What to do in Havana with kids? Lots. Here’s the itinerary we followed and that worked great for the younger set. You’ll notice that we didn’t do a lot of museums, more walking around and interactive art and music experiences that were more engaging for 5- and 6-year-old boys. For tweens and teens, this could be tweaked to include more of the historical and political learning.
Land in Havana and meet your guide and driver. En route to your hotel, stop by the Plaza de la Revolucion, where Castro delivered some of his most famous speeches. Then cruise the Malecon to get a general overview of the city (don’t miss the 150 flag poles planted by the Cuban government to block views of the electronic billboard where the American Embassy would blast messages—the WSJ has a great article on it). After you get settled, head to La Nacional for a drink with sea views while the kids track the free-roaming peacocks then head to dinner at La Guarida, one of the most famous (and delicious!) paladars.
Begin the day attending a rehearsal of Habana Compas, a noisily awesome dance troupe that makes percussion equipment from wooden chairs and blends steps from traditional Spanish dance as well as African and Caribbean beats. Then head to the Arts and Crafts Market, a slightly kitschy but fun spot for souvenir shopping. (Look towards the far corner by the water for the more interesting art.) You’re now right by Old Havana, the most carefully restored section of the city (and one that resemble Cartagena for those who have visited). It’s completely gorgeous. The kids are bound to be hot and tired by now, so don’t want too long before scooting to lunch at Paladar Doña Eutimia (you can also check out the art school next door).
If you’re dying to see Hemingway’s House, you can visit Finca La Vigia, a short drive from the city. Keep in mind, though, that you can’t actually go inside the house, only peak in the windows. If you’re a Hemingway fan (ahem, like some of us who wrote our college thesis on him) this is worth doing. If not, skip. On our trip, we also managed to sneak in a private performance by Hector Quintana, a celebrated young jazz guitarist. Concert or no, don't miss the home of artist Jose Fuster, which feels like Alice in Wonderland meets Dali, come to life in a Cuban house. Back to hotel to relax and swim, then dinner at Ivan Justo. Tip: Ivan Justo is really close to the Parque Central hotel, so you can walk home from here and pass the Granma memorial, where the boat that carried Che and Fidel from Mexico sits. There's also other military gear such as tanks and such that little revolutionaries might dig.
This is your day to head out of the city. Pack your suits and drive to Las Terrazas, around an hour outside of the city. Skip the row boats but go for the ziplining if you’re feeling adventurous. Lunch at the rural restaurant La Casa Campesino then spend the afternoon swimming in the San Juan River. Back home for dinner at San Cristobal, the paladar where the Obamas ate as well as Beyonce and Jay-Z. The vibe was so fun when we were there that when the restaurant temporarily lost electricity, everyone cheered, ordered another round of drinks and the waiters passed out cigars to pass the time until we could see the food again.
You’ll catch your flight home this afternoon, but there’s still time to do some touring before you leave. Start with a visit to a local kindergarten where you can donate school supplies then tour a small farm to learn about organic composting. You’ll be joined by the owner of a local restaurant that buys all his herbs from the farm, and then you’ll return to his restaurant to prepare traditional Cuban dishes in the kitchen for lunch. With a full belly, head to the airport and settle in for the long wait. Hint: keep a deck of cards or some other easy game handy, because the check-in and immigration line can be an epic wait.