Joe Sandillo's 6-day Cuba Itinerary

Musicians in Havana, Cuba
Photo: Evan Lang/Getty Images

Joe Sandillo is a member of Travel + Leisure’s A-List, a collection of the top travel advisors in the world, and can help plan your perfect getaway. Below is an example of the type of itineraries he creates. To work with Joe, you can contact him directly at

Day 1: Arrive in Havana

Upon arrival into Havana’s José Martí airport, you will be met by an airport representative who will guide you through customs and private transfer to your accommodations. You’ll have a welcome briefing with your Almaz Journeys concierge and guide to go over your program and answer any questions you may have. In the evening, you have a reservation at one of our favorite privately-owned restaurants, called paladares; post-dinner, you’ll be treated to a cigar and rum tasting with a sommelier.

Day 2: Introduction to Havana

After breakfast, meet your guide for a driving tour in a classic American car, stopping at El Morro fortress at the entrance of the harbor; the seafront boulevard (malecón); Revolution Square; the Bacardi building; and numerous former Mafia haunts, including Meyer Lansky’s Havana Riviera Hotel. After a stop for lunch, take a walking tour of the four key squares of Old Havana, a UNESCO World Heritage site, joined by a local architect. After dinner at another favorite paladar, head to a show at the Tropicana cabaret.

Day 3: Arts in Havana

Today, it’s all about Cuba’s dynamic arts scene. Begin with a visit to a rehearsal of one of Cuba’s Afro-Cuban dance companies, before meeting with one of our local art specialist guides. You can visit the studios of established and
emerging artists, or the Cuban wing of the National Fine Arts Museum. After lunch, take a bike taxi tour of the city's public installations and street art. After dinner, visit the Fabrica de Arte Cubano (Cuban Art Factory) — an incredible art and performance space in a former factory.

Day 4: Cuisine and Culture in Havana

Visit some of Havana’s best local markets with a specialist guide to learn about urban farming and Cuba's food history. After a lunchtime cooking class, explore Hemingway’s Havana; visit his villa outside the city, exactly as he left it. In the afternoon, visit a community-based rumba dance project. After a short introduction and lesson by the project leader, you'll head to a venue to talk and dance with the locals to Afro-Cuban rhythms.

Day 5: Viñales

Depart Havana early this morning and head toward Pinar del Rio province and Viñales, in western Cuba — set in a beautiful valley, encircled by mountains and interspersed with dramatic limestone hills called mogotes. This is the heart of the tobacco-growing region of Cuba. Take a tour through the history of tobacco growing, visiting the tobacco plantations where
they still plow with oxen and even learning how to roll a cigar. You may also explore some pre-colonial indigenous cave developments, and even take a dip in a lake before enjoying lunch in a traditional house overlooking the picturesque valley. Your hosts have harvested and prepared your meal from their own farm (finca).

Day 6: Depart from Havana

Transfer to the airport for your flight home.

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