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For a lot of us battling the blistering cold of winter year after year, the lush countries surrounding the Caribbean call to us like a siren song... or wedding bells! Whether you're looking for a winter wedding with sand instead of snow or curious about when to find the best destination wedding deals, here's everything you need to know about some of our top destinations to say, "I Do."

Dominican Republic

Photo: Ambrogetti Ameztoy

Best Weather

March through May. The temperatures stay below 85 during these drier months, so the air has little humidity and the sun is bright and shiny. Similar idyllic weather is found from December to February, but keep in mind that many other travelers have the same idea of escaping the cold, so anticipate escalated hotel costs during this time.

Most Affordable Time

March through November. Though least expensive, the months of June through to November are also hurricane season, so expect a lot of rain and potentially dangerous winds. To achieve the best weather for the best price, March through May are your ideal travel months in the Dominican Republic.

Liveliest Time

February holds the honor of being the month of the Dominican Carnival.  Across the nation, cities come alive every weekend with parades in vibrant celebration of the historic Carnival. Parade-goers wear ornate masks and extravagant costumes to represent different characters within their culture, making the festivities quite a sight to behold. Later in the day, there is local street food and music to be enjoyed as the parades turn into energetic parties. If you’re staying in Punta Cana and are willing to make the almost four-hour trek to La Vega, you will be delighted by the largest celebration of Carnival. Or if you’d like the experience, but a quicker drive, head over to the Parade on Malecon in the old world capital of Santo Domingo.


Jamaica Destination Wedding Bridesmaid Photography

Photo: Defining 78

Best Weather

November through March. These months boast the most comfortable temperatures the island sees between 75 and 85 degrees, as well as the least precipitation of the year. Go any other month and you can bet it will be much hotter and rainier.

Most Affordable Time

Between April and October, hotels in Jamaica offer some sweet incentives for staying, but the rain could put a damper on your beach time. For ideal weather at an affordable price, your best bet is to travel between November and December but avoid the weeks surrounding Christmas as rates tend to skyrocket during this peak period.

Liveliest Time

February. As one might expect, Bob Marley is a legend in Jamaica.  That’s why February is dedicated to his memory, celebrating his birthday and his extraordinary impact on the island. There are many festivals across the cities in his name, featuring food, drink, and (you guessed it) plenty of reggae music.

Costa Rica


Photo: Stories Wedding Photography Costa Rica

Best Weather

December through April. Late winter to early spring marks the dry season for Costa Rica, which is when the exotic wildlife is easiest to find and the beaches are most pristine. It’s also coolest during this period, with temperatures rarely reaching 80 degrees and the humidity at a minimum.

Most Affordable Time

May through November. Being blanketed by rainforests, it’s no surprise that Costa Rica has a long and very wet rainy season.  Some months even see over 12 inches of rain on average. With this, there are often fewer tourists and therefore greater deals for travel to the region.  Beyond saving some dollars, traveling during these months also places you in the middle of the “green season” with no shortage of impeccable views of the dense, lush forests. Plus staying in less-affected areas like Guanacaste means rain will only bother you for a few hours a day rather than your whole trip.

Liveliest Time

October. Another Caribbean Carnival you have to experience at least once, Limón Carnival commemorates the arrival of Christopher Columbus in 1502 to their tropical shores. It is dressed with local delicacies, music, dancing, parades, and brightly-colored costumes in celebration of the Afro-Caribbean heritage so meaningful to the culture. It’s a spirited and joyous event that even lands in a mini dry season to ensure the show may go on.

St. Lucia


Photo: Caricom Caribbean Community

Best Weather

December through June. The driest months of the year, December through June also have the best temperatures ranging from about 83 to 87 degrees. The nice temps bring with them cool breezes that help curb the heat, while still feeling nice and toasty.

Most Affordable Time

May through November. With the arrival of devastating hurricanes this season, the potential risks when traveling to the eastern Caribbean during these times are clear. Therefore while it can be very cheap to travel to St. Lucia from July to November, for only slightly higher rates, you can also go between May and June to avoid hurricane season altogether. Plus you’re almost guaranteed more beach time and sunny days during these less rain-ravaged months.

Liveliest Time

The St. Lucia Jazz & Arts Festival, held in May every year, is a time-honored event spanning nearly three decades. It is a week-long festival featuring an array of musical talents playing jazz, R&B, soul, pop, reggae, and soca amidst other food and fashion events. The main concert takes place on the beautiful national landmark of Pigeon Island so you can appreciate the natural beauty while taking in the sounds of St. Lucia.

When is the best time to fly south for your wedding?  Anytime, really!  When it comes down to it, it’s up to you how hot or cool you’d like it to be, how many festivals or events you want to take part in, or how much you’d prefer to have you and your guests spend on your vacations. Reach out to our Groups Team to get started planning your special day!

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