How I'm preparing for my trip to Cuba.


I’m headed to Cuba in a few days!

I’m so excited to dive into a new culture, feel the sun (it’s been Winter for a while here in Cleveland), detach from my business and truly enjoy some downtime.

The first question people always ask me about traveling to Cuba is about the logistics.

“Is it legal for Americans to go there?”

“How are you doing it?”

So, here’s what I know and how I’m preparing.

  • I hired a friend / travel agent for women (I know it’s too much) who lives in Cuba. Her name is Gabriella and she’s amazing. You can find her here.

  • I asked my friends who have traveled there recently what they’d wish they’d known before they left

  • I got a ton of resources from my friend Julie who just hosted her wedding in Havana- and luckily she has a ton of insight into traveling + and enjoying Havana. Check out her recent post here.

  • I read up a lot on Cuba- everything from the current political situations to where to eat to where Beyoncé stayed on her trip here

  • I saved a bunch of articles in Pinterest and on my phone (and printed stuff out)

  • Americans CAN travel (for now) directly into Cuba

  • You’ll be required when you book your ticket to choose a reason for your visit

    • I chose “Support of the Cuban people” and to qualify for that you have to experience and support the people of Cuba for 6 hours a day and I’m doing that specifically by staying at at privately-owned Airbnb, shopping local designers, eating at local restaurants, going to museums and on tours, etc.

  • You’ll need a visa that you purchase at your airline counter (typically- though it varies slightly by which airport you’re flying out of and which airline you’re flying so just look into that- it’s super easy to find out

  • I’m packing snacks + will purchase a few bottles of water in Atlanta (where I fly into Cuba from) since it seems that it can be a long day of travel

  • I’m bringing cash- you cannot use credit cards in Cuba and I’ll be exchanging money when I land in Havana. I’ll be planning to spend about $100 a day. Stuff still costs the same as it does here- tourists in Cuba will pay more than Cubans. The exchange rate is 1 to 1 for American dollars and a little bit better if you’re exchanging Euros to CUC’s (that’s the cuban convertible peso that ONLY tourists use). You cannot get any cash out once you’re there and you can’t use credit cards, so you must come prepared.

  • To figure out how much money I needed, I asked a few people about their trips and also looked into some stuff that I want to experience- and I’m bringing a bit more than I think I’ll need just in case.

  • I’m bringing some gifts and basic necessities for my host (Gabriella) and in general for people that I might meet that are kind to me or help me and that I’d like to thank somehow.

  • I’m learning some Spanish phrases that will help me- and I’ll have a little pocket guide for myself.

  • It’s going to be warm so I’m packing mostly light + easy-wearing looks. I don’t think it’s necessary to be super dressed-up daily, except maybe for a night out, so I’ll be pretty dressed-down. The exception is that I will be meeting a photographer while I’m there to take photos for a post-trip blog and to also be a part of my pitch to producers for my dreamy travel show aspirations. Jeans, tees, tanks, red tennis shoes, comfy sandals.

  • I’ll be making paper copies of my travel documents (passport, flight info, map & address to my airbnb, list of places that I want to go, phone numbers of Gabriella + a few people at home)

  • I booked an Airbnb in Old Havana- in walking distance to all the things- it was roughly $100 a night. Julie compiled a list of awesome lodging options for her wedding guests here.

  • I made a Pinterest board of lots of stuff that I want to see / do / eat / experience and the types of photos I want to take or have taken of me.

  • I downloaded these apps:

    • (to have offline maps of Havana on my phone while I’m not connected to wifi)

    • wiman (to locate free wifi around the city)

  • Here’s my abbreviated packing list:

    • passport + copy of it

    • printed airbnb info

    • printed flight info

    • printed travel agent info

    • health insurance card + copy of it (sometimes they check for this at the airport I hear)

    • reusable water bottle (maybe I’ll grab a water purifier, too)

    • cash

    • snacks for the entire trip

    • wet wipes (in case theres’ no toilet paper or hand washing available)

    • medicine

    • Spanish language book

    • small umbrella

    • camera + charger

    • bug repellent

    • sunscreen

    • bathing suit + sandals + coverup

    • travel bluetooth speaker

    • mobile charger

    • casual clothing + a few cute things for going out / dancing / dinners with some cool people

    • gum, candy, chocolate, art supplies, small art gifts for people I meet

I specifically planned this trip so that I’m not of much use to my team at Cleveland Flea for Spring Flea- it’s only 3 days after I get back. That might sound odd, but they are an amazingly-capable team and many times because of my own anxiety about business, I sometimes believe I’m being helpful when I’m really not.. And there are so many things I NEED to be thinking about that will help us grow and be better that don’t involve me gumming up the works of a well-run machine with my anxiety. So, for this trip, I’m doing what I would NEVER do in the past- leave when I could be working all my super last minute event things that probably don’t help us anyway.

And give myself some time to explore and think and be creatively inspired.

Stephanie Sheldon