Italy Tuscany and Umbria Walking

Sweeping Tuscan Landscapes, Mystical Umbria & Historic Siena

Discover the enchanting landscapes of central Italy on this delightful walking journey from the age-old vineyards and villages of Chianti to historic Siena, Pienza, and Bevagna. Savor the delicate aroma of wild lavender as you follow expert guides on lesser-known paths and feast on sumptuous farm-to-table fare prepared in traditional kitchens. In Umbria, Italy's green and spiritual heart, you'll move amidst artistic and architectural treasures, and follow in the footsteps of St. Francis of Assisi. Top it off with black truffles, fine wines, and nights at luxurious historic hotels. This trip is beyond special!

Step through a wonderland of vineyards, lavender fields, and picturesque hilltop villages

Marvel at the cultural wonders of Siena, ancient Pienza, and the Land of Saints

Indulge in local farm-to-table fare and enjoy tranquil stays at exquisite historic hotels

Why take this trip with us?

Reason #01

This perfectly paced weeklong adventure blends active hiking and cultural immersion, getting you to the heart of Tuscany and Umbria.

Reason #02

Our hiking adventures in Italy benefit from over 40 years of continuous refinement and offer local guides that quickly connect you to the heart of the region.

Reason #03

You'll enjoy genuine experiences, from local-favorite restaurants and working farms to family-run wineries and historic hotels, so you can enjoy every moment.

Meet your guides

Silvia Giacon

Silvia is an Italian born and raised in Venice. Now she permanently lives in Tuscany. While she is an architect by training and has a master in history of Architecture, she has over 20 years of professional experience as Trip Leader. She lived in Toronto, Canada for over a decade and, since then, she has led both walking and bicycle trips throughout Europe. Now she guides trips in Tuscany and southern Italy sharing her passion for her Country. Languages spoken: Italian, English, French.

Alessandro Perrone

Born and raised in Puglia, Alessandro has expert knowledge of this Mediterranean region, known as the "heel of Italy's boot" and is a fully licensed tour guide, food lover, olive oil taster, wine sommelier, and naturalistic guide. Known for his empathic personality and enthusiasm for his profession, Alessandro is the perfect host to share with you the beauty, the flavors and the soul of beautiful Puglia.

Activities

Leisurely hiking for 2-3 hours per day on gently rolling terrain. Cultural touring with stops at historic sites, farms, and wineries.

Lodging

Luxury historic hotels, including a former monastery and a 15th-century palazzo, with comfortable en-suite rooms and modern amenities.

Climate

May, June, and October have higher chances of precipitation, while summer months are dry and warm. July is the warmest months with temperatures in the 80's. August and September are pleasant with temperatures in the upper 60's and 70's.

FAQ

Is this a hardcore hiking trip?

No. All of our trips are active, and therefore you should be comfortable walking in the outdoors up to 3 hours on varying terrain, including cobblestone, unpaved roads, and vineyards.

Can I skip a day, if I am tired?

Yes. You are always welcome to skip a day to relax or explore on your own. On some days, you will need to transfer to our next accommodation.

Do I need hiking boots for this trip?

No. The best footwear for this trip would be cross-training shoes or low-ankle hiking or walking shoes.

I am gluten intolerant. Will I be able to find enough meal choices and variety of foods on this trip?

Yes. Tuscany and Umbria have plenty of options for gluten free, delicious food.

Is Wi-Fi available at all of the hotels?

Yes, you will have access to Wi-Fi every day, if you choose.

Are dinners formal?

No. Lunches are casual, and dinners are smart casual.

Testimonials

"We have traveled throughout the world, but never experienced a level of service and attention to detail as we did with MT Sobek."

Dennis G.
MT Sobek Guest

"I've taken six MT Sobek trips and they have all exceeded my expectations. The staff, the food, the logistics and the communications have always been exceptional. Thank you for being my "go to" adventure travel company!"

Margaret I.
MT Sobek Guest