8 Days


Only a short distance off the coast of Florida, but a world of difference from the USA.  The small island of Cuba has long been a destination that intrigued Americans, but since the 60s they have not been able to visit and see for themselves.  Although American cruise ships are no longer allowed to visit Cuba, with our General License we can continue to visit Cuba in support of the Cuban people.  See the vibrant and colorful capital city of Havana, where the music and artistry is sure to capture your heart.  Don't forget about the salsa dancing!  Go back in time on a classic car tour, where you will see vehicles that have been on the road since before the embargo in 1962.  Visit a large farm outside the city and learn about their sustainable methods.  Share ideas and information with the locals about farming and technology.  Travel into the countryside to Vinales Valley, the foremost tobacco growing region.  Enjoy a mojito and a cigar factory tour, and you have the makings of a fun winter getaway!

Dates Available
  • February 15 - 22, 2024 SOLD OUT


Day 1:                                      Miami, FL / Havana, Cuba
Meet your Tour Manager and fellow travelers at the Miami International Airport for an early evening flight to Havana, Cuba.  After a short 1-hour flight, we are greeted by our local Rupiper Tours’ Cuban Guide and check-in to the Grand Aston Resort Hotel. Completed in 2022, you will find the Grand Aston to be modern and elegant, boasting views of the Havana Bay.  Enjoy a welcome dinner at a paladar (small, family-owned restaurant where traditional, homemade local foods are served) and see for yourself that wonderful, high-quality food is available in Cuba. D 

Day 2:                                      Havana
Enjoy the faded glamour of the 50s as well as the new carefully reconstructed architecture of the present, brushed in the vibrant and irresistible colors of Cuba!  Experience the Old Town on a walking tour, which takes you through the grand center squares to show-off the bustling capitalism that is so new to this country. Meet the owner of a new entrepreneurial project and learn what it takes for locals to open a business in Cuba.  Things have certainly changed from 20 years ago!  Following lunch at a paladar, depart for the Marianao municipality in Havana to visit The Angeles del Futuro project. Here young students strengthen their values such as altruism and modesty through a variety of circus techniques, such as acrobatics, juggling, contortions, balance, and trampoline acrobatics. Today, the project has a permanent pool of students who enter the National Circus School, and who later become part of the National Circus of Cuba. Return to the hotel to freshen up before dinner at another of our hand-picked paladar restaurants. You won’t believe the great food Cuba has to offer... as long as you know where to look! Following dinner, we celebrate our time in Cuba with a one-of-a-kind performance at the world-famous Tropicana Cabaret Show.  This “Paradise Under the Stars” open-air theater opened in 1939 and has changed little since its 1950’s heyday.  The program features authentic Cuban rhythms, music, and dance without ignoring the Hispanic and African heritage of Cuba.  You will love this unforgettable performance under a blanket of stars. B, L, D 

Day 3:                                      Havana
By now you’ve been seeing some really cool, old cars. Enjoy an introduction to Cuba’s historic past with a visit to A lo Cubano Antique Car Club and workshop. Interact with the president of the club and car owners to discuss the process of private ownership of these classic cars in Cuba, and what they do to keep them on the road.  Whether that involves swapping in a diesel engine or fabricating a custom part, Cubans have become resourceful mechanics out of necessity.  Take a step back in time and cruise through the heart of Havana in a classic 1950s car and relive the past.  Riding in our convoy of classics is truly a crowd favorite, as even locals stop to gaze at our parade.  Learn a little Cuban Flair with a visit to Habana Compass Dance project, a troupe of talented dancers and artists that blend traditional and new dance with percussion, energy and rhythm into an exuberant, infectious mix. Born from their Spanish and African-Cuban heritage, this upbeat performance will have your toe tapping!  Along with dance and music, Cuba’s African roots also have an important influence on the country’s culture and art.  Following lunch at a paladar, we visit Vi humos, an exclusive private project where guests will experience cigar rolling and Cuban rum tasting while listening to live music. The tone will be set for you to enjoy this beautiful location with their hand rolled cigars and Cuban rums while shopping for handmade Cuban fashion accessories and learning the owner’s personal story in the world of high-end Habanos cigars!  Return to the hotel to relax before dinner at a paladar - by now you may be sensing a theme. Paladars offer the highest quality of food versus the nationally owned and operated restaurants, because the families take pride in their craft and want only the best for you, whereas the nationally owned restaurants often leave much to be desired. Take the guesswork out and let us take you to our favorite restaurants! B, L, D 

Day 4:                        Havana / Pinar del Rio (Tobacco Country)  / Viñales Valley / Havana
After an early breakfast, we say goodbye to Havana and begin to see small patchwork farms as we travel west on a four-lane highway into the country.  Following the revolution, the government turned its attention to reclaiming some of the land that had been logged in earlier times. The land was terraced to control erosion and the terraces were planted with trees. Once in Pinar del Rio, you will see why this is the premier region for growing tobacco. Learn about Cuba’s famous crop as we visit the farm of Hector Luis Prieto. Born in the western Cuban town of San Juan y Martínez in 1972, Prieto grows tobacco on the same farm that his grandfather worked, a farm that was taken over by the Cuban government before he was born. However, the farm was given back to Prieto in 1995 and he and his father have continued the tradition of growing some of the best tobacco in the country. In addition, he is also the youngest person to ever win Habanos S.A.’s prestigious Man of the Year Award for production, an honor he picked up in 2008 for having the largest yield of high-quality wrapper leaf. Following lunch on the farm, we enter the town of Viñales to visit the mural de la Prehistoria and explore the town.  Admire the beautiful view of Viñales Valley before returning to Havana. Dinner will be at the hotel upon our return.  B, L, D 

Day 5:                                      Havana / Veradero Resort
Travel about 45 minutes west of Havana to visit a farm in Caimito. Here a university-trained agronomist settled on a badly eroded, brushy hillside ten years ago and began digging a well into the rocky soil.  While other nearby farmers thought he was crazy, after only seven months of using hand tools and 50 feet of digging, he finally struck a gushing spring of cool, clear water.  Today he is one of the most sought-after figures in Cuban culinary circles, providing over 60 varieties of vegetables, fruits, and herbs to Havana’s top rated paladars (private restaurants).  Visit the farm, and if his schedule allows, meet with the founder himself. Enjoy an incredible farm to table lunch before making our way east past Havana to the northern coast, and cross the Bacunayagua bridge. Built between 1956 and 1959, it is one of the seven wonders of Cuban engineering.  Arrive at our resort hotel, where you can kick-back and relax. Situated on Varadero, this is the region that Europeans and Canadians have been vacationing to enjoy sandy beaches, great weather, and fun in the sun.  This is your perfect chance to take a dip in the ocean, pool, or have a fruity umbrella drink! Enjoy the all-inclusive amenities of your resort & overnight. B, L, D 

Day 6:                                      Varadero Resort
This morning we visit the historic Casa Dupont (Xanadu Mansion). Dating back to 1928, this property has been carefully restored following its original construction plan. Enjoy a refreshing cocktail overlooking the ocean from this unique glimpse into Cuba’s past. Depart for the city of Cardenas for a look around, before we continue to the Sugar and Steam Train Museum. Learn about Cuba’s history growing sugarcane and see the steam train used to transport the product. Next up, we visit Finca La Luna to interact with the owners and workers of the farm. Tour the property and feast on an abundant country lunch. Return to your resort in Varadero to relax or enjoy the amenities. Dinner is at your leisure at the all-inclusive resort.  B, L, D 

Day 7:                                      Varadero Resort / Havana
We say goodbye to our wonderful resort and head to the fishing village of Cojimar to begin tracing Hemmingway’s footsteps in Cuba. Following lunch, we depart for San Francisco de Paula on the outskirts of the city, where Ernest Hemingway lived for twenty years. Visit Hemmingway’s winter home from 1939-1960, which was built in 1886 and now serves as a museum where visitors can see his 9,000-volumne library, living quarters, yacht Pilar, as well as the actual typewriter on which he wrote some of his greatest works. Visit a real working cigar factory, where Cuba’s famous export is produced. See the effort that goes into each cigar and decide for yourself if it warrants the price!  Return to your Havana hotel to freshen-up before your farewell dinner at Mansion Castillo, where art combines with a gourmet Cuban fusion menu. Enjoy live music on as Havana gives you a fun goodbye. B, L, D 

Day 8:                                      Havana / USA
Transfer to the Havana Airport for your return flight to USA.  B

What's Included

What's Included

International Airfare & Taxes from Miami (MIA)
All Meals as indicated:
B (Breakfast) L (Lunch) D (Dinner)
Beverages with Meals • Bottled Water
Nice Hotels • Cuban Travel Visa
Excellent English-speaking tour director and guides
All tours and admissions – no optional tours necessary!

Special Events and Sights


Classic Car Cruise • Classic Car Repair Shop
Tropicana Dance Show • Tobacco/Cigar Farm
Cigar Factory • Cigar Rolling Demonstration
Organic Farm • Viñales Valley • Private Paladar Dinners
Handicraft Market • Habana Compass Dance Project
Old & New Havana • Sugarcane Mill Museum
Vi Humos • Angeles del Futuro Circus Project • & More!
Two Nights All-Inclusive Resort


Testimonials from Past Cuba Travelers 

“The video is a treasure – Reliving our Cuban experience right from our recliners!! The fact that this was our 9th Rupiper trip says it all – you are the best!! Larry makes everyone feel like they are the most important person ion the tour. He treats us like family – makes the trip experience educational, exciting, and fun for everyone. Rupiper Tours always exceeds our expectations! I will always continue to recommend your service to our family and friends. Thanks again for a wonderful trip experience. I truly appreciate the video, as we are asked to share our experience with clubs and organizations in the area!”
– Dean & Jane P. (Nebraska)

“I wouldn’t change a thing. We saw and did so many things during our stay there. The food places were phenomenal. The Paladars were all so interesting with good mojitos and food. We looked forward to the convertible ride, and you certainly delivered! It was such a fun experience. The Hotel Nacional in Havana was unbelievable. Thanks for the video, it is fun to watch.”
- Garth & Sandi T. (North Dakota)

“One of the best trips we have ever had. The itinerary was great. The highway was fascinating, the rest stops interesting, it all added to the character. Enjoyed the agricultural visits. Came home happy and satisfied. Hope to go again – It was a magical place.”
- Robin C & Randy B. (Texas) 

“Service was very good. Brent was always on top of things and always kept a great attitude. All interactions were very good! The trip was great!! I really enjoyed it – seeing Cuba was very neat – I would definitely do it again some time.”
- Ron S. (North Dakota)

“Brent is excellent in all areas! Good job all around! You will be seeing us again!”
- Marcia & Larry W. (Nebraska) 

“Tour manager did a very good job making us feel comfortable. Always ready to answer questions and helping us relax. Thanks for the DVD – with that and our pictures we relived the trip. The only way to go to Cuba is on a tour.”
- Joan K. (Minnesota)

“Very good job. Really enjoyed Havana and the farms.”
- Anonymous 

“The trip was organized and planned well. We have recommended this trip to a close friend in our family.”
- Connie & Dennis N. (South Dakota) 

“Brent was excellent – knowledgeable, personable, and very accessible. We’d tour again with him any time. This will have to do as an overdue HUGE thank you note. It was good to do the cigar factory first, then work our way back through the process via the farms, both large and small.”
- Lee J. & Mary T. (North Dakota)

“The guides were excellent, very friendly. All was very interesting especially the tobacco farms. We have always had great experiences with Rupiper Tours. Loved the DVD and we met a lot of new friends.”
- Anonymous

“A very educational tour – Glad we went when we did. We are looking forward to our next tour with Rupiper Tours.”
- Harold & Bonnie D. (Illinois) 

“I was impressed that we saw so many sites. So glad we went when we did. Things may be different in future tours. We really enjoyed the different dining experiences. You have taken us to so many places we would never have gone by ourselves. Really enjoy traveling with Rupiper Tours.”
- Joyce & Wayland M. (Nebraska) 

“Tour guide was open to our questions to the best of his ability. He kept track of them and answered them for all to hear. The driver was incredible. Your office was always polite and helpful in a timely manner.”
-Jane H. (Pennsylvania)

“Our Cuban tour guide was very knowledgeable of the culture, country, informative, and truly pleasant. Driver was excellent. We had a very enjoyable trip and would certainly travel with Rupiper Tours again.”
- Clark & Anita M. (South Dakota) 

“We’ve enjoyed all of Larry’s tours. Thanks again for another great trip!”
- Larry & Margo B. (Indiana)

“Great job! The guides answered questions openly and honestly. We really enjoyed the Tropicana, farm sights, country, riding in the old cars, and much much more.”
- Verlaine S. (Kansas)

"All was excellent! We could not have asked for any better service! We really liked the cigar factory, the large vegetable farm, and the old car repair shop. Thanks for the video!!"
- Bill & Karen S. (Illinois)

"We enjoyed meeting all the people that were with us on the tour and the Cuban people we met. A lot of them could speak English. We have enjoyed all the tours that we were on with Rupipers and look forward to traveling with you again."
- Harlan & Sandra H. (Pennsylvania)

"We enjoyed the trip to Cuba very much. Lodging was very good. Glad we got to go. I'm sure you will see changes as time goes on."
- Gary M. (Missouri)

“Brent could always be found. Always cheerful. The guide did a very good job informing us of sights we passed as we drove along. The driver was a genius with that bus. Always helpful, always smiling. It was sheer heaven to sit on the patio of our historic hotel and have a drink while the ocean breeze washed over you.”
– Mary Ann D. (Iowa)

"Cuba is a great place to visit to get away from the cold and snow! The weather was fantastic! It was a very educational tour, learning about the resources, people, government, and historical sites. We were treated respectfully and felt very welcome. Once again we enjoyed all of the other travelers with the Rupiper group.  It always makes the eating, drinking, and touring more fun when we are together. Wonderful entertainment and fun car rides."
- Ken & Sharon B. (Indiana)

"Again this was a Rupiper Tour that was wonderful from beginning to end. Could not have been better. 5 tours with you and counting!"
- Mike N. (IL)

“Tour Manager did a great job. For us, this was a learning experience. That is what we wanted from our trip to Cuba. Both the guide and driver were wonderful. They were very friendly and were able to impart their knowledge to us. This tour was everything we hoped for. We came away with a deeper understanding of Cuba and her people.”
– Paul & Jean B. (Nebraska)

“Trip to Cuba was very good and interesting. Some things unbelievable. The people were friendly and the guide was great. Trip #10 with you, and we would do it again.”
– Paul & Ila K. (Iowa)

“This was a wonderful trip. It brought home the fact that people are the same everywhere. All we need is family, enough to sustain ourselves, and freedom from war and fear. If we could cross borders to accomplish this, the world could be a wonderful place!”
– Kaye H. (California)

"Brent went above and beyond and so much more. The guide was great! Very knowledgeable and had an answer for every question. I loved the whole trip, but riding in the old cars was my favorite!!! What a hoot! I want to go back in 5 years!"
- Victoria M. (Pennsylvania)

"This trip was one of our favorite places we have ever traveled.  The guide was great. So much fun and he gave us a world of knowledge. He presented himself and his country so well. The bus driver was safe and a perfect gentleman. It was all new to us and we most enjoyed the farm country and seeing how the people live. We want to go back in a few years and maybe see the changes. If we ever get to, we want to see our guide and driver again!"
- Cathy & John A. (North Carolina)

"Outstanding in everything! A great trip and excellent time to visit Cuba before the tourists cause changes."
- Ernie & Jan M. (Nebraska)

"Very good, always felt we were going to be taken care of. Especially with the food. We were glad to experience Cuba and its people. We enjoyed our adventure, Thank You."
- Gary & Marilyn M. (Missouri)

"Larry was great. Friendly and really helpful and a fun person to be with. The guide and driver were knowledgeable and professional. Our favorite sites were the cigar factory, farms, and car shop. Your office answered all questions and phone calls promptly. Thanks for the DVD, it's a great way to reminisce about this trip. Thank You!"
- Larry & Mary L. (North Dakota)

"Everything was great with Brent (Tour Manager). He was easy to approach with a question. The tour was well organized. Our visits to sites and restaurants were preplanned so well. Rupiper Tours is the best at doing this. The guide was excellent. We loved his sense of humor too."
- Dave & Sue S. (North Carolina)

"Very interesting trip with great service! Everything was well organized! Our guide was friendly and spoke excellent English. Loved his insights about his country and culture. Our driver was the best! Another wonderful Rupiper Tour! Loved the tour, the fellow travelers and guides. Thanks for the great DVD too!"
- Fred & Carole B. (Illinois)

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