Suggested Day Trip Itineraries

A quick note from Dave & Mike: these aren't marching orders. Our goal is simply to do a little legwork before we leave so that once we're there, we can put the phones away, wander, eat well, and just live it. Italy rewards the unhurried — and that's exactly what we're after.

That said, a little structure goes a long way in a foreign country. Knowing where to park, which restaurant to book, and roughly how the day flows means fewer decisions on the ground and more time just enjoying the moment. Think of these as a head start, not a schedule.

If any of these sound like your kind of day, let us know in the group text — we'll do our best to get it on the calendar. And if you have ideas, restaurant suggestions, or a place we should know about, send those along too. The more input the better.

Each itinerary below covers routes, timing, parking, restaurant picks, and logistics — all in one place. More will be added as we finalize the calendar.

View Excursion Priority Matrix →
Puglia Day Trips from Ostuni
One per week is plenty
🗺 Day Trips from Ostuni
Alberobello
35 min
The trulli capital of the world — conical stone houses that look like they grew from the earth. Go early before the coaches arrive. Pair with nearby Locorotondo and Martina Franca for the perfect Valle d'Itria loop.
Polignano a Mare
40 min
Dramatic clifftop old town perched over a turquoise Adriatic cove. The beach at Lama Monachile — wedged between limestone cliffs — is iconic. Gelato mandatory. Best in the morning before day-trippers arrive from Bari.
Lecce
1 hr
Puglia's baroque capital. The honey-coloured stone of the cathedral, Santa Croce basilica, and the Roman amphitheatre is stunning. Easy to walk. Good for a full day with lunch and shopping in the old town.
Matera
1.5 hrs (1–2 nights)
Technically Basilicata, not Puglia, but unmissable. The UNESCO-listed sassi (cave dwellings) cut into the gorge are unlike anything in Europe. Plan at least one overnight — the town after the day-trippers leave is extraordinary. Book ahead; Matera has excellent small hotels in renovated cave houses — expect approximately $250/night.
Tuscany Day Trips from Pergine Valdarno
All under one hour's drive
🗺 Day Trips from Pergine Valdarno
Cortona
35 min
Medieval hill town with extraordinary views over Lake Trasimeno and the Valdichiana. The Museo dell'Accademia Etrusca has one of the finest Etruscan collections in Italy. Walk the ramparts in the late afternoon — the light is remarkable.
Sansepolcro
40 min
Birthplace of Piero della Francesca. The Museo Civico contains his Resurrection fresco — Aldous Huxley called it the greatest painting in the world. Completely unrushed, very local. Combine with a drive through the upper Tiber valley.
Anghiari
40 min
Perfectly preserved medieval village on a hill above the Tiber plain. Famous for the Battle of Anghiari (and Leonardo's lost painting). Beautiful streets, local weaving tradition, and a handful of honest restaurants.
Casentino Valley
45 min north
Drive north through Poppi — whose castle dominates the valley — then into the Casentino National Forest, one of the most unspoiled forest landscapes in Italy. Continue to the Camaldoli monastery (11th century hermitage) or the Sanctuary of La Verna. A full, deeply peaceful day.
Montepulciano
55 min
Renaissance hilltop wine town. The main piazza is one of Tuscany's finest. Go down into the medieval cellars to taste Vino Nobile di Montepulciano — one of Italy's great reds. Cantine Gattavecchi is the standout: a 16th-century cellar carved directly beneath the church of Santa Maria dei Servi, producing excellent Vino Nobile and Rosso di Montepulciano. They offer cellar tours and tastings, and their terrace restaurant serves Tuscan lunch with views over the Val di Chiana — reserve ahead.
San Gimignano
75 min
The medieval "City of Beautiful Towers" — 14 surviving towers still dominate the skyline as they have since the 13th century. Go early before the tour buses arrive; by mid-morning the main street fills quickly. The Vernaccia di San Gimignano (Italy's first DOC white wine) is excellent and best tasted at a local cantina rather than a tourist shop. The Museo Civico in the Palazzo del Popolo has fine Sienese and Florentine paintings. Combine with a drive through the surrounding vineyards on the way back.
Siena
60 min
The Campo and the Duomo are always worth a return. In June, the city is alive with preparations for the Palio (July 2). Early morning visit to the Duomo before crowds arrive.
Special Overnight
🏰 Castello di Verrazzano
Albergo Casa Al Sole · Greve in Chianti · Overnight Jun 6–7 · ~70 km from villa

Castello di Verrazzano →

A working Chianti wine estate centred on a 16th century castle that belonged to the family of Giovanni da Verrazzano, the Florentine explorer who discovered New York Harbor in 1524. The estate produces outstanding Chianti Classico and extra-virgin olive oil. This is the right kind of Chianti experience — authentic, unhurried, and deeply rooted in the land. Plan 1–2 nights.

Rooms
~$150/night for a double room. Recently restored with vineyard views.
Winery
Wine tasting dinner ~$80/person — a guided evening through the estate's Chianti Classico, Vin Santo, and olive oil, ending at the table. Daily tours & tastings also available.
Nearby
Greve in Chianti (5 km) — the charming market town at the heart of Chianti Classico country. Also: Panzano (Dario Cecchini's legendary butcher) and Radda in Chianti.
Getting There
~1 hr 15 min via SR 69. Scenic approach through Chianti hills from Figline Valdarno.
Status
✓ Hotel confirmed · ✓ Cena in Fattoria booked · Jun 6–7 · Dave · Mike · Jane · Chuck