8 nights/ 9 days
Havana to 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.

2017 Dates:February 18-26 SOLD OUT
May 27-June 4 $1995 ($320 Single Supplement)
Dec 30-Jan 7, 2018 $1995 ($320 Single Supplement)
Trip Leader(s):Carlos
Places Visited:Havana, Vinales, Cienfuegos, Trinidad, Santa Clara
Activities:Walking, Hiking, Biking, Dancing, Cultural
Group Size:Min. 6 Max. 12
Travel Style:Basic
Physical Rating:Easy

Ready to book? Please click the button below to BOOK THIS TRIP and submit your information along with a $500 deposit.  Your deposit is fully refundable for 72 hours and always transferable to any of our other trips, or we can hold it for a future trip.

Book This Trip Request Information


  • 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 – on a bicycle.
  • 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!

Day 1: Havana

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 9pm, 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

Day 2: 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. The 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

Day 3: Viñales (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 in 1971 and has since received a UNESCO biosphere listing. It is a pleasant settlement of white-painted houses and a long apartment block overlooking the lake of San Juan, which now houses and ecological research centre. There is a paladar, as well as craft workshops, and a museum which sometimes holds folk music sessions. Following the death in a car accident of the popular singer, Polo Montanez in 2002, his house was opened as a museum, run by his brother. Once a woodcutter, he rose to fame as a singer/songwriter with many hits in the three years before his death, touring Latin America and Europe.

Afterwards, 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 plough 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.

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 enjoy a traditional home cooked meal at our Casa Particular.


— Private bus transportation from Havana to Vinales (3 hours)
— Visit Las Terrazas complex
— Viñales Walking Tour
— Meals: Breakfast & Dinner

Overnight at Casa Particular

Day 4: Viñales (B, D)

This morning, we’ll explore Viñales by bicycle. The terrain through this lovely valley is level to gently rolling hills, with no extreme hills. The scenery is stunning and gets better the farther you go. 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 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!

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.  Here, there is a restaurant located inside a limestone cave. It recreates one of the nomadic homes set up by the runaway slaves (cimarrones) that hid in the caves of the area.

Viñales is one of the more agriculturally productive areas of Cuba, so an abundance of local seasonal fruit and vegetables are always available. In the afternoon, 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 learn to cook Cuban-style with a cooking demonstration. Afterwards, we can sit back, relax and enjoy the well-prepared meal while overlooking the rolling mountains of Viñales, a truly authentic farm-to-fork experience!


— Viñales Bike Tour (4-5 hours)
–­- Visit to a tobacco farm and drying house
–­- Cooking demonstration & visit to an organic farm
— Meals: Breakfast & Dinner

Overnight at Casa Particular

Day 5: Cienfuegos (via Bay of Pigs) (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.

After a lunch stop (not included), 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.

There are some beautiful places to stop for a swim along the way to Cienfuegos, so be sure to keep your swim wear & snorkel gear handy (or you can rent it there). One spot includes a sink hole which resembles a huge natural tropical fish tank!

On arrival to Cienfuegos, we’ll settle into our guesthouse 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 Havana to Cienfuegos (5 hours)
— Visit Bay of Pigs and the local museum
— Snorkeling at the Bay of Pigs
— Cienfuegos Walking Tour & visit the Palacia del Valle
— Meals: Breakfast

Overnight at Casa Particular

Day 6: Trinidad (via Santa Clara) (B)

Today, we’ll depart Cienfuegos for a short 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.

On the way, 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.

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 Cienfuegos to Trinidad (2 hours)
–­- Visit Che Guevara Memorial in Santa Clara
— Walking tour of Trinidad
— Salsa Dance Lesson & entry into Casa de la Musica
— Meals: Breakfast

Overnight at Casa Particular

Day 7: Trinidad (B, D)

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.

Afterwards, 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. Here, we’ll enjoy a beach barbecue as we watch the sunset.


— Hiking in Escambray Mountains
— Visit the Casa Chichi Pottery House of the Santender Family (UNESCO World Heritage Site)
— Visit to Playa Ancon & Beach Barbecue
— Meals: Breakfast & Dinner

Overnight at Casa Particular

Day 8: Havana (via Valley of the Sugarmills) (B, D)

Today, we’ll have an early morning departure for our return to Havana, but we’ll make a stop along the way 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 sight 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.

Tonight, 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.


— Private bus transportation from Trinidad to Havana (5 hours)
— Visit ruins in the Valley of the Sugar Mills
— Final Dinner/ Buena Vista Social Club Show
— Meals: Breakfast & Dinner

Overnight at Casa Particular

Day 9: Depart Havana (B)

Today is departure day and there are no planned activities as we say goodbye to our guide and our new friends and head back to the US.


— Airport transfer
— Meals: Breakfast

What’s Included?

Local, English and Spanish speaking guide
All meals indicated in the itinerary (B=Breakfast, L= Lunch, D=Dinner)
Accommodations (8-nights Casa Particulars)
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
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
Snorkeling at the Bay of Pigs
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

What’s Not Included?

International airfare to Havana + airfare to gateway city (if required)
Beverages & Meals not specified
Personal Expenses
Travel Insurance
Airport taxes and excess baggage fees
Cuba Tourist Card (Visa)

What is a Casa Particular? 

A casa particular is basically a private home that provides paid lodging (think Airbnb). This has been part of the “Cuba experience” since 1997 when the Cuba government started allowing residents to rent rooms in their houses to tourists. All of our accommodations promise to be comfortable, quality experiences chosen for their location and character.

Note: It is important to note that Cuba tends to be quite different to other areas of the world you may have traveled in. Buildings and infrastructure are generally old and may not have been maintained to the highest standard. Elevators, internet and A/C often break down, things happen very slowly and water pressure and hot water can be minimal. Cuba is an amazing place to visit but to fully enjoy and relax, western expectations should be left at home and your sense of adventure should be your guide.


Trip Length
8 nights/ 9 days
Travel Style
Physical Rating
Starting at $1995