One Villa, Three Generations: The Booking Checks That Save the Holiday

There's a particular kind of Italian villa photo that gets shared in the family WhatsApp group at 10pm: long table under a pergola, cypress trees, a pool catching the last of the light. Everyone replies with heart emojis. Nobody replies with the question that actually decides whether the week works — where does Grandma sleep, and how many steps are between her bed and the loo at 3am?

Multigenerational trips are wonderful and they are also a small engineering project. Get the house right and three generations rub along beautifully. Get it wrong and you spend seven days managing other people's discomfort. Here's what to look at before you pay a deposit for summer 2026.

Start with the floor plan, not the gallery

Ask the owner for a proper floor plan with levels marked. In Italy, "ground floor" can mean anything from street level to four steps up from a gravel track, and "first floor" is what we'd call the first floor — one flight up. If anyone in the party is unsteady on their feet, you want a bedroom and a bathroom on the same level as the entrance, with no exterior stairs to negotiate after a glass of wine.

Request photos of the actual entrance route: the gate, the path, the door threshold, any internal steps. Owners who have hosted older guests will usually have these to hand. Owners who haven't may send you a shot of the view instead, which tells you something.

Handrails are rarer than you'd think. So are grab rails in bathrooms. If they matter, say so early and ask for specifics rather than a vague "it's fine for older people".

The bathroom arithmetic nobody does

Rule of thumb: one bathroom per three people, minimum, and at least one of them on the grandparents' floor. Six people sharing a single bathroom is fine in a tent. In a villa in August, with everyone wanting to be out by half nine, it's a daily negotiation.

While you're there, ask three questions that owners rarely volunteer answers to:

• Is the shower a walk-in, or a shower over a bath? (The Italian for bath is vasca — worth recognising in listings.)
• Is there a separate WC, and is it upstairs?
• How is the hot water — tank or on-demand, and does it cope with six showers in a row?

Shade is a facility, not a nicety

A west-facing terrace is glorious in April and punishing in July. Look for a covered area — pergola, loggia, deep eaves, mature trees — where someone can sit at 3pm with a book and not wilt. Ask whether there are umbrellas and how many, and whether there's a genuinely cool indoor room for the hottest part of the day. Thick stone walls do a lot of work; air conditioning in bedrooms helps at night, though some grandparents will refuse to switch it on. Ceiling fans and mosquito screens are the quiet heroes of a good night's sleep.

Seating matters more than it sounds. Six chairs at the outdoor table is not the same as somewhere soft to sit with a bad back. Ask.

The pool, described honestly

This is where listings get vague. You want depth at both ends, not "1.2m–2m" as a single figure. You want to know whether entry is by ladder, by roman steps, or by a shallow shelf — the last is much easier for anyone with a hip replacement. You want to know whether the pool is fenced or gated, whether there's an alarm or cover, and whether it's shared with another property. Fencing is uncommon in rural Italy, so supervision does the work; just don't book believing a barrier exists when it doesn't.

If you're travelling in May, late September or October, ask about heating. An unheated pool in Tuscan October is a bracing experience for adults and a non-starter for small children.

The walk to the village, measured properly

"400 metres to the village" can mean a flat pavement stroll or a steep, unlit lane with no verge and a blind bend. Grandparents may want a morning coffee run; parents may want to walk to dinner with a pushchair. Ask the owner for a photo of the route from the gate to the piazza, and ask specifically whether the last stretch is tarmac or white gravel track. Ask about taxis, too — useful for the return leg after a long lunch.

The list to send before you book

• Floor plan with levels and steps
• Bed configuration, including whether twins can be made into doubles
• Bathroom count per floor, with shower types
• Pool depths, entry type, fencing and heating
• Air conditioning in which rooms, and mosquito screens
• Cot, highchair and stair gate availability (and whether they're extra)
• Distance and terrain to the nearest shop, bar and restaurant
• Whether the owner lives on site or nearby, and how reachable they are

A short video call walk-through is worth more than fifty photos. Ask, too, whether they've hosted grandparents before and what those guests found tricky. Owners who've done it will tell you straight.

When two places beat one

Sometimes the kindest answer is not a bigger villa. A main house for the family plus an annexe or a small hotel five minutes away gives grandparents quiet mornings and an early night, and gives parents the late-evening kitchen table without worrying about the noise. It can cost less than you'd expect — a village B&B room for two is often cheaper than the step up to a five-bedroom villa with a second bathroom.

Be honest with yourself about the group, not the brochure. If your parents would rather have their own front door, book them one. Everyone will be better company at dinner.

The boring bits that protect the trip

Book something with a clear cancellation policy, and read it properly. Sort travel insurance early, declaring any pre-existing conditions — premiums rise with age and with every undeclared detail. Carry the GHIC card, keep medication in hand luggage, and check before you fly whether the villa fridge has space for anything that needs to stay cold.

None of this is the glamorous part of planning. It's the part that means the pergola photo, when it finally happens, is a picture of six people genuinely relaxed rather than one person quietly working out how to get up the stairs.