Where did you go on holiday this summer?
'Vacanza' = va-CAN-za, stress on second syllable. 'Quest'estate' = que-STE-sta-te.
Ask this at a late summer or autumn party as a warm and universally interesting conversation topic. Italian holidays are richly stories-worthy — people return with food discoveries, cultural experiences, and adventures to share.
'Essere stati in vacanza' (to have been on holiday) uses 'essere' as auxiliary for 'stare' (to be/stay in a place). 'Quest'estate' is a contracted form of 'questa estate' — the vowel at the start of 'estate' causes the contraction.
Hai fatto un bel viaggio quest'anno?
Did you have a good trip this year?
More general — not limited to summer
Sei rimasto/a in Italia o sei andato/a all'estero?
Did you stay in Italy or go abroad?
Interesting binary — Italians often holiday beautifully within Italy
Dov'è che hai consigliato di andare l'anno prossimo?
Where would you recommend going next year?
Asking for travel recommendations based on their experience
Puglia (Apulia) has become one of Italy's most fashionable holiday destinations in recent years, often described as the new Tuscany. Lecce is known as the 'Florence of the South' for its extraordinary baroque architecture. Italian holiday conversations are detailed and enthusiastic — expect restaurant names, beach recommendations, and food discoveries.