READING: Check out your local library for travel books on Cuba. We read a bunch, and brought with us Fodor's and Lonely Planet (I used 2015, but the updated version is here).
FOCUS: Decide what kind of trip you want to do. Food? Rum? Cigars? Dancing? Historical? We picked a tour with OnCuba Travel that focused on food. They were even willing to work with us on price and cut off the last day of the Yuca & Mojito trip so that we could afford it. The reality is that tours are easiest for foreigners these days because so few Cuban businesses are online, and then at least you know you met visa requirements in case you are audited.
REGULATIONS: Speaking of tours, OnCuba was great about obtaining our plane tickets, sending us our visas, and arranging our internet cards so we wouldn't have to spend time on our vacation standing in line. The visas were a concern for me as a rule-following lawyer, but we filled them out and I'm not even sure that Cuban customs does anything with them.
TIPPING / CASH: The one thing I wish OnCuba had prepared us for is how much currency to bring and what to tip our guide, driver, casa particular host, restaurants, etc. Because there are few ATMs and I'm not even sure they work with American bank cards, you really have to bring a ton of currency with you, probably about $50 each day or more, depending on how many souvenirs you want to bring, and you have to prepare in advance because it's best to bring it in euros or Canadian dollars. We almost didn't have enough money at the end to tip our driver and guide, even though we loved everything they did for us.
|Hilarious mistranslation on a tablecloth at our casa particular|
GO NOW: Lastly, I would recommend visiting Cuba sooner than later. It is changing fast. My coworker visited his family in Cuba two years ago. It was grungier and no one had cell phones; these days they are doing renovations and cleaning things up, and everyone has smart phones. Havana was blessedly free of Starbucks and McDonald's, but the more open Cuba becomes, the more these businesses will supplant the existing economy of state and local businesses. Moreover, we saw plenty of cruise ships visiting Havana, which the locals (and I) are disappointed by. If you are going to visit Cuba, really dive in and support the people with your tourism dollars. Don't just check off a box on your travel list and buy a quart of rum and some cigars.
Thanks for reading, I hope this has been helpful!