The brief: six people — a mix of close friends and family — gathered in Italy for a 60th birthday. Three days inside Florence, three days at Castello di Brolio in the Chianti. Two different Tuscanies in one trip, with time built into both halves to simply be there.
Day 1 — Arrive Florence
Flights into FLR, the small airport that puts you in the city in fifteen minutes. Check-in at San Firenze Suites & Spa — a converted palazzo steps from the Piazza della Signoria. First afternoon is unscheduled. The neighborhood rewards wandering: the Piazza della Repubblica for a coffee, the covered market, the quiet streets behind the Uffizi. First dinner is close to the hotel. The idea on Day 1 is to arrive, not to perform.
Day 2 — The Uffizi, the Piazza, the Duomo
Early-entry tickets at the Uffizi — the Botticellis and the Caravaggios before the school groups. Lunch at a table on the Piazza della Repubblica. Afternoon in the Duomo quarter: the baptistery doors, the narrow streets behind the cathedral, the climb up Brunelleschi's dome for the group willing to do it. Evening aperitivo on the Piazza della Signoria, which never gets ordinary. Dinner reservation in the neighborhood.
Day 3 — The Accademia, Boboli, Piazzale Michelangelo
Morning at the Accademia — the David, and the four unfinished Slaves that most visitors walk past too quickly. Boboli Gardens after lunch: shaded gravel paths, the amphitheater, a long slow afternoon. Piazzale Michelangelo at six — the view across the rooftops as the light shifts from gold to gray is the one photograph everyone takes and none of them adequately captures. Dinner in the neighborhood, an early night before the transfer south.
Day 4 — Transfer to Castello di Brolio · The birthday
Morning checkout. Private van south through the Chianti — an hour through vineyards and olive groves. Castello di Brolio is a ninth-century estate above Gaiole in Chianti, still owned by the Ricasoli family, who established the Chianti Classico formula here in the 1870s. The birthday celebration was arranged here: a private wine tasting hosted by the estate's winemakers, working through the Barone Ricasoli portfolio with the people who made it. Lunch afterward at Osteria di Brolio — the estate's own restaurant — with a custom cake the chef had prepared for the occasion. Afternoon at leisure: the castle walls, the chapel, the long view over the vineyard. No other plans required.
Day 5 — Siena
Forty minutes south. A guide meets the group at the city gate and leads them in on foot — the Campo, the Duomo, the Palazzo Pubblico. Lunch with a view of the Campo, the afternoon at the group's pace. Back to Brolio before dark. Dinner at the villa.
Day 6 — Radda in Chianti & Ristoro di Lamole
Morning in Radda in Chianti — one of the medieval hill towns at the center of the Classico zone. Small enough to see in two hours, good enough to want more. Lunch at Ristoro di Lamole in the village of Lamole above Greve: a short seasonal menu, a terrace with a long view across the valley. Afternoon back at the estate. Departures the following morning to FLR.
This trip was built around one birthday. Yours would be built around something different — or nothing in particular, which is its own kind of reason to go.
