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A Taste of Cuba

Itinerary Overview

  • 7 nights in deluxe casa particular boutique accommodations in Havana and Trinidad. Upgrade to Premium options available in Havana.
  • Private airport transfers with VIP service.
  • English-speaking private guides & driver for all included cultural activities.
  • Advance itinerary customization and restaurant reservations, as well as 24/7 in-country support.

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Exeter Latin America 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.

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.

Day 1

Welcome to Cuba!

Upon arrival this afternoon (flight not included), your local Exeter Latin America representative will meet you outside for your private arrival transfer to your accommodations – either a casa particular or a choice of privately-owned boutique hotels.

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 in a classic convertible car. 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, as well as an essential stop at El Morro, the fortress at the mouth of the harbor.

Tonight begin your stay with a dinner reservation at one of our favorite privately-owned restaurants (paladares), followed by a performance at the famous Tropicana. (Cost of dinner not included.)

Day 2

Exploration of Havana

After breakfast this morning, meet your guide to continue exploring Havana. You’ll then walk in the footsteps of the city’s colonial past as you explore the four key squares of Old Havana, a UNESCO World Heritage site. As you walk around, you’ll stop into one of the privately-owned shops or businesses to learn a bit about entrepreneurship in Cuba.  (For the Premium experience, you’ll be joined this morning by an architect who is well-versed in the restoration work done to date as well as the ongoing challenges in preserving Havana’s architectural heritage.)

After lunch (not included), you’ll explore Hemingway’s Havana. 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.

Dinner reservation again tonight at another top paladar. (Cost of dinner not included.)  After dinner, you’ll visit the Fabrica de Arte Cubano, a former cooking oil factory founded by one of Cuba’s most respected and revered Afro-Cuban fusion musicians, X-Alfonso. The space has been restored and now promotes local Cuban artists, writers, photographers, intellectual, filmmakers and performers.

Day 3

Further Exploration of Havana

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. (A cooking class can be incorporated into this activity, if you’d like.)

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 Exeter Latin America expert about what types of art and artists you’d like to include this morning.

Other options that you may wish to consider in customizing your itinerary with us (pricing varies):

  • Sit in on a rehearsal of one of Cuba’s top dance companies, and chat with dancers about their rigorous training and the importance of such cultural institutions in Cuba.
  • Meet with any number of entrepreneurs, such as the owner of a garage that restores and repairs classic cars or the director of a start-up consulting firm that advises small privately-owned Cuban businesses such as restaurants, cafés and B&Bs.
  • Learn about some of Cuba’s celebrated music with a visit to a community based rumba project
  • Explore Havana’s public and street art scene with a specialist guide, either by car or bicycle.
  • Spend a morning exploring mafia history or the Cuban Revolution with a specialist guide.

After some time for lunch, you’ll visit a private home in Old Havana for a private salsa lesson.  The owners of the house are professional instructors and, after a brief introduction, will have even those with two left feet up and dancing in no time!  If you’re really into dancing, we suggest later this afternoon you visit a salsa matinee – a truly local experience where you’ll be able to meet and dance with an almost entirely Cuban crowd!  This is a fun way to get some dancing in before a later dinner, for those who like to get to bed at a reasonable hour.

Dinner reservation at another of our favorite privately-owned restaurants in Havana. (Cost of dinner not included.)

Day 4

Day Trip to Viñales

After breakfast, depart Havana 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). This is real Cuba, nothing fancy –  just great Cuban home cooking, a chance to relax with warm and welcoming people, and a learning experience about Cuban rural life in possibly the most beautiful destination in Cuba.

After lunch, you’ll depart back to Havana with your guide. We’ll make a dinner reservation for you again this evening at a paladar.

Day 5

Journey to Trinidad via Cienfuegos

Check-out this morning and depart toward Trinidad, with a stop in Cienfuegos. (Total driving time today approximately 4 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. 

You will arrive late afternoon into Trinidad, where you will check-in at your accommodations.

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

Day 6

Exploration of Trinidad

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 visit the former sugar plantations, to understand the slave history and its central role in the development Cuba’s sugar industry.

In addition, you will meet with teachers from local school, some of whom will travel down from extremely rural schools to meet you and talk about education and rural Cuban living. While education is free and available for all in Cuba, resources are lacking so would be a perfect opportunity to share donations such as over-the-counter medicines, clothes and school supplies.

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

Day 7

Further Exploration of Trinidad & Surrounding Areas

After checking out from your casa or hotel, 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.)

After a picnic lunch (included), you’ll depart with your guide and driver back to Havana.

On arrival back into Havana, check back into your casa or boutique hotel. We’ll again make a reservation for you at a favorite paladar for your final dinner in Cuba. (Cost of dinner not included.)

Day 8

Until Next Time!

After breakfast, check out of your casa or hotel for private transfer to the airport for your return flight to the U.S. (Premium experience includes VIP airport service today.)

(If you have a later flight, your program can be customized to include additional time to explore with driver and guide – additional costs apply.)

Private Journey PricingPer Person

Pricing Level
From Price Per Person
Deluxe Itinerary: 2 Guests Traveling Together


Deluxe Itinerary: 4 Guests Traveling Together



  • 5 nights in Havana: Deluxe Casa particular, with optional upgrade to Premium casa particular.
  • 2 nights in Trinidad: Deluxe Casa particular.
  • Breakfast daily.
  • Lunch on days 4 and 6.
  • Private arrival and departure transfers (assumes all guests on same flights.) English-speaking guide included when specified in itinerary.
  • VIP Airport service in Havana (arrival and departure).
  • Private, local English-speaking host guide for all transfers and activities (supplemented by expert guides for Premium experience) as described in the program.
  • Visas.
  • Private air-conditioned prepaid taxi (modern rental vehicle for Premium experience) for all included activities and transfers, with bottled water daily.
  • Round-trip transfers for dinners and included evening performances.
  • Cost of entrance for all sights and experiences specifically included in your program.
  • Local concierge service to assist with any special requests before and during your journey.
  • 24/7 local emergency contact during your journey.
  • Full-service advance tailoring of your itinerary and assistance with restaurant reservations.

Not Included

  • Air travel.
  • Lunches, dinners and alcoholic beverages unless otherwise specified in your program.
  • Gratuities to guides, drivers, hotel porters, etc. unless otherwise specified in your program.
  • Travel or medical evacuation insurance.
  • Any other items or services not specifically included in your itinerary.

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