A long but simple rail day with only two changes. Everything after arrival is optional except dinner.

1. 06:30
   Arrive at Sanremo station. It is underground and reached through a long tunnel walkway, so allow 15 minutes inside the station.
2. 06:53
   Intercity 505 Sanremo to Pisa Centrale, arriving 11:11 (4 h 18 min, no change). Reserve seats together; this train runs Monday to Friday.
3. 11:15
   At Pisa Centrale take the next regional train to Empoli (roughly every 30 minutes, about 40 to 50 minutes). Times from here on are approximate.
4. 12:15
   At Empoli change to the regional train for Siena (about 1 hour). Buy Pisa Centrale to Siena as one regional ticket.
5. 13:30
   Arrive Siena (between about 13:30 and 14:15 depending on the connection). Taxi from the station rank to the Airbnb, about 10 minutes.
6. 14:30
   Late bite instead of lunch: a cinta senese or finocchiona panino at Antica Pizzicheria de’ Miccoli on Via di Città. Then rest.
7. 18:00
   Slow first walk down to Piazza del Campo. Aperitivo at Le Tre Rane (small wine bar, Via di Stalloreggi 22) or a Campari at a café on the Campo itself for the view.
8. 20:00
   Dinner at La Taverna di San Giuseppe.

No vehicles today. The Duomo complex in the morning, a long lunch, an empty afternoon, and a hands-on Tuscan cooking class that becomes dinner.

1. 09:30
   Coffee and a pastry at Pasticceria Nannini on Banchi di Sopra, or at Pasticceria Bini on Via Stalloreggi for panforte and ricciarelli to take home.
2. 10:15
   Duomo complex with the OPA SI Pass: cathedral, Piccolomini Library frescoes, Museo dell’Opera and the climb onto the Facciatone. Allow about 2 hours. The pass is valid three days, so anything you skip can wait. The inlaid marble floor is mostly covered in April; it is fully uncovered in summer and autumn.
3. 12:45
   Lunch at Antica Trattoria Papei.
4. 14:30
   Back to the Airbnb. Nothing scheduled until the class.
5. 16:30
   Cooking class at Scuola di Cucina di Lella, Siena’s first cooking school (founded 1996), Via Fontebranda 69. About 4 hours, five recipes including hand-rolled pici, then you eat what you made with wine. Class times vary by season; book the evening session if one is offered on the 9th. If only a morning class runs, swap it with the Duomo block.
6. 21:00
   Nightcap at Charlie Mixology Bar, where Siena’s locals drink cocktails; the owner Riccardo is known for house-made canned cocktails.

A full day in a small van, maximum eight guests, with three Brunello producers, lunch at a winemaker’s family table, the town of Montalcino and the abbey of Sant’Antimo. You do nothing but taste and look.

1. 09:15
   Walk to Piazza San Domenico. Meet the guide at the steps of the red-brick basilica.
2. 09:30
   Tuscan Escapes, small-group Brunello di Montalcino trip departs. The drive south runs about 1 h 30 min through the Crete Senesi clay hills. The order of stops below follows the operator’s description; the clock times after departure are estimates.
3. 11:00
   First winery: a small producer, a walk in the vines, the cellars, and a Rosso and Brunello tasting.
4. 12:30
   Free time in Montalcino: the fortress, the views, an espresso.
5. 13:30
   Lunch at a family winery with the owners (recent guests report Cava d’Onice and Bellaria): Tuscan antipasti, house pasta, dessert with vin santo, their wines throughout.
6. 15:30
   Abbey of Sant’Antimo, a Romanesque church in an olive valley; the monks sometimes sing Gregorian chant during the visit.
7. 16:30
   Third winery and final tasting. Most wineries can ship cases home; ask at each stop.
8. 18:30
   Back at Piazza San Domenico (the tour lasts about 9 hours). Walk 5 to 10 minutes to the Airbnb.
9. 20:00
   Light dinner at Osteria Il Grattacielo, or skip dinner entirely after a winery lunch.

The same operator, a shorter day and a different wine: Castello di Brolio, where the Chianti formula was written down in the 1800s, then lunch and a cellar tour at a small family estate.

1. 09:15
   Walk to Piazza San Domenico, same steps as yesterday. Confirm the exact departure time on your booking.
2. 09:30
   Tuscan Escapes, small-group Chianti trip with wine tasting departs: the gardens and ramparts of Castello di Brolio and a tasting of its Chianti Classico. Clock times after departure are estimates.
3. 13:00
   Lunch at a small Chianti wine estate with the producer (recent guests mention Casanova di Bricciano), then a cellar visit.
4. 17:30
   Back at Piazza San Domenico (about 8 hours). Rest.
5. 20:00
   Dinner at Osteria Il Carroccio.

A slow morning and a two-hour train through the Crete Senesi and the Val di Chiana, with a picnic from Siena’s best salumeria.

1. 09:30
   Last Siena breakfast. Optional: climb the Torre del Mangia (about 400 steps) if your legs want it, or simply sit on the Campo.
2. 11:00
   Check out (ask the host for luggage space until 12:45 if checkout is earlier). Buy the train picnic at Antica Pizzicheria de’ Miccoli: cinta senese prosciutto, finocchiona, pecorino, bread, and a bottle.
3. 12:45
   Taxi to the station (book it the night before: Radio Taxi +39 0577 49222).
4. 13:25
   Regional train Siena to Chiusi-Chianciano Terme, about 1 h 25 min, through Asciano and the Crete Senesi.
5. 14:50
   Arrive Chiusi-Chianciano Terme and change to the regional train towards Roma, which leaves about 10 minutes later. Check the departure board for the platform.
6. 15:26
   Arrive Orvieto. The 2026 timetable gives 13:25 to 15:26 (2 h 01 min). Take the funicular to Piazza Cahen, then the A bus or a 10 to 15 minute flat walk along Corso Cavour.
7. 18:00
   Aperitivo at Cantina Foresi, facing the Duomo façade.
8. 20:00
   Dinner at Trattoria del Moro Aronne.

A private guide and driver, two Orvieto Classico estates in the hills around the rock, eight wines and a light lunch, and back in town by mid-afternoon.

1. 09:30
   Slow breakfast at Bar Montanucci on Corso Cavour, a century-old pastry shop and chocolate maker.
2. 11:00
   Orvietoviva / Teseotur, Orvieto Classico Guided Tour: private wine-expert guide and driver, collected in Orvieto centre. Two wineries, eight wines with local snacks and a light lunch. Typical estates around Orvieto include Palazzone, Decugnano dei Barbi, Tenuta Le Velette and Custodi, several with ageing caves dug into the tufa.
3. 15:00
   Dropped back in the centre (about 4 hours). Rest.
4. 18:00
   Sunset walk through the medieval quarter to the church of San Giovenale at the western tip of the rock.
5. 20:00
   Dinner at Trattoria La Palomba.

Across the border into the Tuscia: the cliff village of Civita di Bagnoregio in the morning, freshwater-fish lunch on Lake Bolsena, and a family wine cellar under Montefiascone in the afternoon. A private driver handles every leg and brings you back to Orvieto.

1. 09:30
   Driver collects you in Orvieto centre.
2. 10:00
   Civita di Bagnoregio (about 25 minutes). Buy the access ticket at the belvedere (about €5 on 2026 reports), then walk the 300 m footbridge. The last stretch to the gate is steep; go slowly. About 1 h 30 min in the village.
3. 11:45
   Drive to Bolsena (about 25 minutes). Stroll the lakefront.
4. 12:45
   Lunch at Trattoria da Picchietto.
5. 14:45
   Drive to Montefiascone (about 20 minutes). Walk up to the Rocca dei Papi for the view over the whole lake.
6. 15:30
   Antica Cantina Leonardi: family cellar tour in the caves under the town, tasting of at least three wines including Est! Est!! Est!!! di Montefiascone, with bread, oil, cheese and ham. About 1 h 30 min.
7. 17:00
   Drive back to Orvieto (about 35 to 40 minutes), arriving around 17:45.
8. 20:00
   Light evening: a tagliere and a glass at Bottega Vera or Cantina Foresi, or dinner at Trattoria dell’Orso if it is open.

Orvieto’s two essentials in the morning, a last Umbrian lunch, and the 15:27 train to Roma Termini.

1. 09:30
   Duomo di Orvieto and the Cappella di San Brizio with Luca Signorelli’s Last Judgement frescoes. About 1 hour.
2. 11:00
   Orvieto Underground guided tour (about 1 hour) through Etruscan and medieval caves, wells and pigeon dovecotes under the city; tours leave from the office on Piazza del Duomo. Skip it if you would rather sit in the piazza.
3. 12:30
   Lunch at Trattoria La Grotta.
4. 14:30
   Collect bags. A shuttle or taxi to Piazza Cahen, then the funicular down to the station.
5. 15:27
   Regional Veloce Orvieto to Roma Termini, about 1 h 15 min to 1 h 25 min on the 2026 timetable. Next fallback: 17:29.