Walking tour in Tuscany HilltownsWine tasting  in Tuscany


About Our Trips

2-3 Day Tours

1-Day Tours

Private Tours

Emanuele's Kitchen



6 days

Walking Level: Easy




Chiusi train station

Dates & Guaranteed Price

See Calendar

Single Supplement

$860 USD


Daily breakfast

4 lunches with wine

4 dinners with wine

Maximum Participants



Luxury inns and boutique hotels




View Map Detail
“We loved our recent Tuscany Hilltowns trip. We rate it a ‘10 out of 10!’ ”

– L.G., U.S.A.



Tuscan Bread Salad



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Tuscan wine tourThis exceptional walking tour combines the exclusive finds gleaned from our years of living and working in Tuscany with the unmatched beauty of Tuscany’s finest hilltowns and pristine landscape. Even in high season, our carefully chosen walking trails are blissfully free of tourists, and our many friends along the way treat us all like family. Enjoy a rare opportunity to dine in the home of a local friend, who also happens to be a great cook.


Meet our Tuscan friends and be invited to dinner in a beautifully restored farmhouse
Be pampered guests at a luxurious boutique hotel near Pienza, and live the Tuscan villa life
Quaff fine Chianti Classico in a cool, dark wine cellar beneath a 14th-century castle in Volpaia
See Siena with a native guide, visit the magnificent Duomo and learn the secrets of betting on race horses during the Palio
Comb a cashmere goat at Italy’s only Cashmere goat farm, and soothe your skin with a goat’s milk balm
Follow a pilgrim’s route towards Rome, listen to the monks chant at a 9th-century abbey, soak your feet in hot springs favored by St. Catherine


Day One

SpacerTomato Bruschette
 Bruschetta al Pomodoro

Morning rendezvous in Florence and travel to the beautiful Chianti wine country. Enjoy a delicious Tuscan lunch before setting off on our 8 km (5 mile) walk along cypress-lined drives past magnificent villas and rustic farmhouses to the pretty village of Radda in Chianti. We stay in a beautifully renovated town palazzo in the center of charming Radda in Chianti. Tonight we dine in a favorite country restaurant where classic dishes are served with Tuscan flair.

Day Two

Today’s panoramic 14 km (8.5 mile) walk wanders through peaceful farmland past a 12th-century church surrounded by Sangiovese vineyards and on to a tiny hilltop village devoted to wine and olive oil production. A private tasting of Chianti Classico and Super Tuscan vintages is followed by an explanation of the merits of extra virgin olive oil and a visit to an olive oil mill. We depart with new knowledge of the world’s best olive oil and no chapped lips! Free evening for dinner.

Hilltown Siena Tuscany cathedral Spacer
Il Duomo 

Day Three

We head south to the magnificent city of Siena where a local guide gives us a walking tour through the historic center of town. Free time to lunch and explore on your own. Leaving Siena, we return to Radda and visit a friend's nearby farm, where a herd of Cashmere goats provide milk for unique cosmetic products and fiber for hand-woven scarves, shawls and blankets. Tonight Italian amici invite us to their house for a welcoming and delicious home-style meal.

Day Four

We travel to the imposing hilltown of Montalcino, perched on a lofty ridge surrounded by the impeccably groomed Brunello vineyards. Our peaceful walk follows an old Roman cart track for 13 km (8 miles) through woodlands and past rustic villages to the exquisite 9th century church of Sant’Antimo, set in perfect harmony with the surrounding landscape. After visiting the church, we transfer to our hotel, a beautifully renovated country inn with sumptuously appointed rooms. This evening we dine in an inviting ristorante acclaimed for its innovative pasta and delectable dolci, so settle down to a leisurely meal in one of Tuscany’s top restaurants.

Day Five

SpacerMontepulciano hilltown Tuscany
 La Bella Toscana

We begin in the perfect village of Pienza, perched on a clifftop and built of golden stone, which was originally designed as the Utopian dream of Pope Pius II. Today it is renowned for its pecorino, a pungent cheese made from sheep’s milk, which we’ll be sure to sample at lunch. Our 17 km (10.5 mile) walk follows quiet farm roads with sweeping views across the soft undulating hills of the lovely Orcia valley. We visit the charming village of Monticchiello before reaching our destination, the dignified city of Montepulciano, proud home to the Vino Nobile produced on the surrounding slopes. Farewell dinner in a lively family-run trattoria where special Tuscan dishes are prepared just for us.

Day Six

Visit the charming village of San Quirico and walk 6 km (3.5 miles) to Bagno Vignoni, known for its hot springs since Roman times. After a light lunch of bruschetta anointed with the best extra virgin olive oil and a variety of local cheeses, we transfer to the Chiusi train station on the Rome-Florence line. Arrivederci!

If “Tuscany Hilltowns” interests you, consider similar trips like La Maremma Walk or Piedmont Vineyards & Lakes.

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