Tuscany & Umbria Road Trip

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Among the countless memorable travel experiences the world offers, a certain number of them can be classed as truly great. A Tuscan driving tour is one such experience. The region draws me back again and again. Roads thread a rolling countryside of vineyards, olive groves and pastures punctuated by cypress allées, ancient hill towns, stone farmhouses and the occasional castle. Although some of the byways are narrow, few are nerve-wracking or poorly maintained, and each bend seems to present a view that’s better than the last. A road trip here offers great variety — wine, food, history, art — and just as important, there are numerous well-serviced and character-rich places to stay.

On my most recent trip to Italy, I discovered four delightful new resorts and tested three previously recommended properties. No one would want to follow such an itinerary on a vacation, but my five favorite hotels of the trip could be strung together into a sensational two-week journey encompassing some of the best of Tuscany and Umbria. Of course, it would also be possible to have a wonderful time at just two or three of them, perhaps in combination with Florence. One of our Italy experts in the Travel Office can help you put together an itinerary that’s precisely right for you.

Read our editor’s full trip report to Italy.

Highlights:

  • Explore some of the world’s loveliest countryside 
  • Tour high-quality wineries in gorgeous settings
  • Visit picturesque hill towns such as Montalcino, Montepulciano and Monteriggioni
  • Overnight in glamorous castles and converted medieval villages
  • Dine in Michelin-starred restaurants and sip wine in charming enotecas
  • Take treatments in atmospheric spas beneath ancient stone vaults
  • Lounge beside striking pools with panoramic views of Tuscany

Day 1: Florence – Montalcino

Terrace of the UNESCO View Terrace Suite, Castello di Velona, Castelnuovo dell’Abate
Terrace of the UNESCO View Terrace Suite, Castello di Velona, Castelnuovo dell’Abate - Castello di Velona

Pick up a rental car at the Florence airport and drive about two hours south to the Castello di Velona, a converted castle crowning a hill with stupendous views of the Montalcino countryside. Ideally, book a UNESCO View accommodation overlooking a vast swath of the Val d’Orcia below.

After you check in, have a stroll through the vineyards, or relax by the pool or in the spa.

Have dinner tonight at Settimo Senso, the resort’s more casual Tuscan restaurant.

Overnight at the Castello di Velona.

Day 2: Montalcino

Bar terrace, Castello di Velona
Bar terrace, Castello di Velona - Photo by Andrew Harper editor

Take this morning to visit the hill town of Montalcino itself. It has an impressive castle at one end, and the friendly Da Rizieri enoteca has a large selection of Brunello di Montalcino bottlings to taste from its Enomatic machines. Have lunch on the panoramic terrace of Boccon Divino, just outside of the old center. Return to your hotel and enjoy a spa treatment. Body scrubs can be a most refreshing antidote to jet lag.

Have dinner at the hotel’s intimate gastronomic restaurant, Il Brunello.

Overnight at Castello di Velona.

Day 3: Montalcino

Main swimming pool, Castello di Velona
Main swimming pool, Castello di Velona - Photo by Andrew Harper editor

Today, I recommend doing a tour and tasting at a nearby winery, perhaps the excellent Podere le Ripi, which has a striking swirl-shaped cellar and biodynamically farmed vineyards (including perhaps the world’s only “bonsai vineyard”). The tasting can be paired with salumi and cheese.

Before returning to the hotel, visit the Romanesque Abbazia di Sant’Antimo, an abbey in an unusually picturesque setting not far from the Castello di Velona. 

Spend the rest of the afternoon relaxing beside the dramatic two-level swimming pool, filled with bathtub-warm thermal spring water.

For dinner this evening, perhaps take advantage of the Castello di Velona’s dine-around program and visit one of the off-property restaurants affiliated with the hotel.

Overnight at the Castello di Velona.

Day 4: Pienza – Montepulciano – Reschio

Castello di Reschio, Lisciano Niccone, Italy
Castello di Reschio, Lisciano Niccone, Italy - Philip Vile

Depart the Castello di Velona after one more breakfast on its terrace overlooking the Val d’Orcia. Drive northeast to Pienza, a gem of a town known for its main piazza, a masterpiece of Renaissance architecture. Have a stroll through the compact center and perhaps have a nibble of its famous pecorino cheese before continuing east to one of my favorite Tuscan hill towns, Montepulciano.

Have lunch at Il Pozzo, ideally on its patio overlooking a pretty little piazza, and perhaps do a tasting of Vino Nobile di Montepulciano at one of its enotecas. I recommend Borgo Divino (uphill) and La Bottega del Nobile (downhill).

Keep driving east, skirting the northern shore of Lake Trasimeno, and check into the glamorous Castello di Reschio, just over the border in Umbria.

After an aperitivo in the courtyard or the Palm Court Bar, have dinner in its gourmet Ristorante al Castello (request a table on the edge of its terrace when making your reservation).

Overnight at Castello di Reschio.

Days 5-6: Reschio

Swimming pool, Castello di Reschio
Swimming pool, Castello di Reschio - Photo by Andrew Harper editor

Spend two full days enjoying the formal but convivial atmosphere of the Castello di Reschio. The pool is exceptionally glamorous: a mirror reflecting mature umbrella pines and the 10th-century castle, with well-spaced loungers. The spa, in the castle’s former wine cellars, is incredibly atmospheric. I highly recommend a Watsu treatment in its “Roman bath,” a candlelit saltwater pool beneath a stone vault, or book a service in the couple’s treatment room, with side-by-side clawfoot tubs and a woodburning fireplace. The estate’s stables are also world-class — horseback riding here is a joy — and a hike with a naturalist guide is also great fun. The cooking classes are also excellent, and Castello di Reschio makes a good base for a day trip to Perugia and/or Assisi.

Have dinner one night in the more casual Ristorante alle Scuderie next to the stables, or perhaps twice. I loved our meal there, which was accompanied by a four-piece jazz combo.

Overnight at the Castello di Reschio.

Day 7: Reschio – Valdarno di Sopra

Avignonesi winery restaurant
Avignonesi winery restaurant - Photo by Andrew Harper Editor

Check out of the Castello di Reschio and drive northwest, back into Tuscany. Consider a lunch paired with wines at the acclaimed Montepulciano winery Avignonesi, and/or pause to explore the town of Cortona.

Continue up to Il Borro, a converted medieval village in the well-regarded Valdarno di Sopra wine region, a corner of Chianti. Perhaps do a tour and tasting in Il Borro’s cellars before dinner; the wines are served beneath a grand brick dome at well-spaced tables in the cellars.

Dine tonight in the hotel’s lively bistro, and then retire to your accommodations across the causeway in the tranquil medieval village.

Overnight at Il Borro.

Day 8: Valdarno di Sopra

Main infinity pool, Il Borro, San Giustino Valdarno
Main infinity pool, Il Borro, San Giustino Valdarno - Photo by Andrew Harper editor

You could certainly spend a full day relaxing at Il Borro, but I recommend booking a tasting and carriage ride through the vineyards at family-owned Tenuta Canto alla Moraia. The ride is a delight, and the wines are superb.

Alternatively, you could make a day trip into Arezzo, known for its high-end antiques and the Piero della Francesca frescos in the Capella Bacci (book tickets in advance).

Return to Il Borro. Relax by its main infinity pool, browse the handful of boutiques in the village, and/or visit the hotel’s unintentionally creepy Pinocchio museum. There’s also a full-service spa, a large stable, hiking paths and a three-hole golf course.

After an aperitivo at the bar, have dinner at the hotel’s gourmet restaurant, the Osteria del Borro.

Overnight at Il Borro.

Day 9: Valdarno di Sopra – San Felice

Bedroom of our Prestige Room, Borgo San Felice, Castelnuovo Berardenga
Bedroom of our Prestige Room, Borgo San Felice, Castelnuovo Berardenga - Photo by Andrew Harper editor

Check out of Il Borro and head today into the heart of the Chianti Classico region. We have long recommended the Borgo San Felice, which occupies another converted medieval village, but my recent visit confirmed that it ranks among the finest Tuscan resorts.

Check in, relax, and have dinner at its more casual restaurant, the Osteria del Grigio. Alternatively, the Michelin-starred family-owned L’Asinello is a short drive away.

Overnight at Borgo San Felice.

Day 10: San Felice

Borgo San Felice’s Michelin-starred restaurant, Poggio Rosso
Borgo San Felice’s Michelin-starred restaurant, Poggio Rosso - Tyson Sadlo

There are numerous fine ways to spend your day today. You might make the scenic drive up to Radda in Chianti to do a tasting and lunch at Casa Porciatti, and perhaps visit the sleek tasting room of the Vallepicciola winery before returning to Borgo San Felice.

But honestly, I might just remain on the property. Do a tour and wine tasting, perhaps the Pugnitello Rarities tour, which includes a visit to Borgo San Felice’s unique Vitiarium vineyard and a tasting of well-structured Pugnitello, an almost-extinct Tuscan grape variety. It’s also worth spending time in the hotel’s spa, with its airy relaxation lounge, hot and cold Kneipp pools, experience showers and pretty treatment rooms. And the well-serviced cypress-lined swimming pool is a very pleasant place to relax.

Dine tonight in Borgo San Felice’s Michelin-starred restaurant, Poggio Rosso.

Overnight at Borgo San Felice.

Day 11: San Felice – Casole d’Elsa

Ristorante Tosca terrace, Belmond Castello di Casole, Casole d’Elsa
Ristorante Tosca terrace, Belmond Castello di Casole, Casole d’Elsa - Photo by Andrew Harper editor

Drive southwest from Borgo San Felice, stopping perhaps for lunch at the welcoming Ristorante Albergaccio di Castellina. Alternatively or in addition, explore the hill town of Monteriggioni before checking into the Belmond Castello di Casole. This hilltop palace and adjacent village is one of Tuscany’s premier new resorts. 

Have an aperitivo on the panoramic terrace overlooking unspoiled countryside flanked by two ancient hill towns. Then have dinner in the hotel’s stylish Ristorante Tosca.

Overnight at Belmond Castello di Casole.

Day 12-13: Casole d’Elsa

Infinity pool overlooking the town of Casole d'Elsa
Infinity pool overlooking the town of Casole d'Elsa - Photo by Andrew Harper editor

Take two full days at the Belmond Castello di Casole. There are multiple possibilities for day trips: Volterra, Colle di Val d’Elsa, San Gimignano and Siena are all within an hour’s drive.

But I also highly recommend allowing ample time to enjoy the resort. Its infinity pool has a breathtaking view and is a wonderful place to while away an afternoon. The spa, once again in a former wine cellar, is both beautiful and highly professional. Hiking trails lace the vast property, and numerous other activities are available at the resort.

It’s a pleasure to eat at the hotel, but it’s also worthwhile to dine off the property at places like the Michelin two-star Arnolfo, in the old quarter of Colle di Val d’Elsa.

Overnight at Belmond Castello di Casole.

Day 14: Casole d’Elsa – Florence – Depart

Check out of the Belmond Castello di Casole, drive back to Florence and board your flight out of Italy.

Ready to book a trip?

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By Andrew Harper Editor Andrew Harper editors travel the world anonymously to give you the unvarnished truth about luxury hotels. Hotels have no idea who the editors are, so they are treated exactly as you might be.
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