Preparing for a Trip to Cuba

Tomorrow morning I am living out a short-lived dream of traveling to Cuba. Like most travel-prone Americans, I've been eagerly awaiting my opportunity to slip through the door that President Obama left ajar.

The flight is only three and a half hours, less time than it would take to drive to most ski destinations in upstate New York. Of course, we still have to go through the horror of airport security and the added bureaucracy of traveling to a semi-restricted state, but it'll all be worth it.

Despite the rules and regulations of traveling to Cuba as an American, my friend and I did relatively little to plan this trip. Here are a few of the plans we did make:

Accommodations

To fulfill the people-to-people requirement, my friend and I agreed one of the best ways to increase our contact with locals is to live with them. We, therefore, agreed to go the AirBnb/Homestay.com route of finding Casa Particulars. To find a reputable accommodation, we planned this aspect of our trip in advance.

Transport

In addition to booking our plane ticket (which we did well in advance to save on airfare), we also coordinated with our home stay in Viñales to arrange a shared car to drive us from the airport to Viñales on our first night. Since we arrive in the late afternoon, we figured we might as well get all of the heavy travel out of the way on one day, calling that a "dead day", so we can wake up exactly where we want to be the next morning. We don't yet have transportation for our way from Viñales back to Havana, but I'm lucky enough to be traveling with a native Spanish speaker, so we're feeling pretty confident.

Travel Insurance

Cuba requires that visitors have medical coverage inside the country, so trip insurance is a must. I've already warmed to the idea of paying for travel insurance, having needed it once to cover a theft in China and once to cover missing luggage in Turkey.

There are plenty of options. (Unfortunately, my typical go-to of Travel Guard via AIG requires a paper submission, which was too much of a hassle this go around). Based on my travel mate's suggestion, we chose World Nomads. The standard policy plan, which we purchased for $51 each, can be found here.

Cash

Credit cards and ATM cards do not work in Cuba, so cash is king. My friend and I took out some money prior to the trip to make sure we're not stranded without funds.

Packing

Luckily, I'm traveling with a like-minded adventurer who doesn't mind packing light to avoid unnecessary airport lines. Here's my one backpack worth of stuff for a four day trip:

  • Shirts (3)
  • Dress (1)
  • Bathing suit (1)
  • Pants (2), both of which are light weight. I'm wearing jeggings on the plane.
  • Socks and underwear
  • Shoes (4): one pair of flip flops, one pair of casual walking shoes, a pair of sandals, and sneakers. (This is where I think I overdid it.)
  • Toiletries, including hotel sized shampoo/conditioner bottles and a really good bottle of sunscreen and bug spray
  • Medications, such as pain killers, and small first aid items like band aids
  • Electronics: camera, phone, travel adapter, and headphones. I'm happy to leave my internet (and responsibilities) behind.
  • Sunglasses. I have a feeling I'm really going to need them! (Shout out to Zenni, which was affordable enough to enable my purchase of my first ever pair of prescription sunglasses!)

Other than that, we're pretty much going to wing it! A museum here, a salsa lesson there, we'll see and experience Cuba one moment at a time.

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