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Six Perfect Days in Cuba

Itinerary Overview

  • 5 nights in a Premium casa particular boutique hotel in Havana.
  • Private airport transfers with VIP assistance.
  • Unique and unforgettable cultural experiences daily with Cubans from all walks of life.
  • Full-service daily hosting by an English-speaking private guide and driver.
  • Full itinerary customization and restaurant reservations, as well as 24/7 in-country support.

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Legal Travel to Cuba

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 stay in privately-owned boutique hotels and dine 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.


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.

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. Although the colonial days are long gone, Old Havana is still home to one of the largest number of Spanish colonial buildings and therefore 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 at your casa particular or privately-owned boutique hotel, begin your exploration. 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 your English-speaking guide offering insightful history throughout. You’ll also learn about the social planning and challenges faced by residents in Old Havana, and have the chance to interact with locals working here.

Dinner reservation at one of our favorite privately-owned restaurants. After dinner, your guide will take you for a visit to the Fábrica de Arte Cubano (Cuban Art Factory), a huge, avant-garde space for art with a rotating collection of Cuban artists, as well as live music and several bars. (Open Thursday-Sunday evenings.)

Day 2

Exploring Havana

Take an 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 to the Cuban capital 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.�

After lunch (not included) at a great privately-owned restaurant, discover Cuba’s revolution history through some of the capital’s most historical sites including a stop (outside only) at the Revolution Museum, which was once the luxurious Presidential Palace of all Cuban presidents from Mario García Menocal to Fulgencio Batista. Discover with your guide how history then brought the country to the revolution led by Fidel Castro. Enjoy a panoramic trip through the Malecón where you will see the monuments of some of Cuba’s Independence War heroes. Finish this revolution experience in beauty with some city sightseeing at the Revolution Square a symbol of the Cuban socialist revolution.�-

Dinner reservation at one of our favorite privately-owned restaurants (paladars).  After dinner, explore Cuban music in one of the many new independently-owned venues for Cuban jazz, salsa and more.


Day 3

Further Exploration of Havana

This morning, 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. You’ll have a look around the grounds with your specialist guide, who can offer you fascinating insight into Hemingway’s life in Cuba.

On the way back to town, your guide will bring you to see Cojimar fishing village: a small picturesque town that inspired Hemingway to write the novel The Old Man and the Sea, and to whose fishermen he dedicated his Nobel Prize. As you finish the tour you will have an opportunity to see some of the most spectacular views of the city from the El Morro fort across the harbor from Havana. This tour takes approximately 4 hours and is typically done in convertible classic American car(s) from the 1950’s.

Then, you’ll have a lunch reservation (cost not included) at one of our favorite privately-owned restaurants.

After lunch, explore 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.

Or, if you prefer, explore Havana’s street art scene. The richness of art in Cuba spills out from museums and galleries onto the streets and public spaces. Our specialist guide will take you for a look at the most important government-sponsored and privately-produced public arts. From the barrio to the Revolution-sanctioned murals, but also many examples of the underground street art movement which can be provocative in dealing with current issues facing Cuba, you’ll get far off the regular tourist trail to see a slice of real life in Havana.

Day 4

Further Exploration of Havana

This morning, a foodie exploration of Havana including visits 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 also be added onto this activity, for an additional cost.

After free time for lunch (not included), experience some of Cuba’s iconic music and dance with a private salsa dancing lesson! Or, if you’d prefer, we can arrange for a special visit to one of the island’s top dance companies such as the National Ballet, Carlos Acosta Dance, etc.

Day 5

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 6

Until Next Time!

Morning check out and transfer to Havana airport for your flight back to the U.S. (Air not included.)

Looking to spend a few more days on this magical island? How about exploring the colonial charm and surrounding natural beauty of  Trinidad and Cienfuegos?  Our Taste of Cuba itinerary is a great starting point for a longer exploration of 8 days or more. Contact Exeter Latin America for more options.


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 in a Premium casa particular boutique hotel.
  • Breakfast daily.
  • Private arrival and departure transfers (assumes all guests on same flights.) English-speaking guide included when specified in itinerary.
  • VIP Airport service in Havana on arrival and departure.
  • Private, local English-speaking host guide for all transfers and activities, plus specialists for selected activities, as described in the program.
  • Visas.
  • Private air-conditioned classic car or van for all included activities and transfer, 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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