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particular contacts, José approached a fellow in a mint sky blue 1956 Chevrolet, asking if he was looking for a fare. Within 15 minutes, Olivia had a cheap, cool ride directly to an affordable, centrally located home where the English-speaking hosts awaited her with a frosty lager. We ran into her later that week and she told us she was having the trip of a lifetime; her story may have turned out differently were it not for her moxie.

      Shortly thereafter I met Jim, Blake, Kevin, and Jeff, four bros from New York who came to Havana on a quick whim of a trip. On Day 2, Kevin tumbled into the sea after slipping on the moss-slickened rocks at the Morro-Cabaña. He surfaced quickly, holding his iPhone above the water as his friends fished him out. They made their way back to their casa and began hunting for raw rice in which to plunge the phone overnight in an effort to salvage it—a trick that works, I’ve found. Night had fallen by this time; they didn’t know where to buy rice and no stores (let alone bodegas, where most Cubans get their rice) were open. The quartet popped into a restaurant and in broken Spanish asked one of the waiters if he would sell them some rice. A diner overheard their conversation, rose from the table where he was sharing dinner with his family, took the guys to his home, gave them some rice (refusing payment, of course), and invited them back the next day for some coffee and conversation. They were thrilled and so was I: here were four dudes whose Cuba trip could have been filled with a classic car tour, mojitos, jineteras looking for tricks on the Malecón, and getting sick on Cohibas. Instead, they embraced serendipity, solidarity, and the spirit of experiential travel. I don’t know if they ever got the iPhone working, but I know they made indelible travel memories.

      For female travelers, Cuba can be a jumble of contradictions vacillating between machismo and chivalry, honesty and grift, hordes of admirers and moments of loneliness. Solo travelers, especially, can have a hard time meeting other like-minded foreigners since connection opportunities are few and far between: the hostel concept is virtually unknown and there are no “expat” bars or hangouts like you find elsewhere. While there are Wi-Fi parks across the island where you can befriend other foreigners, many visitors prefer to embrace the off-line culture still prevalent in Cuba—especially since Donald Trump became US President. Then there’s what Rebecca Solnit calls “Manistan” in her book Men Explain Things to Me and I call “Macholandia”—a republic unto itself where men are all-knowing and too sexy for their own bad selves. As one expat friend recently observed: “There’s entirely too much testosterone on this island.” This machismo often manifests itself in sexual innuendo, regardless of age difference, race, size, origin or sexual orientation: he’s 80 and you’re 25? He’ll make a stab at it. You say you’re gay? He’ll say you’ve never had the right man. Old travel tricks are likewise ineffective: wearing a wedding ring—or even traveling with your actual husband!—won’t deter Cuban men from open propositions, brazen come-ons, and practicing the local custom of “piropos.” Loosely translated as “flirty compliments,” these run the gamut from creative to gross, fall-on-the-floor hilarious to seriously disrespectful. One of my all-time favorites was when a man pedaled by on a Flying Pigeon (1 million of these Chinese bikes were imported during the economic crash of the 1990s known as the Special Period) saying: “Your name must be Alice because looking at you sends me to Wonderland.” On the flipside, I was walking Toby in the park last week when a guy said to me: “Ay mami, put that leash and collar around my neck, let me be your dog!” Less endearing and not at all appealing. If you don’t speak Spanish, piropos are easier to pay no mind, but many times it’s just a sexually charged hissing sound—much harder to ignore. If your hackles jump at every piropo thrown your way, it can get oppressive.

      Given this scenario, it can come as a surprise at how empowered Cuban women and girls are. In some ways, the history of Cuba reads like a feminist tract, partly explaining this seeming contradiction. Machete-wielding women known as mambisas galloped into battle during the Second (and definitive) War of Independence, gaining fame for their valor and determination. Women played a definitive role throughout the Revolution as well, though you wouldn’t necessarily know it from the image of bearded guerrillas descending victoriously from the mountains projected by the international media. As Julia Sweig states in Cuba: What Everyone Needs to Know, “Behind the macho bravado that captured Cuba and the world’s attention were a host of extraordinarily brave and talented women who made survival and success possible.” Indeed, there were history-makers like Melba Hernández and Haydeé Santamaría, the only women who fought in the attack on the Moncada Barracks, the seminal event in the nascent revolution; Celia Sánchez, who took to the Sierra Maestra, rifle in hand, alongside Fidel, Che, Raúl, and the rest; and Vilma Espín, who organized forces in the city—she would go on to marry Raúl Castro and lead the charge on policy changes related to gender parity and rights until her death in 2007. Nevertheless, the binary gender paradigm is still deeply rooted here—cooking, cleaning, and child rearing are mostly the purview of women, while men play sports, fix cars, and take out the garbage. Never mind that women make up 69 percent of the professional workforce, more than 60 percent of scientists with advanced degrees are women, and the emerging private sector is full of entrepreneurial females: restaurateurs, designers, and yes, even bike mechanics and metal workers. Like most things in Cuba, or anywhere for that matter, you take the good with the bad and this island, the biggest in the Caribbean, has much more of the former than the latter. Importantly: from the cities to the countryside, Cuba is a very safe travel destination overall, no matter your gender.

      This island, too often falsely characterized as “stuck in time” or “preserved in amber,” is in constant evolution and these days, changing fast. There are many reasons for this rapid transformation, some more evident than others, such as the arrival of (for Cubans) new technologies including cell phones, internet and Wi-Fi, and digital television. Another major factor is the ongoing economic reform package known as the Lineamientos. Set in motion in 2010, these far-reaching reforms permit Cubans to buy and sell their homes and cars legally for the first time since 1959; relaxed travel restrictions for Cubans including doing away with the exit permit previously required and allowing residents to remain off-island for two years; and made it possible to open private businesses. This has injected new energy into daily life and spurred creativity and productivity in a land where blinking Christmas lights used to be the height of marketing and it was impossible to find food after 11 p.m. Today, there are 24-hour restaurants, Cubans of means bar hop until daybreak, private galleries host frequent openings, public transport options are varied, and you can have your iPhone repaired while copying the latest Netflix and FX series onto your hard drive. This is a breath of fresh air for Cubans with the resources to launch and patronize these businesses but a nasty taunt for the two out of three people who work for the state, the majority of whom earn the average monthly salary of $29CUC—and can only dream of owning a smart phone or cutting into a steak.

      The other dramatic change affecting lives across the island is tourism. In 2017, international arrivals broke records, with more than 4 million visitors choosing Cuba for their foreign vacation. This has deposited over 3 billion dollars in government coffers, with revenues going to national programs including the universal health and education systems, infrastructure upkeep, and massive development projects like the new port and industrial zone at Mariel. Nevertheless, the country has been caught unprepared, with the sudden influx of visitors causing shortages of hotel rooms and transport; onerous lines at immigration, baggage claim, and money changers at airports (Havana is particularly bad); and a distortion of the local economy. Known as the “inverted pyramid,” where a taxi driver, guide, casa owner, or anyone working in tourism makes more than a neuro-surgeon, lawyer, or engineer, it’s something talked about all the time—from the street to the highest levels of government. Throughout my 1,800-plus mile road trip exploring the 100 places in this book, Cubans were incredibly vocal about the problems created by tourism and how it’s affecting their daily lives. In Trinidad, where every other house rents to foreigners and makes sure they have a bountiful breakfast, Rogelio told me: “A pineapple costs 25 pesos here—when you can find them. Before I got three for that price.” He went on to lament how the vegetable market was stripped bare last time he went to buy produce to feed his family. On the other side of the island, Alicia from seaside Yumurí explained what’s happening in her hometown: “We’ve always lived off whatever we could catch—octopus, lobster, and fish. But tourists can pay more and fresh fish now costs 35 pesos a pound; on my fixed income, I can’t afford it.”

      The

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