8 Days

Price starting from: $5,995. Prices are in USD, per person, based on double occupancy.
OCT 17 – OCT 24
NOV 07 – NOV 14
DEC 05 – DEC 12

Minimum Age: 18
First Event: Welcome Reception at 7:30 p.m. on Day 1
Last Event: Arrival to Santa Clara Airport at 1:00 p.m. on Day 8

Discover inspiring Havana, Trinidad and Cienfuegos on an immersive, people-to-people program, featuring authentic firsthand encounters with locals from all walks of life, accompanied by an expert Cuban guide and a dedicated A&K Program Director.

INCLUDED Hand-Selected Boutique Accommodations
English-Speaking Program Director and Local Guides
Internet Access (Where Available)
Airport Meet and Greet with Transfers
Full Breakfast Daily; Select Lunches and Dinners
Entrance Fees, Taxes and All Gratuities Except Program Director
24/7 A&K On-Call Support
Guaranteed Departures with Just Two Guests

Please call 1-855-824-2495 to request a quote.



Arrive at José Martí International Airport, where you complete immigration and customs formalities and transfer to your hotel. Meet your Program Director and fellow guests during a special welcome reception and dinner at a local paladar (family-run restaurant) in Old Havana.


After breakfast at your hotel, visit the 18th-century Morro Castle, a hilltop fortress guarding the entrance to Havana Bay. Explore the fascinating Habana Vieja (Old Havana) neighborhood — a UNESCO World Heritage Site — strolling its narrow streets alongside a local architect. Visit the city’s four significant squares; learn of the buildings’ pasts; and discuss the challenges and successes of present-day restoration projects. Then, a local baseball expert joins you for lunch at a paladar to share how this historic pastime — and sports as a whole — plays a key role in Cuban society. Afterward, visit the San Jose Craft Market, interacting with residents as you peruse its wares. Next take a panoramic tour of Havana, seeing the Vedado business district, home to the University of Havana, the oldest in Cuba. Then, drive along the malecón (seawall promenade). Stop at Revolution Square to take pictures and learn the history of this political epicenter. Tour historic Hotel Nacional with a local guide, who brings this timepiece of Cuban history to life. Return to your hotel. Tonight, enjoy an authentic dinner at a paladar .


Travel through the Cuban countryside to Vinales in Pinar del Rio, pausing en route at Los Jazmines Hotel for panoramic vistas of the Viñales Valley. Upon arriving at Benito Camejo’s tobacco farm, its farmer shares firsthand knowledge of the production and drying process. Proceed to organic farm El Paraiso, where you sit down to a country lunch overlooking the Viñales Valle del Silencio. As you sample home-cooked Cuban cuisine, gain insight into daily life and organic farming practices from its owners and farmers. Afterward, farmers reveal how tobacco leaves are fermented and selected, a stage completed only by local women. Return to Havana, where you have dinner at leisure.


Visit Ernest Hemingway’s former home — Finca La Vigia (“lookout house”) — situated in Havana’s San Francisco de Paula neighborhood. As a specialist shares immersive insight, picture the author’s life during the more than 20 years he lived there. Continue to the picturesque fishing village of Cojimar, where Hemingway docked his boat, ‘El Pilar.’ Not only was the town his fishing base, it’s where he penned The Old Man and the Sea and For Whom the Bell Tolls. Sit down to lunch at a paladar. Then, pay a guided visit to Museo Nacional de Bellas Artes de La Habana, where a local expert guides you through its renowned Cuban art collection. While there, attend a private concert by the Cuban Institute of Music, a chance to experience Cuba’s rich musical history firsthand. Return to your hotel for time at leisure. This evening, gather with fellow guests and travel by “Yank tank” (vintage car) to a local paladar for an authentic Cuban dinner.


Travel to Cienfuegos, the aptly named “Pearl of the South.” Upon arrival, take an informative, guided walking tour of the scenic town, perhaps seeing a Cuban CUC store and pharmacy en route. Following lunch at a paladar, continue to Trinidad, where you check in to your hotel and sip a refreshing welcome drink. Take some time to unwind before gathering for a canchánchara cocktail-making demonstration — a classic libation born in colonial Trinidad. Then, sit down to dinner with fellow guests.


Take a guided walking tour of historic Trinidad, a 19th-century colonial gem and UNESCO World Heritage Site that’s all-but frozen in time. Stroll the cobblestone streets, seeing the soaring cathedral and elegant Plaza Mayor. Next, meet a local artist at her workshop and gallery, learning about the enriching community projects she is involved in. Then, discover the local marketplace at leisure, seeing intricate, hand-sewn table cloths, colorful papier-mâché models and local handicrafts. Next, attend an enriching Afro-Cuban performance at the Palenque de los Congos Reales, meeting afterward with its musicians and dancers. Drive to the “valley of the sugar mills,” pausing at Mirador del Valle de los Ingenios for panoramas of the valley. Then, visit the small village of Manaca and see the Iznaga tower, once a sentry post to keep watch over slaves working in the sugar plantation and mill. Return to your hotel and have dinner at leisure.


Depart Trinidad and return to Cienfuegos, where you meet with teachers and students at the Benny Moré Art School, named in honor of the famous Cuban musician. At Cienfuegos Graphic Workshop, meet young experts who are skilled in the arts of serigraphy and screen-printing. After lunch at a local paladar, attend a Cuban choir performance, getting to know the musicians and singers afterward. As the day comes to a close, cruise the Cienfuegos marina by catamaran, exchanging with fishermen and residents en route. Then, check in to your hotel. After some time to unwind, reflect on your journey with fellow guests at a farewell dinner.


After breakfast at your hotel, transfer to Santa Clara Airport in Santa Clara, where you board your homebound flight.