Slow trip
10 slow days of art and history: Montalcino and Porto San Giorgio
10 days based in Montalcino and Porto San Giorgio, in October, built around art and history. Montalcino gets 4 days, with San Casciano dei Bagni, Castelnuovo Berardenga and Montepulciano nearby. Porto San Giorgio gets 6 days, with Senigallia, Ripatransone and Grottammare nearby.
10 days · October · art & history-first · moderate walking
Montalcino
Montalcino, 4 days
Base yourself in Montalcino and make these your day trips.
4 towns · qualifying pool of 8 from 83 candidates
Hill towns in the province of Siena. Brunello di Montalcino DOCG, Chianti Classico DOCG, TCI Bandiera Arancione, and wine territory.
Getting around
Rent a car for this corner. Only 1 of the 4 towns has a railway station; the day trips assume driving.
Your timing
October sits in this corner's best window: open, temperate, and short of the crowd months.
While you're there
- Montalcino · Sagra del Tordo, OctoberLast weekend of October medieval festival since 1958 with archery contest between the four quarters, Brunello tastings and historic procession.
Day 1 · Arrive in Montalcino
Settle in. Montalcino is your base for the next 4 days. Take the afternoon to walk the centro, find your bearings, eat something local.
Day 2 · Day trip to Montepulciano
First outing. Head to Montepulciano for the day. Take the slow road, leave time to wander, be back in Montalcino for dinner.
Day 3 · Day trip to Castelnuovo Berardenga
Out again, this time to Castelnuovo Berardenga. Same rhythm: leave after breakfast, return for evening in Montalcino.
Day 4 · Day trip to San Casciano dei Bagni
Last day trip in this corner, to San Casciano dei Bagni. Make a day of it, then back to Montalcino.
Porto San Giorgio
Porto San Giorgio, 6 days
Base yourself in Porto San Giorgio and make these your day trips.
4 towns · qualifying pool of 10 from 125 candidates
Coastal and hill towns across 4 provinces, among them Fermo, Ascoli Piceno, and Ancona. Borghi Più Belli d'Italia, Bandiera Blu coast, and Spighe Verdi.
Getting around
Porto San Giorgio, your base, is on the rail network. 2 of the 4 towns here have a station; the rest need wheels. A rental car makes this corner simple, a rail-plus-taxi version takes patience.
Your timing
October sits in this corner's best window: open, temperate, and short of the crowd months.
Day 1 · Arrive in Porto San Giorgio
Settle in. Porto San Giorgio is your base for the next 6 days. Take the afternoon to walk the centro, find your bearings, eat something local.
Day 2 · Day trip to Grottammare
First outing. Head to Grottammare for the day. Take the slow road, leave time to wander, be back in Porto San Giorgio for dinner.
Day 3 · Day trip to Ripatransone
Out again, this time to Ripatransone. Same rhythm: leave after breakfast, return for evening in Porto San Giorgio.
Day 4 · Day trip to Treia
Out again, this time to Treia. Same rhythm: leave after breakfast, return for evening in Porto San Giorgio.
Day 5 · Day trip to Senigallia
Last day trip in this corner, to Senigallia. Make a day of it, then back to Porto San Giorgio.
Day 6 · Day in Porto San Giorgio
A slower day. Stay in Porto San Giorgio. Walk side streets, find the market, take a long lunch.
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About this plan
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