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
  • Winter - 2024


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 45-minute flight on Delta Airlines, we are greeted by our local Rupiper Tours Cuban Guide and check-in to the famous Hotel Nacional, a former hot spot where celebrities such as Frank Sinatra, Winston Churchill, and Ava Gardner stayed during their lavish trips to Cuba. Enjoy a mojito on the large back patio overlooking the ocean. The beautifully manicured grounds and calming ocean views are sure to help you ease into the island mentality! 

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 and the bustling capitalism that is so new to this country. Learn the real story of the cigar industry in Cuba as we visit a major cigar factory.  The Cuban government rolls the production from every farm in Cuba, no matter what label or brand.  Recently the Cuban government changed their policy and now allows each farmer to keep a small portion of their tobacco production for friends and family.  It is hard to beat the great Cuban cigars that are rolled under the supervision and standards of the Cuban government.  The cigars all go through the same rigorous testing using specific methods during the rolling.  They even stop rolling if the humidity gets too low.  Always a very interesting visit!  Next is lunch at Sloppy Joe’s Bar.  Reopened in 2013, it was once a magnet for American celebrities and tourists during and after the prohibition years. It closed in the 60s, after tourism to Cuba dropped dramatically. Recognize the island’s artistic flair at Fusterlandia, an extensive public-art installation by local artist, Jose Fuster.  Colorful and whimsical mosaics cover over 80 houses of the fishing town of Jaimanitas, just on the outskirts of Havana.  Transfer to your hotel to freshen up for an evening dinner at a local paladar (private restaurant owned and operated without the government’s involvement), consisting of delicious choices.  You are sure to be surprised by the quality of food at our hand-picked restaurants.    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 classic car shop where they repair these cars, doing everything they can 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 re-live the past.  Riding in our convoy of classics is truly a crowd favorite, as even bystanders stop to gaze at the spectacle.  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, infections 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.  This evening 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.  B, L, D 

Day 4:                                      Havana
After last night’s enthusiastic performance, enjoy a late start before the short trip to Finca Vigia or “Lookout Farm,” the home of Ernest Hemingway.  Built in 1887, it now acts as a museum bringing to life the connection between Cuba and the author of many iconic novels, such as The Old Man and the Sea, For Whom the Bell Tolls, and Islands in the Stream. Also on display is Hemingway’s 38-foot fishing boat named Pilar. We continue to support the local Cuban people by dining at a paladar for lunch, where the owners work for themselves and the food is great.  We stop at a huge handicraft market, where you are sure to find a few souvenirs or artwork.  This is a great chance to speak with and learn from the artists who work and live on the island.  Before dinner, we hop in some classic convertibles for a leisurely cruise along Havana, seeing Revolution Square and the Malecón, the esplanade, roadway and seawall that stretches 5 miles along the coast of Havana.  Tonight we dine in one of our favorite Cuban paladars, a former sunflower oil production factory.  B, L, D 

Day 5:                                      Havana / Viñales Valley (Tobacco Country)
We say goodbye 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. We stop at this new forest, “Las Terrazas,” where people go to catch their breath from the hustle and bustle of Havana.  Las Terrazas has since become a lovely community surrounded by nature.  We continue southwest to Vinales Valley, a UNESCO World Heritage site, which is encircled by mountains and its landscape is interspersed with dramatic rocky outcrops. See traditional techniques that are still in use for agricultural production, particularly of tobacco.  Visit one of these small family-run tobacco farms, where they even demonstrate how to roll a Cuban Cigar.  Finish the day with a dip in the pool or an ice cold drink at our resort, before dinner.  B, D 

Day 6:                                      Viñales Valley / Pinar del Rio / Varadero Resort
This morning we travel a little further southwest into Pinar del Rio, the foremost tobacco growing region of Cuba.  Visit Vegas Robaina tobacco farm, a large commercial farm, and the only farm in Cuba to have a cigar named after them.  Here you will learn the details about farming and see how in-depth the care of each tobacco leaf really is.  See tobacco hanging in their drying barn as workers sort the leaves.  Head back toward Havana, enroute we stop at a farm in Caimito, about an hour outside of the city. Here a university-trained agronomist settled on a badly eroded, brushy hillside five 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.  Continue east past Havana to the northern coast, where our resort hotel will let you 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 7:                                      Varadero / Bay of Pigs / Varadero Resort
This morning we depart to a nearby sugar mill.  Until the 1960s, Cuba was the largest sugar exporter in the world with the U.S. receiving 33% of our sugar imports from Cuba. During the cold war, Cuba’s sugar exports were bought with subsidies from the Soviet Union.  After the collapse of this trade arrangement, accompanied by a collapse in sugar prices, two thirds of sugar mills in Cuba closed and 100,000 workers lost their jobs.  Production dropped eight million tons, to 3.2 million tons.  In 2008, sugar prices began rising as the result of a new interest and a greater demand for sugar. Today the sugar production in the cane sugar mills is estimated at 1.6–1.8 million tons. 400,000 tons are exported to China and 550,000–700,000 tons are used for domestic consumption.  The Cuban government will not allow visits to working sugarcane mills, but in 1999 this particular location was closed and transformed into a museum, allowing you to see the giant equipment and learn about the advancements in technology through the years.  See the thick black smoke bellow out of an old coal fire steam train as we board for a relaxing cruise along the countryside.  This short path used to be reserved for sugarcane transportation, but now it is just a fun way to relive the old days.  

Next we will take many of you back to a time that was eerie and a bit scary - the Bay of Pigs Invasion.  Travel southeast of Varadero until we arrive at the Bay of Pigs.  Have a look and re-live the days that shook the core of the American people!  Step foot on the very ground that led Americans to build bomb shelters during the 50s.  Travel back north, driving through farming areas with large center pivot irrigators. This is a stark contrast to the primitive farms seen to the west.  Tonight enjoy your final night in Cuba at the lovely resort. B, L, D 

Day 8:                                      Varadero Resort / Havana / Atlanta, GA
Transfer to Havana and the airport for your flight to Atlanta, where you connect with your domestic flight home. 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 Convertible Tour • Havana Compass Dance Project
Private Paladar Dinners • Large Tobacco/Cigar Farm
Bay of Pigs • Cigar Factory • 2 Nights All-Inclusive Resort
Fusterland Artistic Neighborhood • Cigar Rolling Demonstration
Viñales Valley • Sugarcane Mill Museum
Handicraft Market • Organic Farm • Soppy Joe's Bar
Classic Car Repair Shop • Classic Car Ride • Ernest Hemingway's Home
Tropicana Dance Show • and More!


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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