Cuba Travel Checklist: 30 Things to Do Before You Fly
Documents, cash, flights, health prep, what to pack, what to download, what to research — everything you need to sort before you leave for Cuba, in the order you should sort it. Miss one of these and you’ll feel it on arrival.
Cuba Travel Checklist: 30 Things to Do Before You Fly
Every document, booking, download, and preparation you need sorted before you board. All 30 in one place.
Cuba is a trip that rewards preparation and penalizes the lack of it more than most destinations. The cash system is cash-only and ATMs are unreliable — if you arrive without enough, you’re stuck. The tourist card is required at check-in and you won’t board without it. US travelers need to understand the OFAC license framework before they fly, not on the plane. Medications you run out of may be impossible to replace in Cuba. The offline map you didn’t download becomes very relevant when you have no data.
None of this is difficult to sort out. It just requires doing it in advance. This checklist covers all 30 items, organized by category, with a short explanation of why each one matters and a link to the full guide wherever one exists. Print it, save it to your phone, or work through it category by category in the weeks before departure. The items at the top of each category are the most time-sensitive — the ones that require longest lead time or have consequences if skipped. Work from the top down.
Jump to category
Items 1–5 in the Documents section and items 7–9 in the Money section need sorting at least 4–6 weeks before you fly. Passport renewal takes time. Tourist card sourcing depends on your nationality and airline. Exchanging cash and organizing your travel insurance requires advance research. Everything in the Tech and Packing sections can be done the week before — but only if the first 15 items are already handled.
Documents & Legal — Items 1 to 6
Money & Finance — Items 7 to 11
Flights & Arrival — Items 12 to 16
“The three things that cause the most stress on Cuba trips: not having enough cash, not having the tourist card, and arriving at the Viazul terminal to find the bus to Trinidad sold out. All three are preventable with one afternoon of advance planning.”
Accommodation — Items 17 to 19
Health & Insurance — Items 20 to 22
Tech & Connectivity — Items 23 to 25
Packing — Items 26 to 28
Research & Cultural Preparation — Items 29 to 30 (but really, the whole section)
Beyond the 30 items above, invest an afternoon in reading about the specific places you’re visiting. If Havana is on your itinerary: the complete Havana first-timers guide. If Trinidad: the Trinidad Cuba travel guide. If Viñales: the Viñales valley complete guide. Research 3–4 paladares in each destination you’re visiting and save their WhatsApp numbers. Read the tourist traps guide and the Cuba travel scams guide. None of this takes more than 2–3 hours and it materially improves the trip.
The one thing this checklist can’t do
It can’t prepare you for how Cuba actually feels when you get there. The chaos at the CADECA exchange line. The mojito that costs 50 cents from a man who makes them out of his kitchen window. The view from the Malecón at sunset when Havana turns gold. The way a good paladar dinner feels when you’ve eaten cheaply and well and the food is actually excellent.
But the checklist handles the logistics so none of the above gets derailed by arriving without a tourist card, running out of cash in Viñales, or spending a day in a pharmacy trying to find ibuprofen.
Do the boring preparation. Have the extraordinary experience. That’s what this checklist is for.