Dress for a tropical climate. Pack items that work in various combinations. White T-shirts are perfect for reflecting the harsh sunlight. A pair of shorts or pants. 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. Don’t forget your bathing suit.
You may wish to take a dress jacket or cocktail dress for dinners in more expensive hotel restaurants. However, most Cubans dress informally, though neatly, for all occasions. 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.
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 Casa Particular.