logistics

As an American citizen, you need a permitted reason to travel to Cuba. I chose the ‘Support for the Cuban People’ category. This requires that you stay at privately-owned accommodations and support privately-owned cafes, restaurants, and businesses during your trip.

I booked a flight through American Airlines from New York to Havana, with a layover in Miami.

forms

• Electronic visa

• D'Viajeros form — fill it out within 7 days before your trip, you’ll need to add your visa number there.

hotels

• Elvira, mi amor
  
• Paseo 206
  
• AS Boutique Residence

cafés

• HAV_Coffee&Art
  
• Eclectico
  
• Color Café
• El Café

streets to stroll

• Mercaderes
  
• San Ignacio
• Avenida del Puerto
• Avenida de los Presidentes
• Avenida Paseo

cheat sheet

• You can’t check in online for flights to Cuba, so arrive extra early at the airport.

• Keep in mind the list of prohibited hotels for US citizens.

• Bring plenty of one-dollar bills for tips.

• Also, bring toiletries, hygiene products, packaged snacks, flashlights, batteries, and portable chargers to give as gifts to hotel staff and others you meet along the way.

• Many streets are quite dirty, so I’d avoid wearing new shoes. Stick with old sneakers or comfortable shoes you don’t mind getting scuffed.

• Always carry wet wipes, hand sanitizer, and tissues with you — they’ll come in handy more often than you think.

• The Havana airport doesn’t accept electronic boarding passes, so be sure to print a paper copy for your return flight.