I have visited about 15 countries, which is quite a bit more than most Americans and paltry compared with the travel writers I follow on Instagram, like JetSetSarah, truly one of the funniest, most upbeat women I’ve ever met on the road, and Where’s Andrew, who somehow combines intrepid with mellow (and the two know each other because when you travel that much, your paths cross—it is known).
Some countries I’ve been fortunate enough to visit several times: three times to England; three times to France; three times to Mexico with a fourth later this year; and later this week, my third time to Cuba, a country I adore even though I can barely speak any Spanish. I’m returning with the Cuba Writers Program, co-led by the indefatigable Tim Weed, who knows everyone in Cuba, from one end of the island to the other, including the guy on the highway who sells fruit and who will slice off a sample for you with his machete. That’s right—Tim has friends who have machetes. He’s that kind of guy.
How to pack for Cuba? Well, it’s really hot there, so I don’t need to wear a lot of clothes. I can likely alternate through a couple of sundresses and survive in one pair of flip-flops and be okay. Though my first two trips to Cuba have taught me a few things:
– Pack Pepto Bismol, not because the food will cause problems—I loved the food and didn’t have any issues, but someone in the tour group will likely need Pepto.
– Pack toilet paper. I forgot this last year even though I meant to pack it. Then I endured a number 2 situation in the lobby of Hotel Florida in Havana last year where I had to go back to the abuelita sitting next to her basket of single-ply, single square toilet paper that she handed out one square at a time. Every time I asked for “Una mas?” in a pleading tone, she shook her head. I went back to her three times. So I’m not getting stuck in that situation again because let’s face it: one square of single-ply toilet paper doesn’t do much.
– Pack snorkeling gear. This is a first for me, but I learned I’m snorkeling, and renting gear in Cuba isn’t a reliable option so I rush-ordered some from Amazon, a company I hate. My new fins arrive in a few hours. Because that’s America. Or, I should say, that’s Jeff Bezos.
– Pack dancing shoes. I can’t dance in flip flops, and I’ve become spoiled by my Italian-leather, suede-bottomed dance shoes. This will be their first trip anywhere—they’re excited.
And then there are the packing essentials that follow me no matter where I go:
– My pool floatie. The world is three-fourths water, and that’s not counting all the glorious, man-made swimming pools everywhere. So my odds of bumping into someplace swim-able are good. That means my pool floatie goes where I go.
– My bathing suit. I pack this whether I’m going somewhere warm or cold because someone somewhere will have a hot tub or a swimming pool, and being in water relaxes me, especially after a flight.
– Klonopin. Sad to say, but me and my benzos are inseparable at this point; I can’t fly or sleep without them, though know that if you hang out with me between the hours of 7 a.m. and 11 p.m., you’re getting the pharma-free version of me. It’s only on airplanes or in bedrooms where I’ve gotta knock myself out. When traveling, I will share from my stash the following: Pepto, gum, tissues, tampons, maxi-pads, Excedrin, Band-Aids, toilet paper (within reason), vitamins, probiotics, hand sanitizer (again, within reason) and lemon ginger tea. I will not share my Klonopin—I don’t care how wound up you are or what you’re willing to pay.
– Lemon ginger tea. This is true no matter where I go, and was quite handy during last year’s trip to Cuba. I brought plenty, and handed out tea bags like candy. Lemon ginger tea soothes almost anything except a gunshot wound or a broken heart, though I would even venture to say it can indeed help alleviate a bad mood. It’s physically and emotionally potent, and I trust it.
– Books. Pretty self-explanatory.
– Scarves. Even to hot places. You never know when you’ll feel chilly, especially walking on a beach at night, plus scarves are the most versatile item of clothing anytime anywhere. You can tie up your attacker with one, flag down a taxi, stash away some snacks you took from the breakfast bar, or wrap an abandoned kitten. Lots of options with scarves.
– Hats. Just because I like hats.
You’d think given past travel experiences I’d have some hard-won expertise in packing, but the truth is I suck at packing. I often leave packing to the last minute, though I have friends who take the packing process very seriously and tackle their suitcases like a puzzle. The contents of their luggage are as diverse and as thought-through as their retirement portfolios. I am likely to show up in Cuba or any country with a bag full of Klonopin, swim gear, and books, but missing essentials such as underwear or sensible walking shoes. This has actually happened before—me showing up to a destination without underwear because I forgot to pack it. This may make me sound like a fun person to hang out with (“Hey! She’s gone commando, and she’s got Klonopin AND a pool floatie!”) but at age 44 and the mother of a teenager, I should know better. When I went to Japan in April 2013, a friend of mine came over and took a C-suite level approach to packing *my* suitcase. She coordinated and laid out outfits for the different days of the week, sorted out which shoes were necessary, and showed me how to properly roll clothes to make everything fit. She brought her A-game to the task, and truly, my suitcase never looked so well-organized. For her, packing is as much fun as the flight and the trip. I want to aspire to this, and maybe on this trip, I will try.