Finishing up our world tour/airplane passenger torture project¹ was a trip from Baltimore to Havana, via Cancun. Before you scream Embargo!, neither my wife nor I are American citizens. Our daughter is, but it is fortunately not illegal for US citizens to visit Cuba as long as they don't spend any money there, at least according to America's most esteemed journal of law, medicine and gastronomy.

If for whatever reason you want to travel to Cuba from the East coast, you might find our experience helpful.

The flight

We took the United flight from Dulles to Cancun, went through Mexican customs and immigration, then took the Cubana flight to Havana after checking in again. Inbound, layover time was more than 3 hours so we could have comfortably checked a bag or two for those large bottles of sunscreen and other essential liquids. The trip back, however, was tight at 1h 55min, so we decided not to risk waisting time at baggage claim, and only brought carry-ons.

In retrospect, it was half of a good move. On the way back, going through customs, immigration, then walking from Cancun's Terminal 2 to Terminal 3 and checking in for the flight to Dulles is barely manageable in those 90-ish minutes after leaving the plane. However, we could—and should—have checked one of the carry-ons on the inbound flight, as sunscreen, diaper cream, and other toiletries are ridiculously expensive in Havana.

NB: You can easily walk from Cancun's Terminal 2 Arrivals to Terminal 3 Departures (or 3 -> 2 inbound). There is a shuttle that leaves every 30 minutes and goes Parking -> T1 -> T2 -> T3 -> Parking. The Cancun airport staff told us it would take us 25 minutes to walk from T2 to T3—and that it would take the shuttle at least as much since it makes those other stops—but hey! there's this van that magically appeared which would drive us to T3 for the low low price of $20. Google maps said it's less than a kilometer between terminals 2 and 3 so we smiled politely and walked away. It took us—three adults with a carry-on and a large shoulder bag each, plus a toddler in tow—less than 10 minutes. Kudos to United for letting us skip the long check-in line and making it to our flight without issues.

Entry

Serbian citizens don't require a visa, but Dora had only her US passport. We got her a visa in Cancun at check-in for 20 euros.

Cuban entry stamp is bright pink. They asked us before putting one in Dora's passport, so I can only assume they occasionally get US citizens who'd rather not have their passports stamped for whatever reason (cough, cough). The visa also gets stamped, so there is still proof of entry.

There were no issues going back through Dulles. The customs form asks you which countries you visited on the trip, so we did write we were in Cuba. The immigration officer at Dulles just asked if we were bringing any cigars back with us—of course not, we hadn't even smoked any while there!—and finished the fingerprinting in record time.

Money

Bring euros, and bring more than you expect. You can convert USD to convertible pesos (CUC) in any exchange office, but with their rates it's better to change dollars to euros in your own bank, then change euros to CUC once in Cuba. Also, convert some CUC to the peso nacional (CUP), if only for the ridiculously cheap ice cream you can buy on the street.

As for how much to bring, count on at least $20/person/day, not including the room or the 25 CUC exit tax. This would cover lunch, dinner, and a daily trip to the beach or a visit to a museum, monument, etc. Since you cannot use American credit/debit cards anywhere on the island, it pays to take more than you think you would need.

Homestay

The highlight of the trip! We booked this room on homestay.com, and could not be happier with how it turned out. Centro Habana, the neighborhood it's in, is definitely not for everyone—very safe, like the rest of Cuba, but also with dog poop and open trash cans everywhere you turn². Our casa particular was the opposite—clean, well-maintained, gaudy, but cute. Between our large air-conditioned room, the patio, and the open rooftop terrace, we could easily have spent a couple of days just hanging out there chatting with the friendly hosts.

Internet

Don't count on being able to get online at any point. We tried checking in online a day before the trip back, but none of the Havana Vieja hotels we tried had any prepaid cards available. Even if they had, there are no printers to print a boarding pass. Unless you're staying in a hotel, don't even think about wi-fi. Just bring a good book or two.

So, if someone's vacations response email tells you they're going to Cuba, don't count on them having any access, no matter what some self-important douche bag tells you.

Guidebooks

The only resource we used—and we used it multiple times per day—was the Havana Good Time iPhone app. Some of the information on working hours and prices is slightly outdated, but it is all still relevant, and it comes with an offline map of Havana that is—duh—much easier to carry around than the paper version.

Other DOs and DON'Ts

• Do take the Havana tour double decker bus at least once.
• Do go to the Revolution Museum—the clunky propagandist English translations alone are worth the 8 CUC admission fee.
• Do try the excellent Coppelito ice cream.
• Don't waste an hour standing in line to pay for it with CUP—support their economy, and pay for it in hard currency like the tourist you're pretending not to be.
• Don't give any CUC to street performers, especially the kind that chases you down the street with a guitar.
• Do throw CUP at them.
• Don't drink the tap water.