Even though this is a Caribbean country, you should always bring some kind of warm clothing (a light shawl or hooded sweatshirt) appropriate for frigid, air-conditioned cars and buses. From September through November, be sure to have a good and strong folding umbrella.
If you'll be spending time in Santo Domingo, you'll find that residents dress up more. Women, in particular, dress up every day; high heels are the norm, and women never wear sneakers, flip-flops, or shorts, always a dress, skirt, or slacks and stylish shoes (more often with 3"-6" heels). In fact, some museums and churches will not allow tourists to enter if they're wearing skimpy tops or shorts. Similarly, men will find that a guayabera shirt will take them anywhere, but Dominican men never wear shorts or flip-flops, reserving those for the beach. In offices and in fine-dining restaurants, it's not unusual to see white starched shirts, ties, and dark suits. Younger Dominican men may wear designer jeans and polo shorts. And the tropical fedora is back in style, with girls and some of their dates, wearing the smaller version of these Panama hats. But the more casually you dress, the more you'll be sniffed at as a turista.
The North Coast is typically cooler and windier, particularly from December to March. At night you'll want long sleeves and perhaps even a jacket. Along the Southeast Coast and in Punta Cana, the weather is warm year-round, but you may still want something to protect yourself from the chill of nighttime air-conditioning.
If you're going to the mountain areas such as Jarabacoa, Constanza, or Valle Nuevo, you must be prepared for chilly weather at night because of the elevation. In Constanza and Valle Nuevo in the winter you will need hats, ski parkas, gloves, and scarves. In the hilly parts of the Southwest temperatures are not as cold, but they certainly drop at night, when winds pick up. But during the day it can be unbearably hot.
Generally, public restrooms in the Dominican Republic are unsanitary and do not have toilet paper. Always pack small tissue packets, travel-size wipes, and hand sanitizer.
If you'll be shopping for groceries, bring a tote bag; plastic bags at supermarkets and drug stores tear easily, as they are poor quality, when they're available at all.
Cosmetics and toiletries, sunscreen, and mosquito repellent are difficult to find if you want the usual American brands, and they are much more expensive than in the United States (expect to pay two to three times what you would normally pay). Over-the-counter medications, baby formula, disposable diapers, tampons, and contact lens supplies are similarly expensive, and sometimes you have to try several shops. (Major supermarkets such as Nacional, or the California department store(s) carry most of these things).
Bring earplugs. The Dominican Republic may be the noisiest country that you've ever visited. In addition to the constant honking and incessant drone of the motorcycles, there's always high-volume Dominican music. By night, the music at the colmodons (general stores/bars) can be heard for a mile. And earplugs are almost impossible to buy in the Dominican Republic. Of course, an iPod can also help you drown out your surroundings.
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