When to Go

High season runs from mid-December through mid-April. Winter hotel rates are as much as 25% higher than off-season rates, and hotels tend to be packed. San Juan is also a commercial town, and hotels, except for the short season around Christmas and New Year's, are busy year-round with international business travelers. This doesn't mean the island won't have rooms in winter -- rarely is space completely unavailable -- but if you plan to beat that winter sleet in Duluth, make arrangements for flights and hotel space at least a few weeks ahead of time. A fun and often less expensive time to visit is during the "shoulder" seasons of fall and spring. The weather is -- still -- perfect, and the tourist crush is less intense.

You can always visit Puerto Rico during the less busy summer season, when temperatures are hot and hurricanes more likely. And you might even find some added bargains at this time of the year. Given its proximity to the East Coast of the United States and relatively large number of flights, Puerto Rico can be an excellent hurricane-season option for the Caribbean. This kind of trip works best when you can visit at the last minute, when you'll be able to watch the weather report and know a hurricane isn't about to strike; it's also nice if you can get a bargain airfare, which might very well happen on a summer weekend. Know that business travel -- not to mention the fact that San Juan serves as a major hub for American Airlines flights to the rest of the Caribbean -- keeps the flights to Puerto Rico fairly full from Monday through Friday all year long.