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Havana, Viñales, Cienfuegos and Trinidad

An in-depth, people-to-people exchange with English-speaking guides, private transportation and unforgettable authentic experiences



Almaz Journeys operates private journeys to Cuba in compliance with the U.S. Department of Treasury’s general licenses for Cuba travel. Our custom journeys include the required full daily schedule of cultural exchanges, while still being tailored to your interests and giving you some flexibility. We use our favorite private sector guides, and you will generally dine only in our favorite privately-owned restaurants (paladares) – all to ensure you’re supporting Cuba’s burgeoning private sector as much as possible.

Throughout your stay, you will meet many Cubans from different professions, ages, and experiences in order to witness in-depth this period of profound change in Cuba and promote greater understanding between the U.S. and Cuba. Please note that this is not a tour, and under the general licenses you are required to participate in all activities on your schedule.


Arrival From the US

Welcome to Cuba!

Upon arrival this afternoon (flight not included), your local Almaz Journeys representative will meet you outside for your private arrival transfer.

Any trip to Cuba must begin with the majestic faded glory of Havana. Located on the northern coast of Cuba just 105 miles from the U.S., Havana was founded in the 16th century by the Spanish and quickly became a jewel in its New World holdings as a strategic trading stop between Spain and its colonies. The large number of Spanish colonial buildings in Old Havana are just one reason it is a UNESCO World Heritage site.

With investments in ongoing restoration since the 1990s, the faded facades of colonial buildings, the fountain-filled plazas, and the oceanfront promenade known as the malecón are all slowly returning to former glory. Havana (and Cuba overall) is one of the most exciting destinations in the world today, offering the chance to witness yet another period of change through the eyes of everyday Cubans.

After check-in, you’ll meet your Cuban guide and driver to begin your exploration with an afternoon overview drive around Havana including an essential stop at El Morro, the fortress at the mouth of the harbor, for panoramic views of the entire city. Your introduction this afternoon will take you along the seafront boulevard (malecón), to Revolution Square, and past important landmarks including the impressive Bacardi building and numerous former Mafia haunts including Meyer Lansky’s Havana Riviera Hotel.

Tonight begin your stay with one of our favorite long-running privately-owned restaurants (paladares) housed in a historic mansion. (Cost of dinner not included.)




After breakfast this morning, meet your guide to start your day by seeing one of Cuba’s most famous exports up close, with a visit to one of Havana’s oldest cigar factories! Here you'll learn all about the skills used by the experts to hand-roll those famous Montecristo and Cohiba cigars! You’ll then walk in the footsteps of Havana’s colonial past as you explore the four key squares of Old Havana, a UNESCO World Heritage site, with a local architect who will discuss with you the restoration work done to date as well as the ongoing challenges in preserving Havana's architectural heritage. (Please wear comfortable shoes for this walking tour!)

After lunch (not included), you’ll explore Hemingway’s Havana in a classic 1950s American convertible! Gertrude Stein once commented that Hemingway had a good nose for finding good places to live and eat, and his villa outside Havana proves her point quite well.

Hemingway’s house is perched on a hill, with a terrific view of Havana in the distance and surrounded by lush tropical vegetation, so it's no wonder that quite a few celebrities made their way here in the 1940s and 1950s. The house you find today is perfectly intact, just as the famed author left it in 1960 with his personal effects, his favorite fishing boat, and lots more. Your visit will be led by a local Hemingway historian and expert, who will show you around the grounds and engage in an exchange about the long history of links between American and Cuban writers and artists.

After the visit while heading back to Havana, you’ll want to stop at the picturesque Cojimar fishing village, the inspiration for Hemingway’s novel “The Old Man and the Sea” – so much so that he later dedicated his Nobel Prize to the village’s fisherman.


We suggest dinner at one of our favorite privately-owned tapas-style restaurants in Havana. (Cost of dinner not included.)




For foodies, this morning we suggest you visit some of Havana’s best local markets this morning with a specialist guide to learn about urban farming and innovative solutions to food supply issues in Cuba, as well as a deeper insight into food history. Your guide may give you a shopping challenge to understand firsthand the challenges faced by everyday Cubans.

Or, you may prefer to spend the morning exploring the thriving local arts scene with visits to the studios of several emerging or established artists. Every exploration is tailored for you, whether you have a very specific interest or simply wish to get a taste of Havana’s thriving artistic community. Please speak with your Almaz Journeys expert about what types of art and artists you’d like to include this morning.

For those interested in ballet, you won't want to miss a rehearsal of the national ballet company. Here you'll see the young emerging stars hard at work perfecting their craft and learn about the intense competition for a spot in the company. (Although photos are not officially permitted, you will be able to take a few discreet ones as reminders of your visit!)


Or, take the opportunity to learn about - and dance to –some of Cuba's celebrated music with a visit to a community-based rumba dance project. After a short introduction and lesson by the project leader in a private home, you'll continue on to a special venue to see firsthand where the community dance project is developed and, of course, talk and dance with the locals to Afro-Cuban rhythms.

For those interested in sports, a visit with your guide to a baseball game (in season) is a must to experience the sport that is far and away the most popular on the island. The season runs November-March, with playoffs often extending into May.


To close out your stay in Havana, we suggest an al fresco dinner on the roof of a former factory, located adjacent to one of the most exciting contemporary art spaces in Havana. After dinner, head next door to hear live music and see works by some of the island’s avant garde artists. (Cost of dinner and transportation for evening activities not included.)


Havana to Viñales


After breakfast, depart Havana early this morning toward the Pinar del Rio province and Viñales, set in a beautiful valley encircled by mountains and interspersed with dramatic limestone hills (mogotes). This is the heart of the tobacco-growing region of Cuba.

Upon arrival (approximately 2.5 hours later), your local guide will take you into the heart of the verdant countryside, explaining the history of tobacco growing as you walk. You'll visit the tobacco plantations where they still plow with oxen, see the famous drying houses and have a farmer show you how to roll a cigar. (There are numerous variations on this walk, and it can be tailored to your fitness level and interest. Exploring by horseback is also an option.)


Time and interest permitting, you may also explore some pre-colonial indigenous caves, and even take a dip in a lake before enjoying lunch in a traditional house overlooking the picturesque valley. Your hosts for lunch (included) have harvested and prepared your meal from their own farm (finca).

After lunch, you’ll continue on to Viñales and check in at a lovely privately-owned home (casa particular), hosted by a local family. You can count on clean, comfortable but simple accommodations always with air-conditioned bedroom and private en-suite bathrooms. Evening at leisure.

Tonight, we suggest dinner at one of our favorite private homes in Viñales. You’ll enjoy warm, friendly service and home-cooked food from a Cuban family. (Cost of dinner and evening activities not included.)



Viñales-Cienfuegos- Trinidad


Check-out this morning and depart toward Trinidad, with a stop in Cienfuegos. (Total driving time today approximately 6 hours.)

Located on Cuba's southern coast, Cienfuegos is another colonial gem whose historic city center is UNESCO World Heritage Site. Often called the Pearl of the South (la perla del sur), Cienfuegos was founded in 1819 on a spectacular bay and still retains a touch of the spirit of the French who first settled in this Spanish territory. As it was settled late for Cuba, the orderly layout of the city with wide streets and prominence of public spaces reflects the prevailing attitudes of urbanism and the Spanish Enlightenment. Some notable Neo-Classical architectural examples not to be missed include the Cathedral of the Immaculate Conception, the Tomas Terry Theater and the historic Union Hotel.

This waterfront city still has a relaxed feel, with horse-drawn carriages serving as a common form of transportation along the Paseo del Prado – Cuba’s longest street. Outside the historic center on the Punta Gorda peninsula, you’ll find an abundance of homes that remind many of 1950s suburban south Florida.


You’ll be charmed by the old fashioned beauty of many of the façades, such as the beautiful Cathedral of the Immaculate Conception. Another noteworthy stop is the Botanical Gardens, established just outside of town in the early 1900s by an American farmer. The Gardens are not heavily visited, so you may just find yourselves almost alone with your guide among than 2,000 species of tropical plants.

You will arrive in the early evening into Trinidad, where you will check-in at your private bed and breakfast (casa particular). Your local Almaz Journeys representative will welcome you and assist with any evening plans.

Tonight we suggest you have a walk around friendly Trinidad, and enjoy dinner in one of our favorite private restaurants near your casa. (Cost of dinner and evening activities not included.)




Trinidad is definitely one of our favorite towns in Cuba, and perhaps the island’s most beautiful with its pastel-colored houses and red tile roofs. Nestled between the foothills of Escambray mountains to the north and the Caribbean coast to the south, this 500-year old city is a UNESCO World Heritage site rich in Spanish colonial architecture built with the massive wealth generated by the sugar trade.

Unlike many other colonial gems in the Americas, however, Trinidad is not just a museum but a living town. Lots of locals live right in the historic center itself, so as you leave your casa particular in the morning to explore the cobblestone streets, be sure to say hello to the neighbors!

This morning, your guide will bring this UNESCO World Heritage city alive as you walk through the town past some of its architectural highlights, giving you some insight into its complex history both during the colonial period and post-revolution. Please wear comfortable shoes today!

After some free time for lunch (not included), you will head out of town to take a tour of the former sugar plantations, to understand the slave history and its central role in the development Cuba's sugar industry. Visit some of the old slave quarters to fully comprehend just how this system operated and the enormous impact the cultivation of sugar had on this region. You’ll also see working plantation homes of the sugar barons.

Late afternoon return to Trinidad and another evening at leisure to explore this colonial gem.


Trinidad and Topes de Collantes National Park


This morning, you’ll head for an unmissable visit to the lush national park Topes de Collantes, situated between Playa Giron and Trinidad.

It's a place of extraordinary beauty and of great value for Cuban scientists. This protected area of 77 square miles boasts a plethora of endemic species of flora and fauna–many of which your specialist guide is incredibly talented at spotting!

During the park visit, you’ll get to hike (varying distances and durations can be arranged, depending on your interest and aptitude) and even cool off with a swim near one of the three waterfalls in the national park! (Please note waterfall flow is much lower in the dry season.)



Upon return to Trinidad, you’ll have some more time to explore with your guide. Trinidad has a strong artistic tradition and its artists, while not as widely recognized as those from Havana, have made a reputation for themselves both nationally and internationally. If you are interested, we can organize a visit here with one of the most successful contemporary artists in the city.

After dinner tonight (not included), cap off your visit to Cuba with a stop at Casa de la Música, where live performances often fill the square with tourists and locals alike dancing together under the stars.


Return To The US


Check-out this very early this morning and transfer back to Havana for your return flight to the U.S. (Air not included.)

Please note if your flight will leave Cuba before 3 PM, we strongly recommend you return to Havana the night before your flight.

Tailoring Your Journey

This is just a brief sample visit to Cuba, which can be completely tailored to suit your needs and specific interests. Below are just a few of the countless possibilities that can be incorporated in customizing your journey to Cuba:

Drop in during a rehearsal of the Cuban National Ballet

Work up a sweat with private salsa dancing lessons

Dig deep into revolutionary Havana with a specialist guide

Explore former mafia haunts, some completely unchanged since the Revolution

Visit a classic car workshop to learn how Cubans keep them running

Private Journey Pricing

Starting pricing per person, based on double occupancy in deluxe casa particular (prices vary based on exact dates of travel, accommodations, and exact program of activities)

2 Guests Traveling Together
From USD $6,250 per person DBL

4 Guests Traveling Together
From USD $5,150 per person DBL

6 Guests Traveling Together
From USD $4,850 per person DBL


  • Accommodations in Havana for 3 nights in privately-owned deluxe casa particular. Upgraded accommodations available at an additional cost: boutique hotels, private villa, or Melia Cohiba - The Level.
  • Accommodations in Viñales for 1 night in one of our favorite private casas
  • Accommodations in Trinidad for 3 nights in one of our favorite privately-owned casa particulares. Upgrade to Iberostar Grand available at an additional cost.
  • Breakfast daily, and one lunch in Viñales
  • Private arrival and departure transfers with English-speaking driver-guide and VIP arrival assistance
  • Specialist local English-speaking guides for select exchanges and experiences
  • Best available air-conditioned vehicles with English-speaking driver-guide for all daytime sightseeing and dinner transfers (as needed), with bottled water. Evening transportation available at an additional cost
  • Entrances for all sights and experiences specifically included in your itinerary
  • Local concierge service to handle all dinner and evening reservations and 24/7 Emergency Contact.


  • Air travel
  • Lunches or dinners. We will assist you in selecting and reserving the best dining options, based on your needs and taking into account the rapidly change dining landscape in Cuba.
  • Gratuities
  • Medical or travel insurance. (Mandatory health insurance is typically included with the purchase of any flight between the U.S. and Cuba)
  • Any other items or services not specifically included in the itinerary

Excited to learn more?

Get in touch with us with us today to start planning!

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