Planning a Caribbean vacation doesn't end with picking an island: You also need to figure out when to take your vacation. The best time to visit the Caribbean is from October to mid-December when the weather is sunny and the hotel rates have yet to increase for the peak tourist season. If you have more flexibility with your schedule, every month brings unique events and festivals that you'll want to factor into your trip planning. Read on for your ultimate guide to scheduling your next visit to the Caribbean.
Weather in the Caribbean
Thanks to trade winds that keep many of the islands cool, the weather in the Caribbean is sunny and delightful year-round. The dry season reliably occurs during the winter months, from December through March, making it the perfect time for northern snowbirds to book flights down to the tropics. The rainy season begins in the summer months, and the chance of tropical storms and hurricanes increases through early fall. Travelers looking to visit during hurricane season should consider purchasing travel insurance.
Peak Tourist Season in the Caribbean
The rates of hotels and airfare vary drastically based on the time of year you are visiting. The peak tourist season begins in mid-December and concludes in mid-April, after the last of the spring break visitors have boarded their flights home. Travelers looking to visit the Caribbean during the colder months should plan to book their travel well in advance in order to save money and to monitor for flight and hotel deals in the months preceding their vacation.
Key Events in the Caribbean
Visitors should consider visiting during Carnival, which occurs at different time periods on each island. It's both a holiday festival and celebration of national pride. There are pageants, J'ouvert music (calypso-type music), food fairs, and street parties.
The few weeks before Christmas are filled with bargain rates on hotels and airfares. Many resorts cater to families looking to spend the holidays together, and it's easy to find local Christmas celebrations regardless of where you travel. Holiday cruises to the Caribbean are very popular.
Events to check out:
- St. Nicholas Day: This day is celebrated on December 5th in the Dutch Caribbean, which comprises of Curaçao, Aruba, St. Maarten, Bonaire, St. Eustatius, and Saba.
- Junkanoo Festival: A celebratory parade and party across the Bahamas, Junkanoo festivals take place on Boxing Day and New Year's Day. The largest party parades are in Nassau, but you can also experience the intoxicating carnival atmosphere on Grand Bahama Island, Eleuthera & Harbour Island, Bimini, the Exumas, and the Abacos.
- New Year's Day: Parades are the order of the day in the Key West and St. Kitts, where the streets are full of revelers long into the evening.
- Bob Marley Day: Jamaica celebrates the life and music of Bob Marley on his birthday (February 6) each year.
- St. Kitts celebrates from Christmas until New Year's (mid-December through January 2).
- Aruba, Curaçao, and St. Kitts all celebrate the annual tradition throughout January.
- St. Martin, Jamaica, Curaçao, St. Barts, Martinique, Trinidad, and Dominica are among the islands celebrating Carnival in February.
The weather is dependably warm and dry in March, and a lot of people head to the islands over Spring Break. The Caribbean is a very Catholic region, so you'll see a great number of celebrations and parades over the Easter holiday.
You’ll have mostly sunny days and comfortable, moderate temperatures in April—but if you can wait until the end of the month (the “shoulder season”) to book your trip, you’ll also save money and avoid the Spring Break crowds.
Come May, there's no threat of hurricanes, resorts offer great rates and last-minute bargains, and there are plenty of events and festivals designed to entice visitors.
Events to check out:
- FLOW Oistins Festival: Barbados holds this annual celebration during Easter Weekend. The street fair includes cuisine such as fish cakes, fried fish, and head cheese.
- A Taste of St. Croix: The U.S. Virgin Islands celebrates its unique and diverse cuisine at this one-day fundraiser event that draws some of the island's best chefs.
- The Tobago Jazz Experience: This three-day concert attracts some top international acts to the typically sleepy island. Past headliners include Diana Ross and Rod Stewart.
- St. Barth Film Festival: Celebrities flock to St. Barth at the end of April for the five-day celebration of Caribbean film.
- The Grenada Chocolate Festival: This nine-day event celebrates everyone's favorite confection. The dates vary year-to-year, but it's typically held from late May into June.
- St. Maarten Carnival: St. Maarten touts their Carnival celebration touts as the "biggest and best" in the northern Caribbean. The celebration runs from the end of April through the first week of May.
- Regattas: The Caribbean hosts many regattas throughout the year, but these exciting sailing events are especially prevalent in the spring.
- The St. Thomas International Regatta takes place in March. This is one of the world's best competitive yacht races and is based at the St. Thomas Yacht Club, with major social events at the Ritz-Carlton St. Thomas.
- Antigua Sailing Week is the biggest regatta in the region; it runs from late April to early May.
- Les Voiles de Saint Barth takes place mid-month.
Low-season rates in June, July, and August are the biggest attraction. Plus, you'll experience warm, mid-summer temperatures throughout the region, including the Bahamas and Bermuda. Keep in mind that the northern latitudes may be experiencing some cooler days and evenings in June, and hurricane season starts heating up in August.
Events to check out:
- Anguilla Summer Festival: This annual tradition features boat races, beach parties, and parades, with lots of delicious food, exuberant music, and pageantry to fuel the fun.
- Aruba International Regatta: Sailors from around the world come to the island to race all manner of watercraft, from yachts to sunfish to miniature boats and even stand up paddle boards.
- Caribbean Fashion Week: Usually taking place in mid-June, this week-long fashion event is held at the National Arena in Kingston, Jamaica each year.
- Portland Jerk Festival: Jamaican jerk flavored foods have become popular worldwide, and in July you can get mouthwatering jerk chicken, pork, sausage, and more at this annual festival in Jamaica.
- North Sea Jazz Fest Curaçao: This event closes out August with some of the hottest names in music. Performers like Prince, Rod Stewart, Alicia Keyes, Stevie Wonder, and John Legend join the island's best homegrown talent for three days of nonstop entertainment.
- Barbados throws the largest Carnival celebration in the region with Crop Over. This five-week-long festival is filled with music, dance, drinks, and plenty of cultural events and performances throughout the summer in celebration of the harvest.
- Bermuda starts the festivities in June over Heroes' Weekend and continues the celebrations into July.
- Antigua celebrates its Carnival in July.
Visitors to the Caribbean in the fall will enjoy off-season prices, uncrowded resorts and beaches, and generally great weather (although things begin to cool in the northern latitudes). November is especially a good time for airfare deals. Renting a villa in the Caribbean has become a popular option for Thanksgiving celebrations by far-flung families, and cruise lines also offer special Thanksgiving cruises.
Events to check out:
- Belize Independence Day: Celebrations begin on St. George's Caye Day on September 10 and end on September 21, Independence Day. Expect flag-raising ceremonies and street parades.
- Belize Carnival: The annual Carnival is held in September in Belize to showcase music, theatre, fashion, and dance.
- Bermuda Sand Sculpture Competition: Witness artists from all over the world build unbelievable sand structures in Horseshoe Bay Beach in Bermuda.
- Bonaire International Sailing Regatta: This long-running (and week-long) regatta features races close to the coast of Bonaire. The festival itself features a street carnival and many events for sports fans, including softball, beach volleyball, and even a dominoes tournament.
- World Creole Music Festival: Held at the end of October, this is the highlight of sleepy Dominica's annual cultural calendar with Creole music like cadence-lypso, Kompas, zouk, soukous, bouyon, and even Louisiana zydeco.
- Pirates Week: This annual event in the Cayman Islands celebrates the nation's cultural heritage and pirate legends. Spectators are treated to parades, fireworks displays, street dances, and costume contests.
- The Barbados Food and Rum Festival: This festival is a series of culinary experiences with acclaimed chefs, rum experts, and mixologists. There are food and rum pairing events, plus a beach party at the Hilton Resort Barbados.
- Mojito Fest: Enjoy unlimited mojitos, food samples from local restaurants, and live music at this festival in Puerto Rico.