1950’s Time Travel, Cuba Uncovered

New AFS Hemingway’s Cuba

March 19-25, 2025

Havana – Cienfuegos – Trinidad de Cuba

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There’s no doubt it’s a unique destination to visit. So much history over hundreds of years, and so much of the culture still lives relatively untouched by outside influences. Cuba has the rare ability to maintain its distinctive identity. On our trip, you get to know the authentic Cuba up close and personal, the way the locals know it in three different regions.

This trip is far more educational, interesting, and memorable than a typical Caribbean vacay. We explore the magnificent heritage as we connect with the Cubans in daily cultural exchanges and activities, explore the depth of performing arts, like music, dance, colonial architecture, UNESCO World Heritage sites, museums, and more.

Ernest Hemingway

Oh, the fun we will have along the way on our unique visit… Hello Cuba! How about an AFS vintage Car Parade down the Riviera, screaming in our 1950s convertibles and exploring a national park in Russian Army trucks? We include delightful walking tours, workshops with locals, a visit to Hemingway’s Villa, handcraft markets, the iconic Cigar factory, a private AFS boat cruise along the turquoise bay, special lunch with artist Jose Fuster, hacienda dinners, visit to a dance company, resort beach time, salsa dancing under the stars, and so much more! Our guides are the best and make it so thrilling from bustling Old Havana to historic Trinidad and the neoclassic jewel of Cienfuegos.  

Travelers’ desirability to visit Cuba is proportionate to how long it has been closed to the outside world and inspires deep curiosity. Once a forbidden fruit, Cuba is now on the bucket list for so many people this year. We make it seamlessly easy to discover this island country under our new licensed “People to People” educational program” both legal and licensed for you. (Many companies offer Cuba tours, but Americans must be cautious on what is promised.) We have the best ground team who loves AFS and tailored the best for us and designed by Cubans for Americans!

Throughout, we include delicious meals, and the finest hotels Cuba can offer. Now is the time to go at a great price with everything included. This trip will sell out fast. Don’t miss our new ‘Cars, Cigars, and Cuba at large’ getaway. The best memories come from extraordinary experiences. Come…. Observe, explore, discover and learn about Cuba, a land beyond the ordinary.

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Our Glorious AFS Itinerary

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MAR 19    Fly USA to Havana. Round-trip air to Cuba is easy from Miami. American Airlines has 7 flights daily. More details to come in your trip tips with your detailed legal documents.  Land tour begins

Hola Cuba!   Arrival at Havana International Airport.  Meet your Authentic Cuba Travel tour guide and driver.  Private transfer to the luxurious Grand Aston Hotel located on the Malecon, Havana’s evocative 8km-long waterfront boulevard.  This luxury hotel is in the heart of everything.

En route, we’ll enjoy a panoramic visit to the Revolution Square (Plaza de la Revolucion).  Conceived by French urbanist Jean Claude Forestier in the 1920s, the gigantic square today is the base of the Cuban government and a place where large-scale political rallies are held.  It is here where Popes John Paul II, Benedict XVI and Francis celebrated an open air Mass during their visits to Cuba in January 1998, March 2012 and September 2015 respectively.  The Square was also visited by US President Barack Obama during his historic visit to Cuba in March 2016.

Private AFS group check-in and welcome cocktail on arrival to the Grand Aston Hotel. Evening: Welcome Dinner at the family-run restaurant paladar ’Arrecife’ and get to know your group.

Next, we attend one of the most traditional and popular ceremonies in Cuba, The Fire of the Cannon of 9 O’clock at the Fortress of San Carlos de La Cabana where Che Guevara established his headquarters after the Revolution came to power in 1959.

Tonight we have our Welcome Dinner and get to learn about your fellow group travelers.

Overnight Aston Grand Hotel   D (meals)

 

The Grand ASTON hotel in Havana is a fantastic experience for visitors seeking luxury and elegance. The hotel boasts stunning architecture and beautiful views of the surrounding area. Guests can enjoy world-class amenities such as a spa, pool, and fine dining options. The attentive staff ensures that every guest’s needs are met, creating a truly memorable stay. With its prime location and impeccable service, the ASTON hotel is the perfect destination for a luxurious and unforgettable vacation.

MAR 20   Exploring Old Havana.    

Breakfast at the hotel. Today we travel back in time to a time of popsicles, bikinis, hula hoops and sock hops.

AFS Vintage Car Parade –  Morning panoramic tour around Modern Havana in privately-owned vintage cars. One in 10 cars here are pre-1959. All cars are American – Chevys, Fords, Buicks, Pontiacs, Oldsmobiles. You’ll get delightful photos riding these convertibles through town.

Next, a visit to Havana’s Capitol building, Capitolio Nacional, designed by Cuban architects Govantes and Cabarroca and built by the American construction company Purdy & Henderson.  This is one of Cuba’s most outstanding architectural patrimonies. The dome is 300.96 ft. high (7 inches higher than the highest capitol building in the US).  Then we lunch at the family-run restaurant paladar ‘La Moneda Cubana’.

Enjoy a guided walking tour of UNESCO World Heritage Site, Old Havana.  Visit to Square of Arms, ancient military parade ground for Spanish soldiers and surrounded by impressive buildings such as:  Palacio de los Capitanes Generales, the former official residence of the governors (Captains General) of Havana, Cuba.  Palacio del Segundo Cabo. The seat of the second authority of the island, Castillo de la Real Fuerza. The second oldest fortress built by the Spaniards in the West Indies.  El Templete, a small neoclassical building marking the spot where the city of San Cristobal de la Habana was founded in 1519.

Then we explore the Cathedral Square, named after the masterpiece of Cuban baroque architecture: the Cathedral of Havana, built by the Jesuit order. We will visit the Experimental Print Making Workshop, a cooperative workshop where young lithographers ply their art.  Continue walking tour onto San Francisco Square, named after the Convent of San Francisco, this square was conceived in 1628, with the objective of supplying water to the ships trading with the metropolis.

Free time in the famous handicraft market of Old Havana, located inside the Almacenes de Depósito San José, an old warehouse on the harborside where you can purchase all sorts of crafts and souvenirs by local artisans. Or stroll over to the unique Arte Corte called “hair alley”, a community project of hair salons.

This evening we recommend you visit FABRICA DE ARTE – The Factory of Art (F.A.C.). This is one of Havana’s finest new art spaces located in a converted factory in Vedado neighborhood.  This is the brainchild of Afro-Cuban fusion musician X Alfonso. Celebrities Mick Jagger, Michelle Obama, Lady Gaga, Sting and Katy Perry have visited here. (Optional – Not included in tour cost) or enjoy some poolside salsa music at our hotel.

Overnight: Aston Grande.  B, L

 

MAR 21  Cienfuegos city, a UNESCO World Heritage Site, Boat Cruise.  

After breakfast, we board our coach for about a 3 hour drive through the beautiful countryside to Cienfuegos, in Central Cuba. This is the first, and an outstanding example of an architectural ensemble representing the new ideas of modernity, hygiene and order in urban planning as developed in Latin America from the 19th century.

Upon arrival at Cienfuegos city, we’ll have lunch at Paladar ‘Finca del Mar.’

Afternoon: Guided walking tour of UNESCO World Heritage Site Cienfuegos Historical Center.  We will visit neoclassical buildings around Paseo del Prado and the main Square Jose Marti, such as The Casa de la Cultura, home of another wealthy sugar baron, a stunning mansion in neoclassical style.  The Tomas Terry Theatre completed in 1895.  The Cathedral built with the donation of wealthy families like the Lebrancs, the Albis, the Terrys. Inside you find the reproductions of the 12 Apostles in stained glass imported from Paris. Also, the original machinery of the clock tower was built in France. Still in place and working.

Visit to Palacio de Valle. The eclectic building was erected at a cost of a million and a half pesos. French, Arabic, Italian and Cuban artisans worked with marble, alabaster, brass, glass and ceramic imported from Spain, Italy and the United States. The entrance is primitive Gothic style and leads to a dining room of Mudejar influence, which imitates the famous Patio of the Lions of Alhambra in Granada.

In the late afternoon, we enjoy a scenic boat tour around the Bay of Cienfuegos, which offers spectacular views of the city and the Jagua Fortress, built in 1745.

Continue by coach to charming Trinidad de Cuba.

Private check-in at the all-inclusive Melia Trinidad Peninsula Hotel, offering spectacular views of the Caribbean Sea and the Escambray mountains. You’ll love Cuba’s 5-star resort on the Caribbean Sea with its private beach, great spa, infinity pools with swim-up bar and all-inclusive amenities.  Dinner at the hotel.

      Overnight: Meliá Trinidad Peninsula               B L D

About the Meliá Trinidad Peninsula

Imagine immersing yourself in the warm waters of the Caribbean Sea, surrounded by the stunning Sierra del Escambray mountains. Picture the charms of the colonial city of Trinidad, with its rich history and vibrant culture. Welcome to the Meliá Trinidad Peninsula, the perfect destination for your next solo getaway.

This 5-star haven offers exceptional experiences for the curious and adventurous solo traveler. Whether you’re looking for relaxation, romance, or action-packed excursions, the Meliá Trinidad Peninsula has something for everyone. Unwind in spacious rooms, indulge in a world of dining options, and soak up the sun by the infinity or swim-up pools.  But the Meliá is more than just a hotel – it’s a prime location for exploring the best of Trinidad. Step back in time and wander the cobblestone streets of the colonial city, visit historic landmarks, and immerse yourself in the local culture.

MAR 22  Trinidad de Cuba, a UNESCO World Heritage Site, Jeeps Into The Mountains.

 Breakfast at the hotel.  This morning, we will board former Russian army trucks for Topes de Collantes National Park in the Escambray Mountain Range, Cuba’s second-highest mountain range- reaching 3,700 feet atop Pico San Juan. We will arrive at  Guayanara National Park.  Don your sneakers for some fitness.  We will follow an easy to intermediate hike for a few kilometers up to the Salto del Rocío, a beautiful waterfall that concludes with the Poza del Venado, featuring a natural pool in which visitors can cool off.  Along the trail, you will be thrilled by the memorable views of Pico San Juan, one of Cuba’s highest mountains.  A typical Cuban lunch will be served at Hacienda La Gallega.

Afternoon – Enjoy a walking tour around the UNESCO World Heritage Site, Trinidad’s Historical Center. This historic city is known for its cobble-stoned streets, pastel-colored homes and small-town feel. Visit the town’s Cathedral, Iglesia de la Santísima Trinidad, which most locals refer to as La Parroquial Mayor. The Cathedral, completed in 1892, replaced the original 17th-century church that was destroyed in 1812 by a hurricane.   The new construction, completed at the end of the 19th century, is rather simple on the outside, but the restored interior reveals a Gothic vaulted ceiling and nearly a dozen attractive carved altars.

Trinidad is well known for its pottery makers. Next, we meet with a family that has been passing the tradition for generations: the Santander. Then, we visit the Manaca-Iznaga Hacienda. The famous Manaca-Iznaga Tower, built in 1816, is 45m high, has seven floors and has 136 steps to the top. The restored hacienda is now a restaurant with a terrace overlooking the valley.

Return to your hotel.  This evening, you can explore the area or enjoy traditional local music at Casa de la Trova on your own.

Overnight: Meliá Trinidad Peninsula.      B L D

MAR 23   Trinidad – Havana

Savor a delicious breakfast at the hotel, then we’ll make our way back to the vibrant heart of Havana City.   Grab lunch at a spot that catches your eye along the way – the perfect opportunity to try some local flavors.

This afternoon, we’ll settle back into the luxurious Grand Aston Hotel in Havana. Spend some time relaxing, or get out and explore – the choice is yours!

As evening falls, get ready to experience the sizzling nightlife that Havana is famous for. This is a city that comes alive after dark, where the rhythms of salsa and jazz fill the air and the rum flows freely.  Immerse yourself in the spectacular shows at the world-renowned Tropicana Club, or opt for an intimate dinner at one of the legendary cabarets. The city is your playground.  Whether you prefer to dance the night away or enjoy some live music over a cocktail, Havana’s nightlife has something for everyone.

Overnight:  Hotel ASTON GRANDE     B

MAR 24  Hemmingway’s, Artists and Dancers – Havana.      

 Begin the day with a satisfying breakfast at the hotel, preparing you for a day filled with unique encounters and experiences.  Delve into Cuba’s fascinating history with a visit to the renowned Partagas Cigar Factory, established in 1845 by Don Jaime Partagas. This isn’t just a tour – it’s a chance to meet the artisans who carry on the traditions of this iconic brand.

Next, we head to Finca Vigia, the hilltop retreat of the legendary Ernest Hemingway. For 21 years, this villa was the author’s home and inspiration, where he penned some of his most famous works. Today, it’s a meticulously preserved museum offering a rare glimpse into the life of a literary giant. You’ll have the opportunity to see Hemingway’s original manuscripts, letters, and personal artifacts up close, as well as his impressive collections and library.

The afternoon brings a chance to meet some of Cuba’s vibrant artistic talent. Enjoy lunch hosted by Jose Fuster, the celebrated ceramist and painter who has transformed an entire Havana neighborhood into a living, breathing work of art. You’ll have the chance to meet the local residents who have become part of this creative project, and see the impact it’s had on the community.

The energy continues with a visit to the Havana Compass Dance Company, whose work has captivated international stars. This is your chance to meet the talented dancers and instructors, learn some of their moves, and experience the passion and dedication that goes into their craft.

The day concludes with a farewell dinner at ‘Atelier‘, one of Havana’s most acclaimed privately-owned restaurants. This intimate setting is the perfect place to reflect on the unforgettable encounters and experiences of the day, over a meal of exquisite cuisine.

Grand Aston Hotel           B L D

 

 MAR 25       Hasta la bye-bye Cuba!

After breakfast at the hotel, transfer to Havana International Airport for departure.

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LAND PRICE:  $3295 per person, twins share. (based on 20 participants. (Small group price incurs $200 increase). Gratuities for licensed guides, drivers, and porters of $85 will be added to the invoice for your convenience.

Single rooms limited costs an addition $895

 

Have you read the Trip Tips yet? Scroll to the top of the page and click the link.

Itineraries are prepared up to a year ahead and things can change.  Modifications may be made.  

 

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TBA