Get your Cuba papers in order.
It’s mandatory to have Cuban health insurance when visiting Cuba. You can purchase coverage from your airline carrier and will need to provide documentation when entering the country. So make sure to print any documents you need ahead of time, because, again, technology is spotty on the island. You’re also required to keep all papers for five years after the trip, so clear some space in that one folder where you shove all the important stuff.
Embrace your inner Luddite.
Have you been hearkening back to simpler times, when phones flipped open and twitter was just a pleasant bird noise? Well, Cuba can help break your screen dependence. Internet connection and Wi-Fi are rare on the island, and you have to purchase Wi-Fi cards at ETECSA if you do find a wireless spot. Don’t count on roaming, either. If you have to make an international phone call, head to a phone center.
Insider Tip: If you usually rely on Google Maps when wandering about unfamiliar terrain, you might want to consider downloading Galileo Offline Maps. It costs money but it might save you a headache.
Is your stomach growling ?
When you go looking for authentic Cuban food, look for the nearest “paladares particulares.” These are privately owned restaurants, with higher quality farm-to-table fare. The cost is about the same as other establishments, but the number of locals filling up at the paladares attests to the difference in quality.
Snag a souvenir.
Finally, the most obvious question — how many cigars can you bring back? Americans are allowed to bring back up to $400 worth of goods from Cuba, including up to $100 in cigars. Whether you share them with friends who haven’t graced Havana’s streets yet, is up to you.