4 Nights in Havana Tour

Red vintage driving past colonial buildings in a tropical setting.

Image by Jenny Desmond

November 6-10, 2024.

Cost: $1795 (market value $2895); $1595 if you register by May 6th

Contact us for additional dates and availability.

At A Glance:

Always wanted to discover the sights and sounds of Havana, but don’t have much vacation time? This is for you! This tour has you at the airport on Wednesday morning and at home in your bed by Sunday night.

Join us for unique access to people and places the average tourist rarely sees. You’ll experience the best of Havana as well as a day outside the city in the mountains surrounding the Soroa Orchid Gardens and Las Terrazas UNESCO Reserve. Learn about Cuba from a local’s perspective, including live music, dancing, UNESCO World Heritage sites, delicious food, fascinating architecture, and of course…classic cars. Come travel with us!

The Details:

  • $500 deposit secures your space. Early Bird registrations 6 months prior to departure (May 6, 2024) receive $200 discount. Save now!

  • Single rooms available for additional $250.

  • Airfare is for this trip is on your own, best prices tend to be 12-16 weeks prior to departure. We will send you recommendations; part of having a no-hassle experience!

Please note, we have a minimum of 4 participants for this tour. If you want a smaller, private tour, we can make special arrangements.

    • You’ll be accompanied by a Bilingual Cuban Guide the entire time

    • Travel licenses, mandatory Cuban health insurance and visas

    • 4 nights in Casa Particulares, Cuban Bed & Breakfasts. We have discovered the most comfortable lodging in Cuba is in these air-conditioned Casas, verses hotels which are government-owned and lacking in many amenities.

    • 10 meals, almost always at paladares. The paladares of Cuba are unique in that they are privately-owned restaurants where the staff takes great pride in their delicious meals and hospitality.

    • Private, air-conditioned ground transportation for the whole tour with our own driver

    • Purified water included and always available (bring your favorite water bottle for refills)

    • Curious About Cuba educational program (two 3-hour sessions of instruction provided before the trip, available online)

    • Airfare to/from the US

    • Trip Insurance

    • 1 meal (dinner)

    • Tips

Map of Havana with marked locations.

A look at where this tour goes


Group of cheerful tourists posing outdoors with tropical plants in the background.

Day 1: Welcome to Cuba!

Arrive in Havana.

We will be greeted at the airport by Roger, our Cuban guide. He’ll take us to our B&B accommodations (casa particulares) in Centro Habana. We will get a layout of the city along with first impressions of the architecture and lifestyle of the city dwellers. Evening arrivals may choose to settle into your casa to rest or join the group and go out for dinner.

Meals: Dinner

A vintage red Chevrolet parked beside a white building on a cobbled street.

Day 2: Havana

We start with a visit to Fusterlandia in the fishing village of Jaimanitas and the home of the famous artist Jose Fuster. Fuster has made his entire home, and much of the surrounding neighborhood, into an outdoor art gallery using tiles in mosaic forms.  A Havana driving tour in classic cars will take you to the forest of Havana, the famous Revolutionary Square and through the gorgeous historic embassy neighborhoods.

The activities will be followed by lunch and a walking tour of the gorgeous Old Havana City, including the Jewish Quarter. 

Dinner is on your own tonight, but nearby suggestions will be available. 

Meals: Breakfast, Lunch

Pink  orchids bathed in sunlight amidst garden greenery.

Day 3: Into the Countryside

Say goodbye to the big city as we head southwest into the countryside to see Soroa and Las Terrazas.

The Soroa Orchid Garden was started in the 1940’s extending over 7 acres of hilly terrain. A local guide will describe how the University of Pinar del Río maintains the garden and its 700+ species to study Cuban orchids, including the diseases that affect them and the best ways to reintroduce certain species into the wild.

Next, we’ll go to Las Terrazas for lunch and exploring. Las Terrazas is a UNESCO Biosphere Reserve site that was created in the 60s under Castro’s leadership to reforest the land with over 1 million trees built on terraces up the hillsides. The ruins of a 19th-century coffee plantation still exist here, and it is home to a self-sustaining ecovillage that has attracted talented artists whose workshops and studios are open to the public.

We’ll wrap up the day with a 1 1/2 hour drive back into Havana.

Wear your bug spray or long sleeves for this day of enjoying nature.

 Meals: Breakfast, Lunch, Dinner

Musician in white attire playing a trumpet, sitting in front of a green door with a Cuban flag.

Day 4: Havana

We will start the day off with a drive to Cojimar, the quiet fishing village where Hemingway docked his boat and was the inspiration for the town in The Old Man and the Sea.  Following that we will drive up to Hemingway’s mountaintop home, seeing his personal library, his elevated writing den where he and his cats would spend days on end, and more around his home. It is an excellent example of how many well-to-do Americans lived in Cuba in the 1940s and 1950s before the Revolution.

We will return to Havana for lunch at a paladar, followed by a tour of the Museum of the Revolution, a visit to a cigar factory and a sip at the Havana Club Rum Museum. 

We’ll go out for a special farewell dinner, followed by the option of heading to the Morro Fortress for the 9 pm cannon blast and soldiers in colonial uniforms. Up for even more?  Relish your last night in Havana by going dancing at one of our favorite rooftop spots.  

Meals: Breakfast, Lunch, Dinner

Four boys on cart smiling and waving goodbye outside a gray concrete house with barred windows.

Day 5: Departure

Head to the airport 2 hours prior to your flight home. Say goodbye to Roger and our driver as you head back to the U.S. We hope you come back soon!

Meals: Breakfast


We offer this tour on demand. If you’re interested in learning more about our upcoming dates or would like to book this as a private tour, please fill out this form or email Jenny at Jenny@vivemastours.com