Arranging a visit to Cuba takes more forethought than most destinations. For Americans, the first question is “can I go legally?” A four-decades-old trade embargo denies most U.S. citizens and residents the right to travel to Cuba, although there are exceptions, and the restrictions loosen and tighten with shifts in the political breeze (the Clinton administration created a category of travel that essentially permitted anyone to visit Cuba; George W. Bush rescinded this “person-to-person exchange” allowance and flipped to a more harshly restrictive extreme). Understandably, thousands of U.S. citizens simply hop a plane to Cuba via Canada, Mexico, or other countries. Citizens of other nations don’t have this concern.

Cuba is a large island (almost 1,000 miles east–west) and many of the most popular destinations are far apart. In Havana, getting around is simple, thanks to an efficient taxi system. Traveling between cities by public transportation, however, can be a challenge. Domestic flights are best avoided, as safety is a great concern. Fortunately, tourists receive preferential treatment: modern air-conditioned buses connect the major cities, for example. And the country’s road network is well developed, although much deteriorated, poorly lit, and with unique hazards (such as lumbering ox carts). You can easily drive yourself around. Renting a car is recommended for anyone seeking serendipitous travel; cars are widely available, although their maintenance is usually very iffy and rental prices are outrageous.

In fact, Cuba is now vastly overpriced in almost every regard. Recently considered a bargain, the island is today one of the most expensive destinations in the Caribbean. Cuba’s financial institutions are not as progressive as those in Europe and North America, and you should not rely on being able to get by with your credit card. A good deal of cash is essential. U.S. citizens will need to operate on a cash-only basis, as credit cards issued by U.S. institutions cannot be used. (Also, notwithstanding Cuba’s vaunted health system, medicines are rarely available except in Havana and other key tourist venues, so come prepared with aspirin and other essentials.)

Be prepared for boring food and some sub-par accommodation. With few exceptions, food island-wide is uniformly bland (Cuba is well suited to anyone contemplating a diet). At the beach, most hotels operate as all-inclusive resorts, from which Cubans are barred. Havana has some splendid boutique hotels and several outwardly attractive but otherwise second-rate “deluxe” hotels dating back to the Mafia heyday. Cuba’s hotels are recommended only if you’ve little interest in engaging with Cubans. Far more rewarding and enlightening is to stay with a Cuban family in a licensed casa particular. Make reservations well before arriving in Cuba—but don’t expect your reservations to be honored (except at casas particulares).

Cuba’s strongest suit is its vibrant culture. The vast majority of visitors to Cuba come for the vivacious music and dance; the historic architecture; and, of course, a chance to experience life under the only Communist regime in the Western hemisphere before it all changes. Others are content sampling the beautiful beaches and bucolic landscapes. For active travelers, bicycling, horseback riding, scuba diving, and sportfishing are the most developed pursuits. Ecotourism is only now beginning to be developed and facilities and knowledgeable guides are few and far between.

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WHEN TO GO

Cuba has fairly distinct seasons: a relatively dry and mild winter (November–April) and hot and wet summer (May–October). Early spring is the ideal time to travel, especially in the Oriente (the eastern provinces), which can be insufferably hot in summer. Christmas and New Year’s are the busiest periods, and many accommodations and car rental agencies sell out during this period, while finding a domestic flight is near impossible. Hotel prices are usually lower in summer—the low season (temporada baja)—when hurricanes are a slim possibility. Tropical storms can lash the island even in winter, however.

You might want to time your visit to coincide with a major festival, such as carnival in Santiago de Cuba, or the Festival of New Latin American Cinema in Havana.

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WHAT TO TAKE

Dress for a tropical climate. Pack items that work in various combinations—preferably darker items that don’t show the inevitable dirt and stains you’ll quickly collect on your travels (Cuba’s laundry and dry-cleaning services are untrustworthy). However, dark clothes tend to be hotter than khaki or light-colored clothing. White T-shirts are perfect for reflecting the harsh sunlight. A pair of cargo shorts or pants and a photographer’s jacket with heaps of pockets is handy.

Pack a warm sweater and a windbreaker for winter visits, as brief spells of cold weather can occur. Eschew a raincoat for a breathable Gore-Tex jacket. A small umbrella is also a good idea at any time of year (they’re almost impossible to find in Cuba, so bring your own). In summer, the weather is hot and humid: You’ll want light, loose-fitting shirts and shorts. Knee-length shorts for men are acceptable almost everywhere. Save your shorter running shorts for the track. For longer visits, pack a regular change of socks and underpants. Wash them frequently to help keep athlete’s foot and other fungal growths at bay. Denim jeans and other thick cottons take forever to dry when wet, so light cotton/polyester blend clothes are preferred; they’re cooler and dry quickly. Ideally, everything should be drip-dry, wash-and-wear.

Cubans are fastidious about dressing well, especially when going out to the theater or dinner, and for business functions. You may wish to take a dress jacket or cocktail dress for dinners in more expensive hotel restaurants, and for that unexpected meeting with Fidel. However, most Cubans dress informally, though neatly, for all occasions.

Two T-shirts plus two dressier shirts (including a guayabera), a sweater, photographer’s jacket, pair of jeans, cargo pants, lightweight sweatpants, two pairs of shorts, and a pair of dress pants suffice for me. Women may wish to substitute blouses and mid-length skirts. Don’t forget your bathing suit.

A comfortable, well-fitting pair of sneakers will work for most occasions. Pack a pair of dress shoes for your evening ensemble. You’ll want lightweight canvas hiking boots with ankle protection for hiking muddy trails in the mountains.

Take all the toiletries you think you’ll need, including some toilet paper, a towel, and face cloth. Bring any specific medications you think you’ll need. If you bring prescription drugs, be sure the druggist’s identification label is on the container. Women should pack extra tampons.

Writing materials are hard to come by; take pens, pencils, and notepads (these make great gifts for children). An English/Spanish dictionary is handy and makes a good parting gift.

Space on buses and planes is limited. Limit yourself to one bag or suitcase, plus a small daypack and/or camera bag. Avoid backpacks with external appendages; they catch and can easily break. A small daypack allows you to pack everything you need for a one- or two-day side-trip and leave the rest of your luggage in storage at a Havana hotel. However, do not leave items in exterior pockets, and always ensure that your bag or suitcase is securely locked.