Congratulations, you're engaged! If you're dreaming of saying "I do" on a beach, you're probably asking the same question couples ask us every week: what do we decide first?
The good news is that you don't need to decide everything at once. Here are the first few decisions, in the order we'd make them, so you can start planning with a clear head instead of a hundred open browser tabs.
How far ahead should we start planning a destination wedding?
Most couples we work with first reach out about 14 months before their wedding, and most book within about a month of that first email. That timing works well for a reason.
Some group pricing for destination weddings is available about 18 months ahead, and most of our couples secure their group space 14 to 16 months out. Starting 14 to 18 months out gives you the widest choice of resorts, dates and ceremony venues, and gives your guests time to plan and save.
Can it be done faster? Yes. Our shortest booking so far was 101 days out, with every payment completed by the 90-day mark. It's possible, but you'll have fewer choices. Our post on planning a last-minute destination wedding covers what to expect.
Thinking about 2028? You're not too early. We already have a wedding group booked for 2028.
First decision: pick your month and destination
Before you fall in love with a resort, choose roughly when and where. Your month shapes the price, the weather and how easily your guests can get time off work. Your destination shapes which flights your guests can take from home.
For our couples, the most popular wedding months are January, February, April and November. Many like the idea of a winter escape with everyone they love.
The destinations our couples choose most are:
A few questions to ask yourselves:
- Where do most of our guests live, and which airports will they fly from?
- How long a flight are our guests willing to take? Direct flights are seasonal from some cities, so check before you decide.
- Would we rather have a short airport transfer, or is a longer drive worth it for the right resort?
- Does our month fall in hurricane season? We'll cover choosing your date around it in a future post.
Second decision: set a realistic budget for your guests
This is the step that surprises couples most. Many come to us with a guest budget that is lower than what a week at an all-inclusive resort really costs, so it helps to know the starting point early.
For 2027 weddings, the travel portion for a seven-night trip is usually between $2,200 and $2,700 per person in Canadian dollars, depending on where your guests fly from and where you're going. For a closer look, read A Realistic Budget for Guests at Your Destination Wedding.
Three things move your guests' budget the most:
- Kids or no kids. At least 60% of our couples already have children, and about 80% choose a family-friendly resort. The other 20% choose adults-only. Deciding early narrows your resort list fast.
- Guest count. Our wedding groups have ranged from 14 to 109 guests, and most fall between 40 and 80. A rough number helps us match you with resorts that suit your group size.
- How your guests book. We book Canadian tour-operator packages that include flights from each guest's home airport, the resort and airport transfers. In our experience, room blocks where guests book their own flights usually cost them more.
You don't need exact numbers yet. A rough guest count and a comfortable price range for your guests is enough to start comparing resorts.
Third decision: legal or symbolic ceremony
Most of our couples choose a symbolic ceremony at the resort and marry legally in Canada before the trip. It keeps the paperwork simple and lets the beach ceremony be all about the celebration.
A legal ceremony abroad is possible, but the document rules vary by country. Check the entry and document requirements at travel.gc.ca and with the resort's wedding team. We'll cover the full legal vs symbolic decision in our November 17 post.
Our advice
Don't start by picking a resort. Start with these four things: your month, your rough guest count, a comfortable price range for your guests, and whether kids are coming. Once you know those, the right two or three resorts usually stand out.
Then compare those resorts side by side, including each resort's wedding package and what your guests would pay from their home cities. That's exactly how we build our quotes, because a side-by-side view makes the choice much easier than flipping between websites.
Once these first decisions are made, our Destination Wedding Planning Timeline for Busy Canadian Couples walks you through what comes next, month by month.
With over 13 years of experience and 20 to 25 weddings a year, we handle the travel side from start to finish: guiding your resort choice, booking your guests, answering their questions and tracking their payments. Once you've chosen your resort, we connect you with the resort's on-site wedding coordinator for the ceremony details. Learn more about how we plan destination weddings and who we are.
Ready for the next steps after these first decisions? Tell Us About Your Wedding and we'll take it from there.
Quick FAQ
How far in advance should we book a destination wedding? We suggest 14 to 18 months ahead. Some group pricing is available about 18 months before the wedding, and most of our couples secure their group space 14 to 16 months out.
Can we plan a destination wedding in less than a year? Yes. Our shortest booking so far was 101 days out. You'll have fewer resorts and dates to choose from, so the sooner you start, the better.
Do we need to pick a resort before we reach out? No. Most couples come to us without a resort picked. Your month, guest count and guest budget are all we need to start.
How much will the trip cost our guests? For 2027 weddings, the travel portion is usually between $2,200 and $2,700 per person in Canadian dollars for seven nights, depending on where your guests fly from and where you're going.
Is there a fee to hire a destination wedding travel advisor? There's no planning fee for our service. The resorts and tour operators we book with pay us.
Let's start planning together
When you're ready, tell us your month, rough guest count and the places you're dreaming of, and we'll send you side-by-side resort options by email. There's no planning fee for our service.
Featured photo by Mony Mtz Photography, Cancún area.