Discover Cuba

♦ Start: Havana
♦ Finish: Havana

This itinerary has been designed to meet requirements set by the United States Department of the Treasury, Office of Foreign Assets Control (OFAC) to provide those who register as participants in our programs to visit Cuba legally for educational people-to-people interactions. Our itineraries provide a full-time schedule of people-to-people educational exchange activities designed to result in meaningful interactions between our travelers and individuals in Cuba. United States law requires that all participants in our programs adhere to the full-time schedule of people-to-people activities. You should be aware that you are not traveling to Cuba as a “tourist.” You will be traveling as part of a people-to-people educational exchange program and must participate in all activities of the program. 


Come with us to a place unlike any other. Our Discover Cuba tour will indulge all of your senses and is the best way to begin your love affair with this vibrant destination. Cuba’s rich history and culture will come to life over eight magical days, and we are quite sure that you won’t want to leave. Cuba is in a state of fascinating transition, and is ready to open itself up to the world like never before. Imagine yourself ambling along the cobblestoned streets of gorgeous Trinidad and discovering the magic of Havana. Another highlight is the achingly beautiful town of Viñales, where the air is fresh and sweet, filled with rich aroma of tobacco and pulsating Salsa beats. Even the noise of those stunning 1950’s cars will be music to your ears.


8 nights/ 9 days

Physical Rating


Trekking, kayaking, boating, culinary, caving

Places Visited

Havana, Vinales, Cienfuegos, Bay of Pigs, Trinidad, Valley of the Sugar Mills, Santa Clara


  • Rest your weary head at a Cuban Bed and Breakfast, known as a Casa Particular. Experience the warmth of Cuban hospitality by staying with a Cuban family, who will make you feel right at home.
  • Explore Havana on foot and in a classic car and attend the famous cannon ceremony at the La Cabana Fortress.
  • Buy some pottery to take home from the Casa Chichi pottery house of the Santander family, a UNESCO World Heritage Site.
  • Try out some sultry salsa steps and dance the night away at Casa de la Musica in Trinidad.
  • Explore vibrant Viñales – the home of Cuba’s tobacco production.
  • Visit a tobacco farm to learn about the cigar making process.
  • Visit the Valley of the Sugar Mills and go hiking along the Sierra del Escambray mountain range to a 62m waterfall cascading into cool swimming holes.
  • Take in the final resting place of the iconic Che Guevara.
  • Be amazed by the French inspired architecture of Cienfuegos.
  • Enjoy a live performance by Cuba’s most famous musicians, Buena Vista Social Club!

Is this trip right for you?

  • The guesthouses (Casas) we use are much nicer than your average Cuban dwelling but keep in mind that each and every room is unique. Regardless of where you stay, power cuts and breaks in hot water are sometimes unavoidable, as in any developing country.
  • Funds can be difficult to access in Cuba. If you’re traveling from the US, bring plenty of cash and if you’re traveling from other countries, bring multiple credit cards from several different banks just to be sure (non-US affiliated banks)
  • Luxuries such as air conditioning, and even toilet seats, are often scarce. Part of the experience here is learning to appreciate everyday Cuban resourcefulness.
  • Internet access can be hard to come by, and when it’s available it’s often unreliable and expensive. This is, on the other hand, a great opportunity to take a break from modern devices and have a true holiday.
  • Cuba is different, and that’s a big part of its allure. Things don’t always go according to plan, and many things don’t work the same way as back home. Patience and good humor will go a long way in this beautiful destination.


Bienvenido! Welcome to Cuba! You are free to arrive anytime and someone will be waiting for you at the airport for transfer to your hotel. Upon arrival, take some time to soak in the decaying beauty of Havana and the surreal feeling that you have entered a bygone era. You are visiting Cuba at a historic time, as the gates finally creak open to a country so long forbidden.

Havana grew from an obscure port to a bustling hub when gold and silver that was being pillaged by the Spanish from the New World was taken to Spain. While the ships gathered in growing numbers, the pirates were not far behind and the treasures resting in Cuba’s ports were attacked again and again by Dutch, English, and French pirates. The Spanish built fort after fort for protection, but the English eventually captured the territory. An economic boom followed due to the English lifting the Spanish trade restrictions. Spain eventually exchanged the Florida territory for the island, but these years left an indelible mark on the city and the country, and Havana is slowly restoring its beautiful colonial buildings.

Along the seafront of Havana, the Malecon, the strains of salsa waft from the rebooted sound systems of vintage Cadillacs and Buicks, and the facades of grandiose seafront buildings are being slowly resurrected. Admittedly, the restoration money hasn’t quite reached most of the rest of the city yet. Just west of Habana Vieja, the gritty working-class district of Centro Habana is a picture of ruined, rutted beauty, and the well-heeled districts of Vedado and Miramar, west again, are more peeling and faded than salubrious cousins in more solvent cities. Street life in Havana is key: on-the-ground socializing is the top Cuban past time, whether that’s domino playing, gossiping, or arguing loudly about baseball, so from the Havana belles to the beauteous buildings, there is always something to captivate and beguile.

At 9 pm, we will attend the famous cannon ceremony at the La Cabana Fortress, where soldiers dressed in 18th-century uniforms fire a cannon over Havana Bay. It is a historical reconstruction dating back to the colonial era. Back then, the cannon fire announced the official end of the day and the time to close the city gates for the night.


— Airport transfer (only applicable if you arrive on Day 1 of the tour)
— Canon Ceremony at La Cabana Fortress

Overnight at Casa Particular


Havana (B)

Havana’s Old City is one of the best preserved and was designated a World Heritage Site in 1982. The streets are lined with colonial architecture, 16th-century fortresses, and countless churches. After breakfast, our local guide will meet us at the hotel and take us on a walking tour of Old Havana. We’ll visit La Catedral San Cristobal de la Habana, described by the novelist Alejo Carpentier as ‘music set in stone’. You will also visit famous landmarks such as Revolution Square, Palacio de Los Marqueses de Aguas Claras (now a restaurant) and the Plaza de Armas, complete with a statue of Manuel de Cespedes, one of the leaders of the independence movement. There will be plenty of opportunities for photos and stops at good museums on the walking tour including Museo de la Revolucion and the Museo Nacional de Bellas Artes.

In the afternoon, end the day with a tour of greater Havana by Classic Car. There are currently an estimated 60,000 pre-­‐1960 American cars hurtling through Cuba today and before the embargo, there were at least 150,000. Buicks, Chevys, and countless other cool-­‐finned cruisers rumble down the crumbling streets of Havana, many abandoned by their American owners when they fled in 1959 and kept going by Cuban ingenuity. This iconic mode of transport is the perfect way to see wider Havana and a very different side of the city. Here you will be chauffeured around some of the most famous areas of Havana including New Havana, Old Havana, the affluent neighborhood of Miramar and the famous cemetery of Colon.

Tonight, we’ll explore one of the many paladars for dinner (not included). For those looking to hit the town, consider a visit to the local’s favorite meeting-place where the best of the island’s avant-garde can be enjoyed. The Fabrica de Arte Cubano (F.A.C. – Cuban Art Factory) is designed for people to show up and consume art, whether it be cinema, music, dance, theater, visual arts, literature, photography, fashion, graphic design, or architecture. Space was the former headquarters for Havana’s electricity company, then converted to an olive oil factory, and is now an incredible multi-room space that truly captures the spirit of Cuba’s youth population today, giving us insight into what tomorrow might look like.


— Old Havana Walking Tour
— Classic Car Havana Tour
— Meals: Breakfast

Overnight at Casa Particular


Trinidad (B)

Today, we’ll depart Havana for our long drive to Trinidad… a favorite of many travelers to Cuba!  Trinidad was founded in 1514 by Diego Velázquez and is considered a jewel in Cuban colonial architecture. For some, Trinidad is a living museum, stuck in the time of Cuba’s first War of Independence when local sugar plantations were devastated by fire. The vibrant colors and soulful music littered along cobbled streets will simply take your breath away.

Once arriving in Trinidad, enjoy a cultural walking tour of the city. This beautiful colonial city is home to numerous churches and many beautiful buildings. Built on huge sugar fortunes amassed in the adjacent Valle de Los Ingenios during the early 19th century, the riches of Trinidad’s pre-war of independence hey-day are still very much in evidence in illustrious colonial-­style mansions bedecked with Italian frescoes, Wedgwood china, and French chandeliers. Declared a World Heritage Site by UNESCO in 1988, the town retains a quiet, almost soporific air in its rambling cobbled streets replete with leather-faced guajiros (country folk), snorting donkeys, and melodic, guitar-­wielding troubadours.

In the afternoon, we’ll learn about the cultural and social importance that dancing has to Cuba as we enjoy a Cuban salsa dance class with a local teacher. Cuban salsa (both the dancing & music) first came out of Cuba in the 1970’s and varies in style from Puerto-Rican, Miami, New York, Columbian, or any of the other varieties of salsa dance. Learn the steps and later this evening, you can practice at Casa de la Musica. Every night the area beside the Cathedral in Plaza Mayor come alive with a live salsa band! The music and the atmosphere is great, mojitos are cheap, and what’s more, you get one of the most beautiful starry skies thrown in for nothing.


— Private bus transportation from Havana to Trinidad (5 hours)
— Walking tour of Trinidad
— Salsa Dance Lesson & entry into Casa de la Musica
— Meals: Breakfast

Overnight at Casa Particular


Trinidad (B)

The first sound in the morning is the clip­‐clop of horse’s hooves on the cobbled streets followed by the cries of old men selling bread from bicycles (El pan! El pan!). Open your eyes, gaze up at the high wooden louvers of your 200-­year-‐old colonial room, and try to convince yourself you’re still living in the 21st century. Trinidad is one-of‐a-­kind, a perfectly preserved Spanish colonial settlement where the clocks stopped ticking in 1850 and apart from the tourists, have yet to restart.

We’ll start our day hiking the purple-­hued shadows of the Sierra del Escambray (Escambray Mountains). The high, cool mountains shelter coffee bushes, tropical birds, palms, and waterfalls. The most popular hike is the 2.5km, 2 ½ hour round-­trip trek to the Salto del Caburní, a 62m waterfall cascading into cool swimming holes (be sure to bring your swimsuit!).

Afterward, we’ll return to Trinidad and visit the Casa Chichi pottery house of the Santander family. This prestigious family in the Cuban cultural landscape has been making pottery for generations as well as assisting in the restoration of sculptures that once existed in this UNESCO World Heritage Site. Here, you will have a chance to purchase your own pottery to remind you of your time in Cuba.

In the afternoon, we’ll relax on the white sand beaches of Playa Ancon, located just twelve kilometers to the south of Trinidad and considered the south coast’s best beach. This precious ribbon of white beach on Sancti Spíritus’ iridescent Caribbean shoreline, is usually touted – with good reason – to be the finest arc of sand on Cuba’s south coast.


— Hiking in Escambray Mountains
— Visit the Casa Chichi Pottery House of the Santander Family (UNESCO World Heritage Site)
— Visit Playa Ancon
— Meals: Breakfast

Overnight at Casa Particular


Cienfuegos (via Santa Clara) (B)

Today we head to Cienfuegos. If Cuba had a Paris then it would be Cienfuegos, which stands out for its rich French-influenced architecture. “Cienfuegos is the city I like the best”, wrote Beni More, one of Cuba’s most important musicians in the first half of the 20th century, and we understand why. A harbor city by location, the ‘Pearl of the Caribbean’ has seduced Cuban travelers for years due to its elegance and beauty. Founded in 1819 by Don Luis de Clouet, Cienfuegos luckily managed to remain free of pirate attacks, allowing this popular city to prosper. Like Havana, it has a beautiful Malecon, and it has a distinctly European flavor, with a wide Parisian-style boulevard and elegant colonnades.

On the way, we’ll make a stop at the Valle de Los Ingenios (Valley of the Sugarmills), where the ruins of dozens of ingenios (small 19th-century sugar mills), including slave quarters and manor houses, are scattered throughout this valley. The royal palms, waving cane and rolling hills are timelessly beautiful. The prime site is Manaca Iznaga, an estate purchased in 1795 by the dastardly Pedro Iznaga, who became rich by trafficking in slaves. A 44m tower was built to look over the slaves as they worked. It has a sugar cane press that the slaves used to operate. The village around the mansion is inhabited by direct descendants of the slaves.

Next, we’ll stop in Santa Clara, which was the site of the last battle in the Cuban Revolution in 1958, and there are many tributes to the city’s troubled history here. You’ll have the opportunity to visit the Che Guevara mausoleum and memorial, where the mortal remains of this Cuban revolutionary are interred. You will learn about how Guevara played a pivotal role in the demise of the dictator Batista and the rise of Fidel Castro, a turning point in the Cuban revolution.

On arrival to Cienfuegos, we’ll settle into our casa before taking a walk around the city as you take in the grand, crumbling architecture and learn about its history. We’ll visit Parque Jose Marti and The Palacia del Valle, before enjoying a walk along the Malecon, where you can spend a peaceful evening watching fishermen cast nets and locals socialize.


— Private bus transportation from Trinidad to Cienfuegos (3 hours)
— Visit ruins in the Valley of the Sugar Mills
–­- Visit Che Guevara Memorial in Santa Clara
— Cienfuegos Walking Tour & visit the Palacia del Valle
— Meals: Breakfast

Overnight at Casa Particular


Havana (via Bay of Pigs) (B)

Today, we’ll have an early morning departure for our return to Havana. We’ll drive along the picturesque Playa Giron, also known as the Bay of Pigs. The infamous Bay of Pigs is the site where the landing of US-sponsored counter-revolutionary exile militia occurred in 1961. Today, there is a museum here that recounts the events of this conflict which resulted in the first defeat of a US-backed take-over in Latin America.

We’ll spend a bit of time here to go for a swim and to visit the local museum, so be sure to keep your swimwear & snorkel gear handy (or you can rent it there). One spot includes a sinkhole which resembles a huge natural tropical fish tank!

Afterward, we’ll continue our drive back to Havana, where we’ll spend the night.


— Private bus transportation from Cienfuegos to Havana (5 hours)
— Visit Bay of Pigs and the local museum
— Snorkeling at the Bay of Pigs
— Meals: Breakfast

Overnight at Casa Particular


Vinales (via Las Terrazas) (B, D)

Today, we’ll head east to a local community in Las Terrazas before continuing our journey to Viñales. Las Terrazas is a village built as part of a government reforestation project and has since received a UNESCO biosphere listing. Meet up with local community leaders who will share with us some insight into Las Terrazas and how society works. We will also visit the ecological research center and take a local guided walk around the Las Terrazas complex.

Afterward, we continue to Viñales – situated in a beautiful, lush valley of the Pinar del Rio province, Viñales is one of the most breathtaking and picturesque places in Cuba. In the heart of Cuba’s prime tobacco growing region, Viñales sits quietly surrounded by a number of stunning limestone pincushion hills known as “mogotes.”  The moment you spot a cigar-chewing guajiro driving his oxen and plow through a rust-­colored tobacco field, you know that you must be within striking distance of Viñales. This is a slow, relaxed, wonderfully traditional settlement that occupies one of Cuba’s most beautiful natural corners.

Viñales is one of the more agriculturally productive areas of Cuba, so an abundance of local seasonal fruit and vegetables are always available. After arriving and settling in for a bit, our guide will lead us on an orientation walk of this small and culturally rich village, with its friendly and welcoming residents. This evening, we’ll tour an organic farm and learn about sustainable farming in Cuba. We’ll meet a local farmer and learn about the methods used to cultivate crops without the use of pesticides. With the beautiful sunset as our backdrop, we’ll enjoy a deliciously fresh and diverse meal prepared by the family, a truly authentic farm-to-fork experience!


— Private bus transportation from Havana to Vinales (3 hours)
-— Visit Las Terrazas complex to learn about Sustainable Rural Economy Project
— Viñales Walking Tour
-— Visit an Organic Farm
-— Meals: Breakfast & Dinner

Overnight at Casa Particular


Vinales (B, D)

This morning, we’ll take a boat ride through a 400m underground river in the Cueva del Indio Cave and we’ll make a stop at Palenque de Los Cimarrones where you’ll learn about the Afro-Cuban religion and the history of the slaves in the 19th century.  It recreates one of the nomadic homes set up by the runaway slaves (cimarrones) that hid in the caves of the area.

Afterward, we’ll visit the Mural de la Prehistoria, a 120km long painting designed in 1961 by Leovigildo Gonzalez Morillo, a follower of Mexica artist Diego Rivera. On a cliff at the foot of the 617m high Sierra de Vinales, the highest portion of the Sierra de Los Organos, this massive mural took 18 people four years to complete.

We’ll also visit a local tobacco farm where we’ll learn about the tradition of Cuban cigars from a farmer and expert cigar maker. We’ll also see a fully operating secadero (drying house) in which tobacco leaves are cured from February to May.  Get an insight as to how the communist system works when you hear from the farmer. How much tobacco they keep and how much they give back to the government. You will learn about the process of tobacco planting to rolling the final cigar. Of course, you’ll get to try one as well!

This afternoon, we’ll make our way back to Havana and we’ll have our final dinner while watching Buena Vista Social Club live! The original Buena Vista Social Club was a members’ club in Havana that held dances and musical activities, becoming a popular location for musicians to meet and play during the 1940’s. In the 1990’s, nearly 50 years after the club was closed, it inspired a recording by Cuban musician Juan de Marcos Gonzalez and American Guitarist Ry Cooder with traditional Cuban musicians, some of which were veterans who had performed at the club during the height of its popularity. The recording, named Buena Vista Social Club after the Havana institution, became an international success, and the ensemble was encouraged to perform with a full line-up. In July 1998, German director Wim Wenders captured their performance on film, along with interviews with the musicians, and it was released on June 4, 1999, to critical acclaim. It received an Academy Award nomination for Best Documentary feature and won numerous accolades. The success of both the album and film sparked a revival of international interest in traditional Cuban music.


— Visit Indian Caves & Mural de la Prehistoria
–­- Visit a tobacco farm and drying house
— Private bus transportation back to Havana (3 hours)
— Final Dinner/ Buena Vista Social Club (live musical performance)
— Meals: Breakfast & Dinner

Overnight at Casa Particular


Havana/ Departure (B)

Today is departure day and there are no planned activities as we say goodbye to our guide and our new friends. At the appropriate time, a taxi will take you to the airport.


— Airport transfer
— Meals: Breakfast


December 15-23, 2018  USD $2295

Book Now

Tour price is per person (excluding flights) and is based on double/triple occupancy.

Due in Full by September 16, 2018
+ Single Supplement $220 (Optional)

Starts in Havana:  December 15, 2018
Ends in Havana: December 23, 2018

Trip Leader: Stacey

SIGN UP WITH NO RISK Your deposit is fully refundable or transferable

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Not Able to Join Us On Our Travel Club Trip? Grab a friend or more and go on the dates of your choice! 

8 nights Casa Particulars All meals indicated in the itinerary (B=Breakfast, L= Lunch, D=Dinner)
Bilingual, local guide Private transportation between destinations
Airport transfers for arrival and departure (Note: Complimentary transfers are only applicable if you arrive on Day 1 of the tour) Classic Car Havana Tour
Canon Ceremony at La Cabana Fortress Old Havana Walking Tour
Visit Las Terrazas complex to learn about Sustainable Rural Economy Project Viñales Walking Tour
Salsa Dance Lesson & entry into Casa de la Musica Hiking in the Escambray Mountains
Viñales Bike Tour (4-5 hours) Visit to a tobacco farm and drying house
Dinner at an Organic Farm Visit Bay of Pigs and the local museum
Cienfuegos Walking Tour & visit the Palacia del Valle Visit Che Guevara Memorial in Santa Clara
Walking tour of Trinidad Salsa Dance Lesson & entry into Casa de la Musica
Hiking in the Escambray Mountains Visit to Playa Ancon
Visit ruins in the Valley of the Sugar Mills Visit the Casa Chichi Pottery House of the Santender Family (UNESCO World Heritage Site)
Cooking Demonstration Final Dinner & Buena Vista Social Club Show
Airfare to/from Havana (HAV) Airport taxes & excess baggage fees
Travel Insurance Beverages & meals not specified
Personal Expenses Gratuities
Optional Activities  Cuba Tourist Card (Visa)
havana classic cars
casa de la trova
bay of pigs
Playa Ancon
buena vista social club
visiting a tobacco plantation
classic car
classic car tour
santa clara
tobacco farmer

Tour Reviews

5.00 based on 7 reviews
January 13, 2018

I leave it to Stacey to arrange all my far-flung adventures!

January 13, 2018

This was an excellent experience and certainly one we will never forget. The itinerary was packed with a great variety of activities, locations and scenery. Everyone was on board with really having an adventure and even though we had to push ourselves at times, it was well worth it in the end (I.e. climbing the tower in Valley of the Sugar Mills, long walk to the disco cave).

June 1, 2017

Stacey did a great job organizing everything. It was worry free. I just showed up. Plus, our local guide (Carlos) couldn’t have been more knowledgeable and friendly. And, the itinerary was a great mix of fun time, free time and historical sightseeing.

June 1, 2017

Trinidad was the most pleasant; the horseback riding was wonderful.

June 1, 2017

Our guide was so much fun! I learned so much from him and really enjoyed getting to know him and his country.

June 1, 2017

This was my second trip with Adventure People. The first was to Iceland! My favorite trip moment in Cuba was the tobacco Farm, horseback riding, lunch at the organic farm, riding in the classic cars, the Cigar Factory tour, and Trinidad.

June 1, 2017

Stacey is very organized, so as a traveler you can kick back and enjoy the experience w/o thinking and planning. Favorite trip moment? So many! The Classic car tour, Ziplining, bike riding in Vinales, and the Roof Top Dinner!

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