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When you plan a trip to the Caribbean, you can expect to encounter lots of talk about seasons: The Season (holiday season), high season, low season, shoulder season, and hurricane season. For a place where the leaves don't change and the temperature rarely budges more than a few degrees either direction from around 80 degrees Fahrenheit, you'll hear the word season tossed about an awful lot. All the Caribbean islands have similar seasons with slight weather variations.
 | The reason seasons matter in the Caribbean has virtually nothing to do with the weather and everything to do with your room rate. For example, published room rates for a resort may include as many as a half-dozen different prices listed for the exact same accommodations. What you pay depends on exactly when you visit; timing is everything when it comes to a Caribbean vacation. |
Generally, seasonal differences break down something like this, but keep in mind that they have lots of variations:
- Holiday season (also known as The Season): December 15 to January 3
- High season: January 4 to April 14
- Shoulder season: April 15 to May 30 and September 1 to December 14
- Low season: May 30 to August 31
- Hurricane season (overlaps with shoulder and low seasons): June 1 to November 30
Holiday season and high season
The Caribbean's high season heats up right before Christmas and lasts through mid-April. During the holiday season, referred to on the upscale islands as simply "The Season," longtime guests often snatch up reservations for the best lodgings years in advance. At Christmastime, Jamaica's exclusive Round Hill once turned away James Bond — er, Pierce Brosnan. So, if you're going to a resort in Barbados or the British Virgin Islands (BVIs) around the holidays, be prepared to make your plans well in advance.
 | The better hotels often have minimum-stay requirements in effect during the holiday season and stringent cancellation policies. If you plan a trip during the holidays, make your reservations as early as possible, expect crowds, and plan to pay top dollar for everything. |
In-season advantages
If you live in northern climes that are swept with wintry blizzards, nothing is more appealing in brutal February than visions of a white sandy beach, a brilliant sun, and a palm tree-studded Caribbean island. Here are a few advantages of fulfilling that desire:
- The winter weather in the Caribbean is considered as close to perfection as anywhere on the planet. The temperature rarely dips below 70.
- All restaurants, services, sports activities, entertainment, shops, and facilities operate at full blast from mid-December to mid-April.
- The timing is ideal for singles and honeymooners because families with children are gone and a more romantic atmosphere prevails.
- Both the rainy season and the hurricane season are over. You mostly have sand, sea, and sunshine.
- The cuisine at resorts is better than ever. Top chefs from both Europe and America are brought in during the winter months to tempt your palates.
In-season disadvantages
Of course, vacationing in the Caribbean during the in-season does have a downside:
- You'll have to get used to people crowding you in airport lounges, on the most popular beaches, at the all-inclusive resorts, at groaning buffet tables, at the best restaurants, and in the casinos.
- If you plan a winter visit, reservations are vastly important — at resorts, car-rental agencies, nightclubs, the best restaurants, and even scuba-diving courses.
- Hotel rates peak in-season, especially around the Christmas holidays. You'll pay top dollar for everything, from your bedroom to your car rental. Nothing, not even merchandise in shops, is reduced in winter.
- Personalized service goes the way of the trade winds.
Shoulder season
In the shoulder seasons — late spring and the fall — prices are sometimes slightly reduced. Shoulder season is ideal if you want to go at a quiet time, because children are in school and few families are on the islands.
This rule has an exception, however: Between the Easter holidays and spring break, April is an extremely tough and expensive time to book a vacation on Puerto Rico. You may also have difficulties booking in Aruba, Montego Bay and Negril (Jamaica), and St. Thomas (U.S. Virgin Islands) at this time.
| Some smaller resorts and restaurants close for repairs and maintenance in July, August, September, or October. |
Low season
If you come during the low season, rates drop like an anchor. Rates decrease as much as 60 percent in June, July, and August, making even some of the more exclusive resorts affordable. Travelers often make the assumption that because the Caribbean is so deliciously warm in the winter, it must be searingly hot in the summer. (That's not the case.)
You see lots of kids during low season — especially from Europe. On some islands, several hotels and resorts band together with the tourist boards during the summer months to offer super deals for families and honeymooners.
 | In the last few years, the Caribbean has finally begun convincing people that it's a year-round destination. Despite that self-promotion, finding a hotel room in the low season is pretty easy. Booking your flight, however, may not be as simple. Many nationals go home to visit during the summer — flights to Jamaica are especially full. And Europeans, who have much longer vacations than Americans, frequent the Caribbean in summer months. Reserve your flight as soon as you pick your destination. |
Tropical storms can kick up quickly in Caribbean summers, but they usually pass just as fast, leaving brilliant blue skies in their wake.
Off-season advantages
You'll enjoy the following if you go in the off season:
- A less-hurried way of life prevails. You have a better chance to appreciate food, culture, and customs.
- Swimming pools and beaches are less crowded — perhaps not crowded at all.
- Resorts offer amenities, which may include snorkeling, boating, and scuba diving, year-round — often at reduced rates off season.
- Resort boutiques often feature summer sales.
- You can often appear without a reservation at a top restaurant and get a table.
- The endless waiting game is over: no waiting for a rental car, tee time, or tennis court.
- Some package-tour fares are as much as 20 percent lower, and individual excursion fares are also reduced between 5 and 10 percent.
- Accommodations and flights may be easier to book.
- The very best of attractions — sea, sand, and surf — remain undiminished in the off season.
Off-season disadvantages
Summer travel has its drawbacks:
- You may be staying at a construction site. Caribbean hoteliers save serious repairs and major renovations until the off season.
- Hotels and resorts may be operating with reduced staffs, so services are often reduced.
- Not all restaurants and bars are fully operational at resorts.
Hurricane season
Part of the Caribbean's low season dovetails with the hurricane season, which officially runs from June 1 to November 30, with September being the peak time for a hurricane to hit. Of course, the rainy season also mirrors hurricane season, though it doesn't last as long on some islands. Fortunately, in the tropics, rainstorms typically pass over rapidly.
You will find the best bargains during hurricane season, and the odds are in your favor for good weather. Of course, you have no guarantee, and good odds won't make you feel better if you're the one being sent packing by the storm.
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