Current Offers - Classic Cars, Rum, and Cigars

Please send me more info and current offers for your Classic Cars, Rum, and Cigars.

Guaranteed departures for 2 or more people! Please inquire today to begin the booking process.

Classic Cars, Rum & Cigars of Cuba

Step into Cuba’s most illustrious bars, drive around in timeless classic cars that take you back to another era, and indulge your senses with Cuba’s puros and libations. Follow in the footsteps of Hemingway, Sinatra, Gary Cooper, and Tennessee Williams. Sit in the Tropicana and imagine Nat “King” Cole singing into the hot Havana night. Sip on a daiquiri and see where Hemingway toiled away at his novels. Wander through tobacco farms where the world’s best cigars are produced and made - and then sit down and enjoy one.

Even though it’s been half a century since the glamourous days when Hollywood flew down in droves for weekends of dissipation and decadence, Cuba retains the air of flash and magnetism. Stepping into Havana can be like stepping into a self-indulgent novel or one of Frank Sinatra’s film sets. We invite you to experience Cuba’s indulgent side, its glamorous side, its uninhibited side. The side that enticed legends to its shores and then created them.

Experience classic, classy Cuba on our new Classic Cars, Rum, and Cigars tour. Don’t just read Cuba’s story - live it. Live it while learning richly from this Educational Exchange program, flooded with the knowledge of our teachers – cigar aficionados, rum connoisseurs and classic car enthusiasts. Designed for small groups of two to six people, and perfect for a private journey, this tour dives deep into Cuba’s history and pleasures.

*Note: this tour is available with THREE accommodation options: 1) Traditional Casa Particulares or 2) High-end Casa Particulares. 3) The Grand Aston Hotel in Havana.  Casas Particulares are private home accommodations similar to B&Bs in the United States, though some high-end casas can feel more like a boutique accommodation than guesthouse.

Images & Videos

classic blue car on a busy street at night in Cuba
woman standing with statue in Havana Cuba
Birds eye view of people eating at a restaurant in Cuba
hats on a wall
lobster on plate
man smoking a cigar
woman holding up drawing in havana cuba
group of people touring havana cuba
cuban cigar
person with drums resting on legs
colorful classic cars lined up on cuban street
classic blue car on a busy street at night in Cuba
woman standing with statue in Havana Cuba
Birds eye view of people eating at a restaurant in Cuba
hats on a wall
lobster on plate
man smoking a cigar
woman holding up drawing in havana cuba
group of people touring havana cuba
cuban cigar
person with drums resting on legs
colorful classic cars lined up on cuban street


Collapse all days

Day 1

Havana Hotspots La Bodeguita del Medio, El Floridita, and Tropicana

“My mojito in La Bodeguita, My daiquiri in El Floridita”—Ernest Hemingway

This tour begins when you arrive at the airport, where your local guide and drivers will greet you and provide a brief orientation before you head out into Cuba’s most dynamic city. Our first stop: La Bodeguita del Medio, which may translate to the unassuming name of “the little bar in the middle of the block,” but the restaurant and bar is anything but bland. La Bodeguita’s claim to fame lies in being one of Hemingway’s endorsed haunts where he discovered the mojito. The bar now serves double rum portions for the “Double Papa”—Hemingway’s specialty serving that leaves little doubt for the writer’s love of rum. Although the restaurant has a framed piece of parchment blazoned with Hemingway’s seal of approval and signature, stepping into La Bodeguita means you’ll be swilling some rum where Hemingway wasn’t the only famous patron. Joe DiMaggio, Nat “King” Cole, Frank Sinatra, Marilyn Monroe, Francis Ford Copolla, Pablo Neruda, and Benny Moré also found their way here. The bar’s walls are slathered in autographs, centerfolds, and photographs—some from illustrious guests and some from simple passersby who want to make their mark.

After this welcoming cocktail, we stretch our legs with a walking tour of Habana Vieja stopping in the area for lunch. Colonial Havana’s colonnaded streets are as colorful as our cars. Walk through a rainbow of pastels to the Havana Club Rum Museum, where you will enjoy a guided tour to learn about the manufacturing process from field to bottle.

We will head to you accommodations for the night so that you can rest and prepare for a night out in the city. 

We pick you up in your classic car (or regular taxi if not available) and head out to one of Havana’s Paladares for a tasty dinner. Either before or after dinner, we’ll stop by another of Hemingway’s illustrious watering holes: El Floridita. Hemingway sat in a corner seat, drank daiquiris, and conceived then wrote For Whom the Bell Tolls there. Hemingway must have been a trend setter because the bar also saw visits from Ava Gardner, Tennessee Williams, Spencer Tracy, Jean-Paul Sartre, and Gary Cooper. Papa Hemingway remains their favorite, and his seat remains forever unoccupied and chained off. Hemingway drank here a lot and drank a lot here. Have a daiquiri and see if you feel some literary inspiration yourself.

We finish off our day of literature and libations with a trip to the legendary Tropicana. Set in the open Cuban sky, the decant night-club has retained the glamour and glitz over the years. Salsa shows and señorita showgirls survived the revolution and continue to set nights ablaze. Enjoy the performance and Havana’s most notorious nightlife spot before we return by taxi to our accommodations for the evening.

ACCOMMODATION : Casa Particulares or Hotel
MEALS INCLUDED : Lunch, Dinner

Day 2

Cojimar, Ernest Hemingway Museum, and Fábrica de Arte

Your guide picks you up in your Classic Car after breakfast to begin our day of all things Hemingway.  It’s a short drive east to the small fishing town of Cojimar, which inspired The Old Man and the Sea and saw frequent visits of Hemingway and his boat, Pilar. We walk through the town and stop at some of his favorite sundowner spots before joining our friends at El Ajiaco restaurant.  We visit the gardens where some of their vegetables and herbs are grown, then have a lesson in how to make a stunning mojito.  With our minds ablaze and stomachs prepped, we sit down for the best lunch in Cojimar.   

After lunch, we continue our exploration of Papa Hemingway’s Cuba as we make our way to his former estate at Finca Vigía and the recently renovated Museo de Ernest Hemingway. Hemingway lived in the Moorish-style home with his third wife, Martha Gellhorn, and wrote nine novels within its walls. Wander the rooms and the grounds of the estate and see where Hemingway lived his life as a man while writing novels that made him a legend.

After our tour, we return to Havana to visit a vintage car restoration garage. The garage brings nostalgia-laden classic cars back to their original comfort and elegance so that all guests can have the opportunity to travel back in time.

We return to our accommodations for a brief rest and for a chance to prepare for another fun-filled night in Havana.

We let the classic cars rest for the night and use regular Cuban taxi’s for an authentic experience. We pick you up from your accommodations and we are off to enjoy an authentic Cuban meal at one of Havana’s finest paladars before hitting the town for a night out. While the Tropicana might be Havana’s most iconic nightclub, the Fábrica de Arte Cubano is its most entrepreneurial. Not just a nightclub, Fábrica de Arte teems with artists and musicians who don’t simply entertain but press the boundaries of Cuban culture. Take in the sights, mix and converse with the locals, and move to the beat in this stunning performance space before returning to our accommodations for the evening. 

ACCOMMODATION : Casa Particulares or Hotel
MEALS INCLUDED : Breakfast, Lunch, Dinner

Day 3

Valley de Vinales

Boisterous Havana recedes into the bucolic countryside as we drive west in classic style, into one of Cuba’s most stunning landscapes: Valley de Viñales.

Surrounded by the pine-clad hills of the Sierra de los Órganos, Valley de Viñales is a fantastical sprawl of lush green grass and limestone mogotes that rise precipitously from the hallowed ground. A maze of caves curve through the mountains and defined paths are a rare luxury in Cuba’s create-your-own-adventure playground. We explore the hidden sights of the valley flecked with tobacco farms before we head to a nearby organic farm for lunch.

Meet with the people who tend the land, learn about organic agriculture in Cuba and sample their fresh, carefully cultivated produce. After visiting the valley and learning about how the tobacco farmers (vegueros) grow and process their production, in the afternoon we will drive through town to visit a plant where the tobacco leaves bought by the government go through a bigger scale industrial process before being sent to aging and then to the Cigar Factories.

We head to our accommodations for the night and we dine at one of the town's fine Paladars.

ACCOMMODATION : Casa Particulares
MEALS INCLUDED : Breakfast, Lunch, Dinner

Day 4

To Havana

After breakfast our adventure continues as we cruise in style to Havana and enjoy the panorama on the way. We return to Habana Vieja’s cobbled streets and head to the Mercado San José. This crafts fair has a palpable soul with its handcrafted goods, colorful stalls, and cheerful vendors. It also features theatrical performances and art exhibitions—transforming the space from a market to a cultural center. It’s the perfect place to visit on our last full day on the island if you’re hoping to take a piece of Cuba with you!

After we drop off our souvenirs at our accommodations, we celebrate our final evening together in Cuba with a farewell dinner that features the best of Cuban dishes. Take a page from Hemingway’s book and sit down with a mojito or daiquiri Papa Hemingway style.

ACCOMMODATION : Casa Particulares or Hotel
MEALS INCLUDED : Breakfast, Lunch, Dinner

Day 5

Museum of Fine Arts and Adios Havana!

If flight schedule allows time this morning, we visit the Museum of Fine Arts in central Havana (Museo Nacional de Bellas Artes de La Habana).  This fabulous museum has two impressive buildings.  One is dedicated to Cuban art and includes a wide range of subjects and styles.  The other is a divine European masters collection including originals by Goya, Murillo, Velasquez, Gainsborough, Rubens and various impressionists. The museum also houses one of the most important collections of Greek and Roman art in Latin America.
You also have the option of traveling to Miramar to visit La Casa del Habano—considered one of Cuba’s finest cigar stores. Tour the picturesque store and hopefully get a chance to talk to Carlos Robaina, son of Cuba’s Godfather of cigars. Sip on a Cuban coffee served on tobacco leaves while trying out some aromatic products before heading to the airport. 
Once done, we make our way to the airport to catch your return flight home.  Today’s transport is done by regular taxi.

As required by U.S. law, we have a full-time agenda of people-to-people activities.  Cuba has it’s own beat and things don’t always run on time. The activities and visits listed are not guaranteed but we endeavor to do our best to provide the content intent of this people–to-people program.  Visiting developing countries can be eye-opening and life-changing, and hopefully visiting Cuba is both. Accommodations may not be up to the standards you are used to.  Sometimes the hot water or air conditioning doesn’t work.  We ask all our guests to appreciate the authenticity of your cultural encounters as well as the people, food, culture, and adventures that are exceptional in their difference.  Our local guide, along with your Cuba Unbound Tour Leader promise to do their best to make this a fascinating and educational experience.


Dates & Rates

DatesAdult (USD)Child (USD)
Jan 01, 2024 to Dec 31, 2024
Lowest Tier Price, Details Below

Supplementary Information

Dates: Guaranteed departures for 2 or more people on any Saturday or Sunday! Please inquire today to begin the booking process.

Rates (all prices below are per person in USD)

Standard Casas Particulares:

  • 2 guests (1 car) - $2,245
  • 3 guests (1 car) - $2,045
  • 4 guests (2 cars) - $2,145
  • 5 guests (2 cars) - $1,945
  • 6 guests (2 cars) - $1,845
  • 6 guests (3 cars) - $2,045

High End Casas Particulares:

  • Please inquire for specific pricing.

Group Size: This trip is perfect for one or two couples traveling in one car, but we can group several cars together if you have a larger group. Because you will also have a guide and a driver with you, two couples per car is the absolute maximum and you would likely be more comfortable with just one couple per car.

*Note on seat belts: Please note that the classic cars in Cuba do not have seat belts. If you are not willing to accept the risk involved in traveling without a seat belt, then we can also arrange this tour in a modern taxi that does have seat  belts.


  • Experienced English-speaking guide(s)
  • Specialized activity guides based on activity of trip (kayaking, biking, hiking, etc.)
  • Specialized equipment needed for activities such as kayaks, bikes, helmets, paddles, personal flotation devices, etc.
  • Private pre-tour orientation meeting
  • Cuba Unbound hand-crafted itineraries
  • Accommodations as noted in the itinerary
  • All meals as noted in itinerary
  • Certification of travel to Cuba under the U.S. Department of Treasury general license
  • Small group size (Custom tours for 2, group tours are 16-18)
  • All entrance fees to include events and activities
  • All in-country ground transportation
  • Clean drinking water available at all times
  • Gratuities for presenters, luggage handling, and restaurant staff
  • Cuba Visa (a $80-120 value)

Not Included: 

  • Round-trip air to/from Cuba 
  • Guide and driver gratuities 
  • Personal expenses such as souvenirs, gifts, alcoholic beverages, additional entertainment outside the standard itinerary, and incidentals


Average: 5 (1 vote)



Cuba. Bound. The Willoughby’s

Our Cuba trip was amazing. We were completely taken care of with an outstanding guide and drivers. We were shown old Havana, cigar factories; driven in a beautiful 1955 classic car and our trip to a nightclub was truly a fabulous end to a safe, once in a lifetime trip. We were exposed to Cuban history and our guide was so knowledgeable we came away from our experience having felt the true Havana. We hope to return again and will most definitely contact Cuba bound. We highly recommend Cuba bound for their extreme oversight and attention to every detail pertaining to our unforgettable trip to Havana.

Write a review

FAQ & More

Can US citizens travel to Cuba?

Yes, you can travel to Cuba as a US citizen! Although, the United States is the only country that restricts its citizens from traveling to Cuba for touristic reasons, however, the U.S. does allow travel to Cuba under one of 12 permitted travel categories. Of these categories, most of our travelers are traveling under either "Support for the Cuban People" or "Educational People-to-People" travel.  

For more information on Cuba travel entry requirements, please see here

What are Casas Particulares?

This is something you'll hear in Cuba a lot. A casa particular is a private accommodation or private homestay in Cuba, very similar to a bed and breakfast, although it can also take the form of vacation rental. On ROW's Cuba Unbound tours, you can expect to stay in a mix of casas particulares, making for a full and authentic visit to Cuba.

Do I have to travel with a group or can I go solo?

This tour is designed for a small group of 2-6 people. While we can accommodate a solo traveler, we unfortunately must charge the double occupancy rate.

Can I bring Cuban cigars home?

US Travelers: As of September 2020 it is not permitted to bring Cuban cigars or rum back to the United States.  This may change in the future, so check the U.S. State Department website for updates.

So how much do Cuban cigars cost?

For Cuban cigar pricing info, check out Cigar Aficionado

Can I bring Cuban rum home?

US Travelers: As of September 2020 it is not permitted to bring Cuban cigars or rum back to the United States.  This may change in the future, so check the U.S. State Department website for updates.

Is there free time?

There will be some free time between tours and meals.

Can I drink the Water in Cuba?

Generally it's best to drink filtered tap water or bottled water.  In an effort to reduce the use of single-use plastic, we encourage you to pack a wide-mouth water bottle with a filter built in.  There are many brands available.

Is ice safe to have in my drinks?

If you are getting a drink at a hotel bar, or other bar establishment, the ice is most likely made with filtered or bottled water, so should not cause any issues.

Can I eat salads in Cuba?

Cubans pride themselves on proper hygiene and food handling.  The restaurants we use on our tours are very good and eating any salads or raw vegetables that are served is fine.

Custom or Private

You love this itinerary but want to change it a bit to make it perfect for you?  Or, are you wanting to simply make it private?  Either way, we can do it!

Fill out this quick form to begin a custom or private adventure of a lifetime:

Back to top