How to see Cuba now: 5 group tours that meet new U.S. guidelines

When the Obama administration loosened travel restrictions to Cuba in 2014, many Americans began to take advantage of direct commercial air flights and cruises that stopped in the formerly off-limits nation. Things have changed under President Donald Trump.

Although still legally allowed to enter the country, individual Americans must travel with a licensed “people-to-people” group tour. Group tours are required to provide a full-time schedule of educational exchange activities, and an employee of the tour company travels with each group to certify that the schedule is maintained. Americans traveling to Cuba are banned from doing business with any entity that benefits the Cuban military’s commercial arm, which owns many hotels on the island. Tour operators have scrambled to provide approved lodgings that are up to American standards.

Nevertheless, Cuba is still the “fascinating, friendly, and safe destination that it’s been,” according to Tamar Lowell, chief executive of Access Trips. And going with a group has always been a good idea when it comes to Cuba. As Lowell points out, the country can be hard to navigate on your own. Experienced tour providers make sure that travelers spend their time well, cutting through red tape to get them to places of interest. After years of cultivating relationships, they are also able to connect Americans with Cubans in all walks of life.

“[Our] People-to-people learning adventures provide Americans with an opportunity to learn directly from the Cuban people about their daily lives, hopes and dreams, and the challenges they face,” says JoAnn Bell, senior vice president of programming at Road Scholar.

The following tours, all certified by the U.S. government, offer a variety of ways to discover Cuba.


From vintage cars to colonial architecture to vibrant plant and animal life, there is no shortage of photo subjects for Americans in Havana. For camera buffs, Espiritu Travel offers a tour led by travel photographer Jim O’Donnell, designed to help you document your trip with exceptional images. Groups are capped at a maximum of 10, allowing for plenty of individual instruction. Highlights include a nighttime photography class at the Fortress San Carlos de la Cabana, a walking tour/street photography workshop of Havana, and a visit to Fototeca de Cuba to meet Cuban photographers. Visits to a boxing gym and a dance festival present more opportunities to take photos. Prices for the eight-day/seven-night trip start at $2,600, which includes B&B accommodations, most meals and entrance fees to attractions. Flights must be booked separately. 

INFO Espiritu Travel, 800-387-1370,


Circumvent the issue of scarce hotel accommodations by bunking on a boat during your Cuba tour. Wilderness Travel’s Cuba Cultural Adventure tour offers seven nights aboard a 34- or 54-person boutique yacht with air-conditioned cabins that include private baths. Unpack just once during your trip, and explore a new part of the country every day. Disembark in Havana for a walking tour of Ernest Hemingway’s favorite sights, a visit to artist José Rodríguez Fuster’s studio and salsa music at Café el Taberna. Sail to Maria La Gorda and explore the country’s largest nature preserve, Guanahacabibes National Park, rich in wildlife and archaeological finds. On Isla de la Juventud, tour the Presidio Modelo, where the Castro brothers were held before the Revolution. Other stops include Trinidad, a beautifully preserved colonial city, and Cienfuegos, the only city in Cuba founded by French settlers and the home of the Benny Moré School of Art. Prices for the eight-day/seven-night trip begin at $3,781 excluding airfare, visa and taxes.

INFO Wilderness Travel, 800-368-2794,


Cubans have little disposable income to spend at restaurants, so there aren’t many places where visitors can walk in off the street to enjoy authentic meals. If you’d rather not be herded from one tourist cafeteria to another, choose Access Trips’ culinary adventure. Some of the country’s best food is served at a handful of paladares, small restaurants in private homes. With Access, you’ll be taken to these dining rooms in Havana and beyond. Also in Havana, have a daiquiri-mixing lesson from a bartender who made them for 40 years at El Floridita, where Hemingway was a regular. You’ll visit the tobacco and coffee plantations of the Viñales Valley and a fisherman’s open kitchen in Trinidad. Along the way, stops will include farms (where you will be treated to a home-cooked meal) and markets where Cubans buy their food. Prices for the eight-day/seven-night trip begin at $3,890, including accommodations at a B&B and most meals. Flights must be booseparately


Jazz Cuba runs a variety of tours throughout the year, but their Havana International Jazz Festival Tour is the choice for Americans who want to experience “the ultimate Latin music event.” Days are spent sightseeing: a walking tour of old Havana, a trip to nearby self-sustaining eco-community Las Terrazas, the ruins of an 1801 coffee plantation built by slaves. You’ll get premium festival passes (valued at $250), including tickets to the opening gala. In the evenings, you will have a choice of festival shows. Past performers have included Cuban stars like Armando Romeu, Chucho Valdés and Los Van Van, as well as American luminaries such as Max Roach, Carmen McRae and Dizzy Gillespie. The group stays at the upscale Melia Hotel Trip Habana Libre (formerly the Havana Hilton). The next tour goes from Sunday, Jan. 14 to Monday Jan. 22, 2018. Prices start at $2,499, including hotel accommodations, most breakfasts and lunches, three dinners and passes to Jazz Festival events and other attractions. Flights must be purchased separately.

INFO Jazz Cuba, 888-965-5647,


Road Scholar, famous for its educational tours led by university professors, offers a trip for three generations. Travel with your children and grandchildren to Cuba to learn about the country’s music and art, see Hemingway’s farm and play dominoes like a real Cuban. There is an excursion to Las Terrazas UNESCO Biosphere Reserve and a stop in Santa Clara, where Che Guevara is buried. Meetings with groups of older citizens and high school students give travelers a personal view of life in Cuba. Prices for the 10-day/nine-night trip start at $4,299, including hotel accommodations and 22 meals.

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