Multigenerational Villa Holiday in Puglia: A Masseria for Three Generations
A holiday with three generations is the most beautiful and the hardest to organise. Grandparents want shade, quiet and meals at set times; parents want to switch off; teenagers want the sea, wifi and freedom; children want somewhere to run. Putting everyone in a single villa means forced cohabitation; splitting them across different hotels means not really being together. The format that works exists, and it is that of the Salento masseria: independent units around a shared courtyard.
Together, each at their own pace
At Masseria Montanari the family spreads out across 6 independent units, two rooms, two apartments and two studios, for 14 permanent sleeping places and up to 16 with the extra ones. Each household has its own door, its own bathroom, its own kitchen and its own hours: the grandparents dine early and retire, the teenagers stay up late in the garden without waking anyone, the baby has a quiet room. The whole masseria page has the exact table of who sleeps where, to share in the family group chat before you even book.
The centre of gravity: the long table and the garden
The beauty of a multigenerational holiday is the moment everyone comes together. Here it has two places: the vaulted stone hall for the dinner with everyone, climate-controlled, cool in August and warm at Christmas, and the garden where the children run while the grown-ups stay at the table. The wood-fired oven and the barbecue are the excuse for the evening when the grandparents cook and the grandchildren learn. And every unit has its own kitchen: breakfast each in their own way, a quick pasta at six for the little ones.
A programme for every age
Salento lends itself well because distances are short and the options many:
- For the children: the shallow, sandy beaches on both coasts, twenty or thirty minutes away; the Alimini lakes with their calm water.
- For the grandparents: the villages of the Grecìa Salentina five minutes away, with a stroll in the piazza and a pasticciotto at the café; Otranto and Lecce at an unhurried pace, at the right hours.
- For the teenagers: the sea at Torre Sant'Andrea for snorkelling, the summer festivals and the pizzica, evenings in the garden with family friends.
- For everyone: the slow day at the masseria, the one when nobody goes anywhere and the photo album comes out.
The maths, with three generations
The whole masseria for exclusive use goes from 500 to 800 euros per day depending on the season. Divided among 14 or 16 people, the cost per person drops below that of many scattered hotel rooms, and the kitchen cuts the restaurant bill: with three generations, eating out every evening is the expense that blows the budget. And a single figure to split also settles the "who pays for what".
When to come
May, June and September are the golden months: perfect climate for the grandparents, sea already warm for the children, better prices. July and August for those who want full summer and the festivals. The Christmas and New Year holidays are when scattered families come together, and the masseria is open all year round: the New Year's Eve party at the masseria has its own guide. For those arriving from far away: Brindisi airport is an hour away, Bari two.
The first step
Write to us with your dates, how many you are and the ages: we reply within a few hours with the recommended arrangement of the units and a clear quote, to pass around the family. Those coming from far away to reunite will also find the family reunion guide here: the masseria has been hosting whole families for three hundred years. Yours is next.

