Decide when to travel. Because Jamaica has a tropical climate, you can expect year-round hot and humid weather. Planning your trip so that you avoid the two rainy seasons of the year is advisable; Jamaica's rainy seasons are from May to June and September to November. Additionally, from June to September the island may be prone to more hurricanes than at other times of the year.
Plan where to stay. Portland has many places to stay, none more varied than in the capital, Port Antonio. Here you will find cottages, houses, apartments, hotels and villas. Determine what your needs are and what your budget is, and decide where you would like to stay in Portland.
If you're looking for beachfront, head for a villa or cottage. If you're planning to stay inland a bit and would like more of a homey feeling, find an apartment or house to rent. The website See Jamaica Cheaply (see Resources) has options in all these categories.
Plan what to do. Portland features countless things to see and do, so you'll have to narrow down what is most important to you to see, then try to get to as much else as possible. See the famed Rio Grande on a river tour. Sample the famous Jamaican jerk chicken at its birthplace in Boston Bay. Go to Long Bay and rent a surfboard at the best surf spot in Portland. Tour the Blue Mountains. Get your Jamaican public beach experience at the famed Winnifred Beach. Take a trip to the tranquil Somerset Falls, then travel to the large waterfalls made famous in the movie "Cocktail" at Reach Falls.
Plan on spending quite a bit of time in Port Antonio, as it features the most to do and see in one concentrated area. Take a trip to Musgrave Market, which can be tricky to find but is worth it for a large outdoor market selling everything from fruits and vegetables to clothes to cooked food. Also in Port Antonio is the Village of St. George, a shopping mall built in the style of European architecture. Georgian, Gothic, Tudor and art deco styles are represented.
