Planning a destination wedding in the Caribbean? After coordinating over 200 beach ceremonies across the islands, I can tell you the real costs vary dramatically depending on when you book. Most couples come to me thinking June weddings are cheaper—they’re not. The Caribbean pricing model is counterintuitive, and understanding it can save you $15,000 or more.
Here’s what I’ve learned: Your wedding date affects everything from venue fees to flight costs for your 50 guests. The difference between a February wedding in Turks and Caicos versus an August one? About 40% in total costs. Let me break down exactly what you’re looking at, month by month, based on actual weddings I’ve planned.
January Through March: Peak Season Premium Pricing
Look, everyone wants perfect weather, and that’s exactly what January through March delivers. But here’s the reality—you’re paying top dollar for that guarantee. During these months, I’m seeing average wedding packages starting at $45,000 for 50 guests, and that’s before you add any customization.
Resort venues jack up their rates by 30-40% during this period. The Ritz-Carlton in Grand Cayman? Their beach ceremony fee jumps from $3,500 to $5,000. Your guests’ rooms that cost $350/night in September are now $650. What kills most budgets isn’t the ceremony cost—it’s accommodating your guests. A destination wedding planner becomes essential during peak season because we have relationships that can knock 15% off those inflated room blocks.
The hidden cost nobody mentions? Vendor availability. That photographer you loved? Booked solid. The steel drum band? They’re charging surge pricing. In my experience, couples need to budget an extra $8,000-12,000 just for the peak season markup. The upside? Weather is virtually guaranteed—I’ve had exactly two rain delays in 15 years of February weddings.
April Through June: The Smart Money Window
This is where savvy couples win big. April through early June offers what I call the “golden ratio”—great weather probability at 25-30% lower costs. We’re talking $32,000-38,000 for the same wedding that costs $45,000 in February.
Here’s what actually happens in these months: Resorts are transitioning from high to low season, so they’re motivated to fill rooms. I recently negotiated a deal at Sandals Montego Bay where the couple got every 5th room free for their group. That saved them $7,500 right there. The weather? Still fantastic through May. June gets slightly more humidity, but nothing that ruins hair or makeup.
The real advantage comes with vendor flexibility. That same photographer charging $5,000 in March? They’ll take $3,500 in May and throw in the rehearsal dinner coverage. Musicians, florists, even the officiant—everyone’s negotiating. If they’re not discussing shoulder season advantages, find someone who will.
July Through August: Hurricane Season Gambling
Let me be straight with you—July and August are cheap for a reason. We’re talking 40-50% savings, but you’re rolling the dice on weather. I’ve planned 30+ summer weddings, and while only three got seriously impacted by storms, the stress factor is real.
Budget-wise, you’re looking at $25,000-30,000 all-in for 50 guests. Resorts like Beaches Turks and Caicos drop their rates to $275/night from their winter peak of $550. But here’s what nobody tells you—hurricane insurance for a wedding runs $2,500-4,000, and most couples skip it. Bad move. I watched one couple lose $18,000 when Hurricane Dorian hit.
The upside? Total vendor flexibility and premium upgrades. That basic package suddenly includes top-shelf liquor, the presidential suite, and sunset catamaran tours for your guests. Hotels are so eager for business that I’ve negotiated deals including free spa treatments for the entire wedding party. If you’re willing to risk it and buy proper insurance, August particularly offers incredible value. Just know what you’re signing up for.
September Through November: The Industry Secret Season
Here’s what most destination wedding planners won’t advertise—September through November is actually brilliant for specific islands. Aruba, Barbados, and Curacao sit outside the hurricane belt, yet their prices drop 30% because tourists assume all Caribbean islands are risky.
I’m consistently booking full weddings in Aruba for $28,000-32,000 during these months. The weather is actually more predictable than April, and you get the entire resort’s attention. One couple I worked with in October basically had a private resort experience at the Hyatt Regency Aruba—85% of the property was available for their guests.
The trick is choosing your island strategically. Bahamas in October? Risky. Southern Caribbean? Golden. Vendors in these locations know their competitive advantage and price accordingly—not dirt cheap like hurricane zones, but very reasonable. Flight costs also crater during this period. Your cousin flying from Seattle? Their ticket just dropped from $800 to $400. When you multiply that by 50 guests, the savings are substantial.
December: The Wildcard Month Pricing
December is the strangest month for Caribbean wedding pricing—it’s actually two different months from a cost perspective. December 1-20 offers some of the year’s best values, while December 21-31 is astronomical. I’m talking about a $20,000 swing for the same exact wedding package.
Early December weddings run $30,000-35,000, and resorts are surprisingly flexible. They’re trying to fill rooms before the holiday rush, and weather is consistently excellent. I booked a wedding at Secrets Cap Cana on December 10th last year—the couple saved $12,000 versus the same package on December 28th. But here’s the challenge: Guest attendance drops 30% for early December dates. People are holiday shopping, kids are in school until mid-month, and work parties compete for attention.
Late December? Forget it unless you have unlimited budget. Minimum stays jump to 7 nights, room rates triple, and every vendor charges holiday premiums. The only December weddings I recommend are December 5-15, when you get good weather, decent prices, and avoid the holiday chaos entirely.
Conclusion
After 15 years in this business, here’s my take: The “perfect” month for your Caribbean wedding depends entirely on your priorities. If weather certainty and guest convenience matter most, bite the bullet and pay for February or March. If you’re budget-conscious but risk-averse, April and early May are your sweet spots. Adventure-seekers with good insurance should absolutely consider August in hurricane-safe zones.
The biggest mistake couples make? Choosing their date before understanding these cost dynamics. A good destination wedding planner will walk you through a month-by-month analysis specific to your chosen island. We know which resorts offer the best shoulder season deals, which vendors are flexible, and exactly how to maximize your budget regardless of when you choose to say “I do.”
Remember, your wedding date is one of the few decisions you can’t change once deposits are down. Take the time to understand not just the sticker price, but the total cost including guest accommodations, vendor premiums, and weather insurance. The right month choice can mean the difference between your dream wedding and settling for less.
What’s the average cost for 50 guests?
Realistically, budget $30,000-45,000 depending on your chosen month and island. Peak season (January-March) averages $42,000, while hurricane season (July-September) drops to $28,000. These figures include ceremony, reception, and group accommodations but not flights. Your destination wedding planner can usually negotiate 10-15% off published rates.
Which Caribbean island offers the best value?
Dominican Republic consistently delivers the best bang for your buck—think $25,000 for what costs $40,000 in Turks and Caicos. Aruba and Jamaica follow closely, offering all-inclusive packages that actually include everything. Avoid the Bahamas and St. Barts if budget matters. Each island’s value changes seasonally, so timing matters as much as location.
How far in advance should we book?
Eighteen months for peak season, 12 months for shoulder season, and surprisingly, 6-8 months for hurricane season can work. Earlier booking doesn’t always mean better prices—resorts release deals 10 months out. However, securing room blocks early is crucial. I’ve seen couples lose $8,000 because they waited and their guests booked rooms individually at peak rates.
Is hurricane insurance really necessary?
Absolutely for June through November weddings. Basic coverage costs $2,000-3,500 and covers non-refundable deposits if a named storm threatens your location. Skip the “cancel for any reason” upgrade unless you’re naturally anxious. Standard hurricane coverage is sufficient, and every destination wedding planner should insist on it for summer dates.
What hidden costs do couples forget?
Welcome bags ($30/guest), hair and makeup trials ($500), vendor tips ($2,000), marriage license and paperwork ($500), and airport transfers for guests ($150/person). These “forgotten” items typically add $5,000-7,000 to your budget. Also, international transaction fees on your credit cards can add up to $500 if you’re not using the right cards.
Should we visit before booking?
Yes, but strategically. Visit during your planned wedding month, not peak season, to understand real conditions. A three-day scouting trip costs $2,000 but saves you from $10,000 mistakes. Some resorts offer free planning trips if you book. Your destination wedding planner can often virtual tour effectively, saving you the preliminary trip expense.
How many guests typically decline?
Expect 35-40% decline rate for destination weddings, though December and hurricane season push this to 50%. Peak season and long weekends see better attendance—around 25% decline rate. Budget for 20% more guests than you want, knowing natural attrition brings you to ideal numbers. Geographic clustering affects this significantly.
What’s included in all-inclusive packages?
“All-inclusive” is misleading. Basic packages cover ceremony space, standard flowers, basic cake, and dinner reception. Premium alcohol, photographers, entertainment, and décor upgrades cost extra. Real talk: Budget another $10,000-15,000 beyond the base package for the wedding you’re actually envisioning. Resorts showing $5,000 packages deliver $5,000 weddings—nothing more.
Can we legally marry in the Caribbean?
Yes, but requirements vary wildly. Jamaica needs four days residency; Turks and Caicos needs 24 hours. Document requirements range from simple (passport and birth certificate) to complex (single status affidavits, apostilled documents). Many couples legally marry at home and do a symbolic ceremony. This saves $500-1,500 in paperwork and translation fees.
Which resorts are actually worth it?
After 200+ weddings, my consistently excellent experiences: Sandals and Beaches (predictable quality, great coordination), Secrets and Dreams (adults-only luxury that delivers), and Iberostars (exceptional value). Avoid boutique resorts unless you have an experienced destination wedding planner—they’re beautiful but often logistically challenging. The Four Seasons never disappoints but prepare for premium pricing even in low season.
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