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Trinidad | Havana | Jazz Festival (Option 1)
Saturday, January 24, 2026 – Sunday, February 1, 2026
1 night in Miami, 3 nights in Trinidad, 4 nights in Havana
$4100/person (includes flight from Miami & travel visa)
Havana | Jazz Festival (Option 2)
Wednesday, January 28, 2026 – Sunday, February 1, 2026
4 nights in Havana
$2400 (excludes flight & travel visa)
Ashé Cultural Tours reserves the right to make changes to the itinerary in order to accommodate the availability of artists, lecturers, venues, accommodations and restaurants, and to account for unpredictable weather conditions. We remain flexible to ensure the best possible experience for our participants. This detailed itinerary reflects the experience for participants selecting OPTION 1 (recommended), which is an 8-night tour that includes hotel in Miami (Jan 24), hotel transfer to the airport (Jan 25), round trip flight MIA/SNU & HAV/MIA, and Cuban Tourist Visas.
OPTION 2 begins on Jan 28 in Havana for those participants who wish to enjoy a shorter 4-night stay in Cuba. For this trip, participants organize their own travel and tourist visa.
DAY 1 (Saturday) Jan 24, 2026 (Option 1 begins in Miami)
Make your way to Miami by flying into Miami International Airport (MIA). Our stay at Wyndam Garden Miami International Airport is included. Dinner is on your own, but if you arrive by 6PM and want to meet other people on the trip, Ken and Aaron will be at the restaurant a block from the hotel called Old Tom’s Sport Bar.
DAY 2 (Sunday) Jan 25, 2026
Today breakfast is on your own. At 8:15AM, we will gather in the hotel lobby and head to the airport for a 12:40PM flight (American Airlines) to Santa Clara International Airport. Make sure you eat breakfast/lunch, and consider grabbing a sandwich for the flight. Once we clear customs, we’ll board our coach bus, make a quick stop at the Che Guevara Mausoleum to learn about this important icon of Cuban revolutionary history. We will then continue on to Trinidad. After checking into our bed & breakfast, we will head out for dinner at one of Trinidad’s many fine restaurants (very likely Restaurante San Jose). As the evening progresses, you can retire to your homestay and enjoy the night air on the balcony, or wander the historical center seeking opportunities for music & dance!
Dinner included today
DAY 3 (Monday) Jan 26, 2026
After a delicious breakfast, the morning begins with a short tour of Trindad’s historic old town. Founded in 1514, this Unesco World Heritage Center is brimming with historical importance. Following the tour, we will enjoy a 3-hour horseback ride that skirts the edge of Trindad’s sugar cane fields and ultimately ends up deep within a tropical mountain rainforest. Along the way, there will be opportunities to stop and drink locally grown and roasted coffee and (for the bravest among us) to hop into a crystal clear, refreshing mountainside swimming hole. For those not interested in a horse excursion, we will help find alternative activities such as touring art galleries and museums. Trinidad is a lovely town to just wander and shop! However, be prepared for its cobblestone streets and hilly layout. This town can be a little difficult to navigate for visitors who are unsteady or have difficulty walking. In the afternoon, we will meet with local musicians, with opportunities to ask questions about both music and Cuban life/culture. Dinner will be on your own at one of the many fine dining establishments clustered around the city (we have recommendations like Los Conspiradores & Taberna La Botija) In the evening, there will be ample opportunities to seek additional music/dance.
Breakfast & Lunch included today.
DAY 4 (Tuesday) Jan 27, 2026
This morning we will tour the beautiful countryside and learn about Cuba’s sugar history, while visiting important and scenic plantations, mills, and historic mansions, including an active archaeological site. The tour includes visits to Mirador del Valle de los Ingenios where you can see a panoramic view of the Valley; the San Isidro de los Destiladeros (active archaeological site); and Manaca-Iznaga, a bustling little town with restored plantation buildings, a reconstructed watch tower, and a dark history of enslavement that is followed by social and economic renewal. In the afternoon, we will make our way down to Playa Ancón and enjoy one of Cuba’s many pristine beaches. Here you can buy lunch, enjoy a drink of your choice, and spend some time soaking up the sun, or relaxing beneath one of the large umbrellas along the beach. When we return to the city, be sure to find your way to a balcony for the 7:00PM sunset over the ocean. It is a sight you won’t soon forget! For dinner, we suggest you. head out with the new friends you’ve made and find an exciting spot, like Ambientes At Rintintin Restaurant or Muñoz Tapas.
Breakfast included today.
DAY 5 (Wednesday) Jan 28, 2026 (Option 2 begins at dinner)
After another fantastic breakfast, we will leave Trinidad behind us and depart for Havana. Our first stop, about 2 hours into the trip, will be Cienfuegos, known for its beautiful colonial buildings and even more beautiful bay, called by some “the pearl of the South.” During our short stay here, we will tour the town center (Parque José Martí) and the Moorish-inspired Palacio de Valle. The Palacio was built in 1917 on a dramatic piece of land that juts into the bay and is comprised of an outrageous jumble of tiles and turrets, crenellated edges and scalloped arches. Lunch will be at one of the top restaurants in Cienfuegos (I am hoping for Camila’s Restaurant, right on the Bay with picturesque views). After lunch, we will continue to Havana and arriving at our small, elegant, and beautifully restored colonial style hotel in Old Havana just in time for a home cooked dinner served on the rooftop patio. We hope you had some time to nap on the bus! After dinner, we plan to head out to an evening performance as part of the Havana International Jazz Festival!
OPTION 2 Guests will join us today at dinner. Our team will help you make your way to the hotel upon arrival in Havana.
Breakfast, Lunch & Dinner included today (option 1); Dinner included (option 2)
DAY 6 (Thursday) Jan 29, 2026
Today, we will explore Havana. The day begins with a guided tour of the Museum of the Revolution (situated within the former Presidential Palace), just a short walk from our hotel. From here we will go to the Partargas cigar factory in Central Havana, where we will learn about this iconic industry. Lunch will be at Jardín de los Milagros (Garden of Miracles), known for their delicious traditional preparations of sheep, goat, and beef! Next, we will explore this beautiful city in the back of 1950s classic American convertibles! During our 90 minute tour, we will enjoy panoramic views of the Havana skyline from across the bay, drive the entire length of the famous waterside boulevard (The Malecón), see the mansions on 5th Avenue, and visit the “Forest of Havana”! Our driving tour will end at the most beautiful hotel in Cuba, the Hotel Nacional, known for the historic mid-century gathering of mobsters such as Lucy Luciano, Santo Trafficante, and Meyer Lansky depicted in Godfather 2. From the hotel, it is just a short walk to the Pabellón (Pavillion) featuring some Latin jazz greats. Afterwards, we will return to our hotel for rooftop dining, take a few moments to refresh, and then back to the Jazz Festival performances at one of their many venues including: the National Theater of Cuba, Karl Marx Theater, Mella Theatre Gardens, Fabrica de Arte Cuba (FAC), and several others.
Breakfast, Lunch and Dinner included today.
DAY 7 (Friday) Jan 30, 2026
Today we have a guided tour of the four main squares in Havana’s Old Town (Havana Vieja): Plaza de Catedrál, Plaza de San Francisco, Plaza de Armas, and Plaza Viejo. We will walk on cobble streets, and see churches, altars, artwork, buskers, and maybe even a little carnival, and take in as much as we can of the 500 years of history of Cuba. After our tour, we invite you to find lunch on your own, and to wander the old town at your leisure. In the afternoon we will enjoy an exclusive private performance by members of the Conjunto Folcórico Nacional (Cuba’s national folkloric dance company). Another lovely home cooked dinner will be served on the rooftop patio of our hotel, we will again head out to enjoy evening Jazz Festival performances at one of their venues.
Breakfast & Dinner included today.
DAY 8 (Saturday) Jan 31, 2026
This is our last day in Havana and we have options! Weather permitting, we’ll take beach lovers to Playas de Este about 30 minutes east of Havana. Blessed with white sands and ultra clear aquamarine water, the beaches of Cuba are lovely. Alternately, this is also a great day to walk around the old town of Havana and relish in its beauty and history. There are craft markets, shops, and hidden alleyways still to explore. We can point you towards the Paseo del Prado (Havana’s tree-lined pedestrian boulevard), to explore Havana’s best outdoor artist market, which ends with a visit to Parque Central with its beautiful street views & historic hotels, and possible tours of the Capitolio and the elegant Grand Teatro de la Habana (Alicia Alonso). For those who prefer art over the beach, we will arrange for a guided tour of Museo Nacional Bellas Artes (featuring some of Cuba’s greatest artistic treasures) and/or several of the world-class private artist studios spread throughout Havana. In the evening, we will continue to enjoy the Jazz Festival at one of their many venues.
Breakfast and Dinner included today.
DAY 9 (Sunday) February 1, 2026
Farewell to Havana, Cuba! Option 1 participants will rise early and head to their airport for an early flight to Miami. Option 2 participants can join us on the bus, or make their own arrangements later in the day for their trips home. Safe travels! Thank you for sharing the experience with us.
Breakfast included today.