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Luxury Tuscany Vacation Rental with Guided Walking Tours

Inside Tuscany sunflower iconThis walking tour in Tuscany combines day walks with independent travel, based in a luxurious townhome in the heart of Montepulciano.  This 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.

Contact Us to Book
Trip Length 4 days (or longer if you prefer)
Walking Level Easy to Moderate
Trip Cost From $2175 / person in double occupancy

Walking Levels

Our walks are rated for their level of difficulty as follows:

  • Stroll – Daily distance of 2-5 km (1-3 miles) through archeological sites and in towns with stone stairways. Footwear: Lightweight walking shoes.
  • Easy – Daily distance of 8-10 km (5-7 miles) on dirt paths and gravel roads, with short ascents & descents. Good van access for assistance along the route. Footwear: Sturdy walking shoes.
  • Moderate – Daily distance of 12-16 km (8-10 miles) with longer ascents & descents. May include cobblestone paths and steps, or narrow paths along terraced hillsides. Some van access or options for shorter walks. Footwear: Sturdy walking shoes or lightweight boots.
  • Fitness – Daily distance of 12-16 km (8-10 miles) with steep ascents & descents. Walks are at altitudes of 1200-2450 meters (3500-8000 feet) on trails and forest service roads, some rocky or exposed sections. Limited van access, options for shorter or longer routes. Footwear: Lightweight boots.
old village in Tuscany

Trip Highlights

Can be tailored to suit you

  • Be pampered guests at a luxurious townhome in Montepulciano, and live the Tuscan life
  • Play with a baby cashmere goat at Italy’s only Cashmere goat farm, and enjoy lunch with one of the best views in Tuscany
  • Follow a pilgrim’s route towards Rome, and soak your feet in hot springs favored by St. Catherine
  • Taste prestigious Brunello wine at its source, then listen to monks chant at a 9th-century abbey
  • Enjoy scenic guided walks and visits to exquisite hilltowns, while your late afternoons and evenings are free to explore and dine on your own  – the perfect combination for independent travelers

Trip Details

Choose Your Dates

Florence or Siena

Chiusi train station or car rental

Best Time to Go
Spring, Summer, Fall

Daily breakfast in historic café. All lunches with wine

Luxury townhome

Jump to Itinerary

Day-by-Day Itinerary

Inside Tuscany Placeholder
Inside Tuscany

We can customize this to suit you

Day One

Meet at a centrally located hotel in Florence or Siena.  Head into the lush Chianti area of hills draped in vineyards and take a scenic walk (6 km, 4 miles) along a cypress-lined drive to Radda in Chianti.  Visit a friend’s farm, where a frolicking herd of Cashmere goats provide fiber for hand-woven scarves, shawls and blankets. Enjoy a delicious home-style meal with stunning views. Continue southwards to the stately town of Montepulciano, and check-in to your luxurious townhome.  Stroll through town to choose a friendly trattoria for dinner.

Day Two

Visit the splendid San Biagio church in a panoramic position, before setting off on a peaceful walk past farms and vineyards to the quiet town of Montefollonico.  Meet a small producer of Vino Nobile, and visit his historic 13th century wine cellar, steeped in the heady scent of centuries of wine.  Dine in a welcoming trattoria where the house specialty of fresh pasta tossed in an entire wheel of cheese is a sure fire winner.  After lunch, visit the perfect little town of Pienza, the Utopian dream of Pope Pius ll, that today is lined with shops selling local sheep’s milk cheese and wild boar salami.

Day Three

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.  Travel to the imposing hilltown of Montalcino, perched on a lofty ridge surrounded by the impeccably groomed Brunello vineyards. Enjoy lunch with a tasting of the famed Brunello wine.  This evening 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 Four

Transfer to the Chiusi train station on the Rome-Florence line, or pick up a rental car Mon-Sat. Arrivederci!

Italian Connection

Italian Connection