Hotels on charge their highest rates during the peak winter season, from mid-December to mid-April. Christmas week rates may double those tariffs. You should make reservations months in advance for Christmas and February, especially over Presidents' Day weekend. School spring breaks are also busy family times.
The off-season runs roughly mid-April to mid-December (though exact dates vary according to the property). Even though August can be a popular month for vacationing Europeans, it's one big summer sale: Most hotels, inns, condos, and villas slash their prices 20% to 50%. The beaches are less crowded and many top lodgings and restaurants shutter for one, even 2 months as the owners take their own vacation or perform necessary renovations. Be sure to request a room away from noise if the hotel remains open during construction. I provide closing dates wherever possible, but visitors should double-check before booking.
High season features a temperate climate, rarely exceeding 90°F (32°C), with lower humidity and the famed cooling trade winds blowing in from the northeast. It's ideal beach weather, with the occasional cloudy day. Usually rain showers are brief: Islanders call them "liquid sunshine."
Rainy season runs from late May to mid-November. This doesn't mean it rains for days at a time or even every day. But this also roughly corresponds to the official Atlantic hurricane season, June 1 to November 30. Fortunately, satellite surveillance provides enough advance warning to take precautions and, rarely, evacuate.
Hurricanes -- The northeastern Caribbean has seen its share of destructive hurricanes; the latest to have an impact in this region was Hurricane Omar, which in 2008 eroded beaches and blew down beach shacks in the Maho Bay area in St. Maarten and also caused beach erosion on Anguilla's West End. Fortunately, modern technology and satellite surveillance provide plenty of advance warning for impending storms. Hurricane season officially begins in June and ends in late November, but high hurricane season in this neck of the woods is the month of September. A number of resorts use this time (early fall) to close for renovations, especially on St. Barts. If you are caught in a hurricane or tropical storm during your stay, follow the instructions of officials (especially in the event of an evacuation to higher ground). Keep in mind that low-lying areas may be prone to flooding, and the seas may have dangerous rip currents even after a hurricane has passed. For the latest satellite imagery and hurricane information, go to the National Oceanic and Atmospheric Administration's National Hurricane Center (www.nhc.noaa.gov).