Hawaii
The islands hold a large family better than almost anywhere. The flight is long enough that people stay a week rather than a weekend, and once everyone’s there, nobody’s in a hurry.
It’s also where our name comes from, so we take it personally.
Which island
This is the first real decision, and for a group it matters more than the property. The islands are genuinely different, and the right one depends on who’s coming.
Maui
The most familiar, and the easiest sell to a group where not everyone has been. Good beaches, enough restaurants to absorb twenty people, and resorts built for families. If half your group wants to do nothing and half wants an agenda, Maui handles both.
Kauai
Quieter, greener, more dramatic. Fewer places to eat and further between them, which is either the appeal or the problem depending on your group. Best for families who want to be together rather than dispersed, and for anyone who’d rather hike than shop.
The Big Island
The one where there’s something to see. Volcanoes, black sand, snow on the mountain and sun on the coast in the same afternoon. Long drives, so it suits groups who want to do things rather than settle into one beach. Also the best golf.
Oahu
Underrated for groups and usually the best value. Easiest to fly into, most rooms, most restaurants, and enough history and city to fill the days people don’t want to spend on a beach. Worth considering when the budget spread across a family is wide.
What changes when there are twenty of you
Resort or houses
The fork that decides the whole week. A resort gives you service, pools, restaurants and separate rooms with separate bills. A house or two gives you one kitchen, one living room and everyone under one roof. Families who choose a house because it’s cheaper sometimes discover they’ve signed up to cook for twenty. Families who choose a resort sometimes never see each other.
There’s a middle option most people don’t know about: adjacent units at a resort, or a resort with residential-style villas. Kitchen and living space, with a front desk.
Where the rooms are
Hawaiian resorts are large. Nine rooms booked separately can end up in three towers a ten-minute walk apart, which quietly ruins the point of everyone being there. Booked together and asked for properly, they don’t.
Dinner for twenty-two
Good restaurants in Hawaii book out, and large tables book out further. The one night everyone eats together has to be reserved months ahead. A luau is often the easy answer for that night — it absorbs a big group comfortably and the kids are entertained.
Arriving from everywhere
A family flying in from four cities lands across a twelve-hour window, and the last arrival is often after midnight local time. Transfers, keys and someone awake at the desk all need arranging, or the first day is spent recovering rather than starting.
Cars, and how many
Most groups need fewer than they think and book more than they need, then pay resort parking on all of them. Worth deciding deliberately rather than everyone renting their own.
When to go, and when to book
Hawaii is pleasant year-round, so timing is about crowds and cost rather than weather. Christmas, spring break and midsummer are the expensive weeks and the ones that sell out first. Late spring and September are the sweet spots — quieter, cheaper, and the water is still warm.
For a group of any size, start nine to fifteen months out. Not because it can’t be done later, but because the rooms that let a family stay together go first, and the alternative is a compromise you’ll feel all week.
Going as a guest
Hawaii is a place people live, not a resort with an ocean attached. The islands have asked visitors to travel more thoughtfully — to spend in local businesses, to stay on the trails, to keep a distance from the turtles and the monk seals, and to treat the places that are sacred as sacred.
We’ll point your group toward the operators and restaurants that are actually of the place, and away from the things that aren’t. It makes for a better week anyway.
Tell us who’s coming.
We’ll tell you which island fits your group before we talk about a single hotel.
ʻOhana Getaways 