Cruise or all-inclusive resort: which works better for a group?

Most trips around the Caribbean leave from Florida or another US port. From a Canadian city that usually means a connecting flight and a night in a hotel before the ship leaves, so nobody misses it if a flight runs late. The upside is that everyone reaches the port on their own. Your cousin can fly in from Calgary, the aunts from Halifax, on different airlines, arriving the day before if they like. A group spread across the country doesn't have to travel as one.

A sun destination is often nonstop from a Canadian city, which is a shorter, simpler trip with nobody overnighting near an airport. How good that service is depends heavily on where you fly from: Toronto, Montreal, Calgary, Vancouver, Ottawa, Halifax, and Winnipeg don't all reach the same places without a stop. Some operators also want most of the group on the same flight on the same dates, which quietly decides who can realistically come. Neither is a fault. They're different shapes of trip.

Room can often be set aside with very little money committed at the start. For a wedding whose list will move for a year, that's close to ideal: you're holding space for a crowd that doesn't exist yet, and you're not fronting a large sum to do it. Names get attached later, as people commit.

Holding rooms generally means a deposit for each guest from the start. That's a real amount of money committed before half your 'maybe' column has decided, and it's usually the organizer who's out of pocket while everyone makes up their mind. It can be workable, but it asks for more certainty earlier than a cruise does.

If a straggler has already booked their own cabin, it can usually be moved into the group and pick up the group's terms with it. That makes a late addition fairly painless, as long as there's still room on the ship.

Adding a guest is possible, but it needs room both on the plane and at the resort, and it's priced at the group rate on the day they join rather than the rate you first agreed. The window narrows as the trip gets closer, so waiting until the last minute is where it gets hard.

If your group holds more room than it fills, the space you don't use can be taken back. You're not stuck paying for cabins nobody sleeps in, but you also can't sit on empty room forever hoping it fills.

If the group ends up smaller than the size it was priced at, the whole booking can be re-priced, and some of what was included can fall away. A group that shrinks once has less give the next time. This is the surprise that catches organizers most often, so ask how far the group can drop before the price moves.

A big table for the whole group is a normal request on a ship, and the dining room is built to seat groups. You can usually eat together most nights without much fuss.

The buffet always seats everyone, at whatever times people wander in. The better restaurants, though, are usually bookable and often cap how many they'll seat at once, so a big group at one table is something to arrange ahead rather than assume. Ask how large a party each restaurant will take before you count on it.

A ship is a lot of different places at once. The teenagers, the grandparents, and the couple who want to be left alone can each have their own day and still meet for dinner. A larger group tends to be easier here, not harder, because a ship absorbs a crowd more comfortably than one resort can.

A resort spreads people out too, between the pools, the beach, and the bar, and everyone drifts back for meals. The catch is that a large group can strain a single resort, especially when it comes to rooms near one another. If keeping the group close together matters, ask early whether the resort can seat a party your size.

One week can hold a toddler and a grandparent, with activities running for each at the same time. Getting around is mostly step-free, though a big ship means walking, so a cabin near the lifts is worth asking for if someone in the group tires easily. Some ships run genuinely full programs for children; others less so.

A good resort does the same, with a kids' club, quiet corners, and short distances. But some clubs are more supervision than activity, and how much walking a day contains depends on how the place is laid out. Ask what the club does each day, and how far the rooms sit from the pool and the dining room.

The fare covers the cabin, the meals in the main rooms, and getting from place to place. A lot of the rest, the drinks, the shore trips, the specialty restaurants, gets spent once you're aboard, in US dollars. That's easy to underestimate when everyone's relaxed, so it's worth telling guests what's extra before they go.

More of the total is settled before you leave, in Canadian dollars, which makes it easier to tell a guest what the week will cost them. Two details move the number in ways organizers miss. It's counted by room, not by head, so a group of couples and a group of families in threes and fours are not the same booking. And how the rooms fill changes what the group earns and which deadlines bite.