Last summer we did a Tuscany road trip that mixed classic towns, wineries, and slow countryside days — without bouncing hotels every night. This itinerary is written as 9 days total (Rome on the front and back end), but I included a true 7-day Tuscany-only version at the bottom if you’re short on time.
At a glance (where we based ourselves)
- Night 1: Orvieto (easy first stop after landing in Rome)
- Nights 2–5: Montalcino / Val d’Orcia area (Castello Banfi) Curated Compass Journeys
- Nights 6–7: Cortona Curated Compass Journeys
- Night 8: Rome Curated Compass Journeys
This itinerary is best for: wine + food, pretty drives, small towns, and a calmer pace.
Not ideal for: people who want to “see everything” in a week (Florence/Pisa/Cinque Terre every day, etc.).
Day 1: Land in Rome → drive to Orvieto
Arrive in Rome, pick up your rental car, and drive to Orvieto. Check into B&B La Magnolia, then spend the afternoon exploring the historic center — Orvieto Cathedral, St. Patrick’s Well, and Museo Claudio Faina. If you’re up for it, climb Torre del Moro for the views. Dinner at I Sette Consoli.
Day 2: Orvieto → Val d’Orcia base (Castello Banfi)
Keep the morning in Orvieto and do the Orvieto Underground tour (this one’s worth booking ahead). Grab lunch at Trattoria la Grotta, then drive into Tuscany and check into Castello Banfi – Il Borgo. Settle in and do dinner at La Taverna on-property.
Day 3: Val d’Orcia towns day
Spend the day with Serena (A Day in Tuscany) exploring the classic Val d’Orcia towns — Pienza, Monticchiello, and Bagno Vignoni. Enjoy lunch in Pienza, then head back for a relaxed evening. Dinner at Trattoria Il Leccio in Sant’Angelo in Colle — my favorite restaurant in this area.
Day 4: Banfi tasting + Montalcino
Start with a wine tasting at Castello Banfi, then head into Montalcino to wander, shop, and take in the views. Dinner at La Taverna di Baietto (great mix of traditional + modern).
Day 5: Brunello day (tastings + abbey)
Scenic drive through Brunello wine country (Rick Steves-style route). Stop at Tornesi for a tasting + a Tagliere Toscano platter, then lunch at Trattoria II Pozzo in Sant’Angelo in Colle. In the afternoon, do a private tour + tasting at Ciacci Piccolomini D’Aragona, then stop by Sant’Antimo Abbey before heading back for dinner at La Sala dei Grappoli at Castello Banfi.
Day 6: Mastrojanni → Cortona
One more Brunello stop: Mastrojanni for a wine experience. Check out of Castello Banfi and drive to Cortona. Check into Monastero di Cortona Hotel & Spa, then dinner at Osteria Del Teatro.
Day 7: Cooking class + Cortona evening
Cooking class with Simonetta at Casa Bellavista (such a fun, memorable experience). Keep the afternoon flexible — explore Cortona or lean into the spa at the hotel. Dinner at La Loggetta for great food + views.
Day 8: Cortona → Rome
Drive back to Rome and check into Palazzo Navona Hotel. Spend the day hitting any landmarks you missed or just wandering neighborhoods at your own pace. Dinner at Roscioli Salumeria con Cucina.
Day 9: Depart Rome and Fly home
Important Notes
Reserve Orvieto Underground in advance.
In Tuscany, tastings often require reservations (especially the bigger names).
Don’t overbook your days — drives take longer than you think once you factor in photo stops and small town wandering.
Comments +