On December 17, 2014, President Obama announced the reopening of an American Embassy in Cuba, after nearly half a century of no relations between the U.S. and the island nation. But intrepid travelers have been visiting Cuba for a while, applying for travel licenses for People-to-People Cultural Exchanges. Things have changed rapidly with the influx of new visitors, making travel easier in some ways and more complicated in others. Contact our bookings team to understand whether this is a destination for you and how best to visit. .

Cheat Sheet

  • Sleep…in the centrally located Parque Central
  • Experience…a ride in a classic DeSoto or Buick convertible
  • Splurge…on piece of art from a contemporary Cuban artist
  • Eat…at paladares such as Atelier and Café Laurent
  • Drink…a mojito in the garden of the Hotel Nacional
  • Savor…the sounds of the live music at Café de Paris and Café Taberna
  • Visit…Ernest Hemingway’s estate and admire his rooms exactly as he left them
  • See…a ballet performance—or a rehearsal—at the Gran Teatro de la Habana
  • Shop…pre-trip for items to leave behind such as baseballs and school supplies
  • Know…that as an Indagare member you can contact our Bookings Team for customized recommendations, expert guides, special access and itineraries

Lay of the Land

“We left the way one leaves a cherished but impossible love: our hearts heavy with regret but beating with great hope.”
~Mirta Ojito

Havana is the largest city in Cuba with over 2 million of the country’s 11 million inhabitants. The three principal areas of interest to the tourist are Old Havana (Habana Vieja), and the once glorious residential areas of the Vedado and Miramar. The Malecón is the famous oceanfront boulevard, where you may see waves still wash over the walls at high tide and, at virtually any time of day, young lovers can be seen strolling.

Recent News

President Obama’s December, 2014 announcement regarding the U.S.-Cuba diplomatic relationship means many things for the island nation that so famously sits just 90 miles off the coast of Florida—but above all, it has meant a massive influx of travelers to a nation with primitive infrastructure and limited hotels.

Indagare has been taking travelers to Cuba on Insider Trips for seven years. Half a dozen of our travel experts have scouted the destination, making sure we are up to date on the best hotels, restaurants and — most important — guides who bring their insider access to each trip.

Read this Destination Guide on our picks, as well as Havana Now to find out the most current in places. Members can also contact our Bookings Team for help organizing their trip to Cuba.

Getting There

Americans traveling with licenses can fly directly from Miami and according to reports, soon from many more American cities as U.S. carriers are planning to add direct flights. There are flights from London as well as daily flights from Mexico and Canada. Private charter flights can also be arranged but most will be on the Cuban charter airlines so the interiors will be closer to those of a Greyhound Bus than to a NetJet.

Getting Around

Much of Old Havana is a car-free zone and is best explored on foot so you can take in the architectural details of the beautiful buildings and squares. Pedi-cabs do criss-cross Old Havana so if you are weary, you can hail one and for a few pesos ride back to your hotel. Outside of the main hotels and major tourist sites, you will usually have a choice of regular cabs, vintage cabs (from Buick convertibles to glistening DeSotos) and horse and buggies.

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Beyond… Havana

Consider combining your trip with one of these destinations.

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