waters of the Caribbean.

This is a draft itinerary. Revisions will be made, and an updated itinerary with dates and pricing will be made available!


Pricing is based on double occupancy.

  • Airport to hotel group transfers on first 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 included
  • 2 optional walk routes available
  • Walking fees for those collecting IVV walking credit
  • WAI guide service throughout
  • Cultural & historical expertise of national guide throughout
  • Local guide assistance in several national parks and reserves
  • All tipping for national and local guides, coach drivers, and group meals
  • Pricing is based on double occupancy. A limited number of single rooms are available for a supplement. We also provide a roommate matching service.

Activities/Visits to:

  • Classic Car tour
  • San Carlos de la Cabaña Fortress
  • Fusterlandia
  • Soroa Orchid Garden
  • Viñales National Park
  • Viñales tobacco farm visit
  • Cenote swimming experience
  • Ciénaga de Zapata National Park
  • Museo Girón – Bay of Pigs
  • Palacio de Valle
  • Coffee farm lunch
  • Topes de Collantes National Park
  • Trinidad Architectural Museum
  • Valle de los Ingenios sugar mill visit
  • Che Guevara Mausoleum
  • More fun and educational stops than we can list!

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 tourist. Casa particulares are typically a higher value option than hotels, which are all government-owned hotels. 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

Approximately 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. The official start and finish point for this adventure is Havana, Cuba (airport code HAV).


Included. We use motorcoaches seating 40+.

Traveler Age

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


This is a draft itinerary. Revisions will be made, and an updated itinerary with dates and pricing will be made available!

Click on each day to reveal more details. (BLD) refers to meals included – Breakfast, Lunch and Dinner.

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 into the unspoiled natural wonders of this Caribbean island that seems to be working their way through a late-19th to mid-20th century time warp.

Optional Excursion: Malecon & More Havana Walk 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 that 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, it’s currently under renovation to serve as the new home for Cuba’s National Assembly. Optional Malecon & More Havana Walk: Price To Be Announced.

Later this evening, we join travelers arriving today 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 – 7 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 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. Our private guesthouses for the next two evenings allow us the delightful opportunity 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
Challenge Walk: 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 Girón 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 Parque 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 solitary 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)

Topes 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 the 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, a rich variety of vegetation, and more opportunities to enjoy Cuba’s aviary wealth. As we descend through Topes de Collantes to Trinidad, we take in some of the loveliest panoramas 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 – 2 km, rated 1B
OPTIONAL Cubano National Park Walk – 4 km, rated 2B

Trinidad was probably our favorite place to explore in Cuba when planning this adventure. Today is set aside to experience the town in a number of ways. We start with a guided walk, enjoying several stops along the way and delving 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; 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 (pricing to be announced where applicable):

  • Salsa Cubano, also known as Casino to distinguish it from other salsa styles, has been an integral part of the daily Cuban social scene and culture since the 1950s. Today is your chance to join us for a fun instructor-led lesson – come feel the rhythm of the music as you learn the steps and experience the joy and spontaneity of this vibrant form of dance.
  • Enjoy a walk through charmingly Cuban neighborhoods as we make our way to a local pottery shop run by five generations of Trinidad potters. Here we learn about the craft and tradition of forging clay from skilled artisans.
  • Join us for the Cubano National Park Walk, as we stroll along a lovely forest stream and keep our eyes open for colorful bird sightings. Our trail ends at an enchanting waterfall-fed cavern with the opportunity to take a quick dip, swimming right under the waterfall.
  • Ancón Beach – Enjoy some hang-loose time on the white sands of one of Cuba’s stunning Caribbean beaches! Just a 10-minute drive from Trinidad, it’s the perfect place for an afternoon of swimming, lounging and relaxation.

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 in the same hotel, 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 at leisure, with much to ponder. Cuba has challenged and delighted us. 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 fascinated by this island at the junction of the Atlantic Ocean and the Caribbean, North America and Latin America, Capitalism and Communism.

More Details

Click on each heading for more details.

How do I lock in my place on this Adventure?

We are not accepting deposits on our 2021 tours at this time. We are waiting to finalize our 2021 Schedule till the Spring of 2021, and will send out an announcement then.

How is Airfare arranged?

The official start and finish point for this adventure is Havana, Cuba (airport code HAV). More details about flight arrangements and travel agent contact information will be available after this tour has been finalized.

Guesthouses versus Hotels

  • Staying in private guesthouses is a unique aspect of a visit to Cuba. Hotels are owned and operated by the government. Guesthouses, or casa particulares, are privately owned, usually home-based, and generally open 1 to 4 rooms of their home for guests. This is a booming element of the tourism industry and Cuban economy.
  • One of our objectives is to structure the trip in such as way that most of the money we spend in Cuba is channeled to private individuals and businesses. Staying in guesthouses accomplishes this, and also avoids possible US government restrictions that have the same objective.
  • We plan to be in hotels for 4 nights and in private guesthouses for 6 nights.
  • You can expect your room to be clean; each room has its own private bathroom; all rooms should have air conditioning; some rooms will be on second or third floors but hosts are normally willing to help with luggage; breakfast is served in the home in which you stay and generally is lovingly prepared with lots of fresh fruit, baked goods, and an egg or two (which were in short supply when we visited). You won’t go hungry!

Visiting a developing country

  • Cuba is an enigma, to put it mildly. It is safe; crime is rare; gangs are not tolerated; drugs have a very low profile or are non-existent. Yet Cubans are accustomed to making do with much less than the average American. Expectations for life are remarkably simple.
  • What we would call poverty seems the norm and people use well-established support networks to live and cope. Varying degrees of this minimalist lifestyle will be visible and will impact us.
  • Expect to experience scenes of poverty, of overworked horses or draft animals, of conditions that seem blatantly unsafe, and other norms of Cuban lifestyle that would be stunningly out of place in the USA. One of the primary benefits of travel is seeing life through the eyes of a different culture and from differing points of view. This is exceedingly true of a trip in Cuba. Sometimes this can be uncomfortable. Usually it is thought-provoking.

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. Because these are guided group walks, the success of the walks is predicated upon walkers having this minimum level of fitness in order to ensure that we are walking at a somewhat similar pace. 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.

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.