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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

Contact an Expert

Arrive:

Florence, Italy

Depart:

Florence, Italy

Price: from $5,695

Duration:

8 Days

Departures:

See Dates

Group Size:

5-16

Min Age:

16 yrs

Activity:

Level 2

Easy to moderate hiking on gently rolling terrain for 2-3 hours per day at approximately 1,000-1,500ft. Cultural touring of historic sites includes walking on cobblestone streets.
Learn more here.

Download Detailed Itinerary

Click here to download the Detailed Itinerary.

  • Arrive in Florence

    Day 1

    Welcome to Italy! Meet your group at the Hotel Executive in Florence at 12:30pm and enjoy a light lunch before transferring to the historic wine town of Radda in Chianti. Immerse yourself in the picturesque scenery with a warm-up hike from the castle of San Donato in Perano to the Renaissance Villa Vistarenni. Savor a gourmet dinner with views of Chianti's hills at La Bottega before returning back to Radda for the night.

    Accommodation: Palazzo Leopoldo Dimora Storica & Spa

    Experience old-world charm at the luxurious Palazzo Leopoldo, a converted manor house located in the historic town of Radda in Chianti. Plushly furnished rooms come with top-end amenities and the onsite spa offers a heavenly way to unwind. Clink glasses on the terrace as you soak in the scenic views of Chianti's treasured vineyards.

    Activity: 2 hours/1 miles easy hiking

    Transportation: 1-hour private van transfer

    Meals: Dinner

  • Explore Chianti & Hike Vineyard Trails

    Day 2

    Wake for a day of exploration deep in the heart of Chianti. Marvel at landscapes dotted with vineyards, farmhouses, olive groves, and age-old castles as you drive along Chiantigiana Road. Then take a moderately paced hike through vineyards and fields to the fortified medieval church of San Polo in Rosso. Savor a lunchtime selection of cheeses, bruschette, oils, and homemade pasta prepared by farmer Chez Nicolo before driving to Castellina in Chianti. Here you'll enjoy the botanical wonders of Duccio Fontani's farm, known for its aromatic herbs. Toast your day with a glass of Chianti Classico.

    Accommodation: Palazzo Leopoldo Dimora Storica & Spa

    Experience old-world charm at the luxurious Palazzo Leopoldo, a converted manor house located in the historic town of Radda in Chianti. Plushly furnished rooms come with top-end amenities and the onsite spa offers a heavenly way to unwind. Clink glasses on the terrace as you soak in the scenic views of Chianti's treasured vineyards.

    Activity: 3.5 hours/5 miles moderate hiking

    Meals: Breakfast, Lunch, Dinner

  • Tour Historical Siena & Val d'Orcia

    Day 3

    Journey to the captivating city of Siena for a special guided tour of its historical wonders, including UNESCO-listed Piazza del Campo and the Duomo. Next, enjoy free time to explore the city's beautiful cobblestone streets and charming restaurants on your own. In the afternoon it's off to the pretty hamlet of Pienza and the picturesque Val d'Orcia, famed for its cyprus trees and magnificent golden fields. Learn about Pienza's papal past and take in the sweeping views from your luxury hotel.

    Accommodation: Relais Il Chiostro di Pienza

    Immerse yourself in history at Relais Il Chiostro di Pienza, a former 13th-century Franciscan monastery located in the heart of Pienza. Its 37 comfortable rooms are elegantly furnished and come with convenient amenities. Be wowed by the garden terrace, which affords panoramic views of the valley's romantic rolling hills.

    Transportation: 1.5-hour private van transfer

    Meals: Breakfast, Dinner

  • Hike in Val d'Orcia & Taste Local Cheese

    Day 4

    Start the day with a short visit to Palazzo Piccolomini, a Renaissance wonder built in 1459 as a summer home for Pope Pius II. Next, stop off at Podere Il Casale a few miles west of Pienza to sample fresh pecorino cheese and experience the workings of a biodynamic farm. Follow gently rolling trails back to Pienza and look out for Bagno Vignoni and its famous thermal pool on the way. Tonight, you'll have free time to explore the delights of Pienza.

    Accommodation: Relais Il Chiostro di Pienza

    Immerse yourself in history at Relais Il Chiostro di Pienza, a former 13th-century Franciscan monastery located in the heart of Pienza. Its 37 comfortable rooms are elegantly furnished and come with convenient amenities. Be wowed by the garden terrace, which affords panoramic views of the valley's romantic rolling hills.

    Activity: 4 hours/5 miles easy hiking

    Meals: Breakfast, Lunch

  • Journey to Umbria

    Day 5

    Rise this morning for a pleasant walk up to Monticchiello for a final bird's-eye view of Val d'Orcia. After lunch, travel southeast toward Umbria — the "green and spiritual heart of Italy" known for its classic medieval hill towns and artistic treasures. On the drive you'll see stunning Lake Trasimeno, Italy's fourth-largest lake, surrounded by olive groves and cypress trees. Arrive in the historic walled city of Bevagna, located southwest of Perugia, and enjoy the old-world charm of your luxury hotel.

    Accommodation: L’Orto degli Angeli

    Indulge in warm Italian hospitality at the magnificent L'Orto degli Angeli, a centuries-old residence in beautiful Bevagna. The hotel's 14 traditional suites, across two adjoined palazzos, are richly decorated with original period furnishings and include all the comforts of home. Outside you'll find a pretty garden for al fresco dining.

    Activity: 2 hours/2 miles easy hiking

    Transportation: 1.5-hour private van transfer

    Meals: Breakfast, Lunch, Dinner

  • See Ancient Bevagna & Hike to Montefalco

    Day 6

    Your day begins with a fascinating tour of Bevagna's ancient sites and a visit to a traditional Cartiera, where paper is still produced following age-old techniques. Walk off lunch with a scenic hike across fields and vineyards to the town of Montefalco, known as the " balcony of Umbria." From here you'll enjoy spellbinding views of Spello, Assisi and, in the far off distance, Perugia. Top off the day by tasting the region's signature Sagrantino (Rosso di Montefalco) wine and the ultimate Umbrian delicacy: the black truffle! Return to Bevagna for an evening at your leisure.

    Accommodation: L’Orto degli Angeli

    Indulge in warm Italian hospitality at the magnificent L'Orto degli Angeli, a centuries-old residence in beautiful Bevagna. The hotel's 14 traditional suites, across two adjoined palazzos, are richly decorated with original period furnishings and include all the comforts of home. Outside you'll find a pretty garden for al fresco dining.

    Activity: 3 hours/3.8 miles hiking

    Meals: Breakfast, Lunch

  • Experience the Land of Saints

    Day 7

    Today you'll go deep into the mystical heart of Umbria as you follow in the footsteps of St. Benedict and St. Francis. Starting at Rocca Maggiore, the 800-year-old citadel soaring above Assisi, enjoy a walk down to the pink city admiring panoramic views along the way. In Assisi, visit the Basilica Inferiore and Superiore, home to exquisite frescoes by Giotto. After lunch, take a pilgrimage to Eremo delle Carceri (2,300 feet), a fascinating hermitage complex and the meditation place of St. Francis of Assisi. Tonight, enjoy your farewell dinner back in Bevagna!

    Accommodation: L’Orto degli Angeli

    Indulge in warm Italian hospitality at the magnificent L'Orto degli Angeli, a centuries-old residence in beautiful Bevagna. The hotel's 14 traditional suites, across two adjoined palazzos, are richly decorated with original period furnishings and include all the comforts of home. Outside you'll find a pretty garden for al fresco dining.

    Activity: 2-3 hours/3.1 miles moderate to difficult hiking

    Meals: Breakfast, Lunch, Dinner

  • Return to Florence

    Day 8

    Bid farewell to Italy as you transfer back to Florence airport.

    Transportation: 2.5-hour private van transfer

    Meals: Breakfast

show more

Italy Tuscany and Umbria Walking

Download Detailed Itinerary

Click here to download the Detailed Itinerary.

What to Expect

 

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 Giacon

Silvia was born and raised in Venice, and now lives in the Tuscany region of central Italy. While she is an architect by training, with an MA in History of Architecture, Silvia has more than 20 years of experience as a professional 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 with MT Sobek travelers. Silvia speaks Italian, English, and French.

Alessandro Perrone

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.

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siena - Italy Tuscany and Umbria Walking

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

Trustpilot
  • 2022
  • 2023
  • Go Private
  • Go Custom

2022

The earlier you book, the more choice of available dates you’ll have and once you book, your price is guaranteed.

Scheduled Dates

  • Sep 18 - 25, 2022
    $5,695 price per person dbl occ
    +$700 single supplement
    Available
    Book This Date
  • Oct 09 - 16, 2022
    $5,695 price per person dbl occ
    +$700 single supplement
    Available
    Book This Date

Price Includes

  • Expertise and services of our experienced adventure guides
  • All accommodations as noted in the itinerary
  • All breakfasts, almost all lunches and dinners as noted in the itinerary
  • Snacks and water between meals
  • Additional regional guides and experts where needed
  • Comprehensive Trip Planner with detailed pre-trip information
  • Private guided tours at historic sites, museums, wineries and other select attractions as noted in the itinerary
  • Special events and other select attractions as mentioned in the itinerary
  • All gratuities at hotels and restaurants
  • Equipment and experienced guides for activities as described in the itinerary
  • Park and other entry fees (unless otherwise noted in the Trip Planner)
  • Fares for trains, ferries and other modes of travel as listed in the itinerary
  • Select transfers as mentioned in the itinerary
  • Baggage transfers and porterage

Price Does Not Include

  • International airfare, airport taxes, and excess baggage fees
  • Alcoholic beverages (MT Sobek provides wine at select events)
  • Gratuities for MT Sobek guides and guide-drivers
  • Travel Protection Program
  • Personal expenses
  • Arrival airport transfers

Contact An Expert

800-974-0300

Need help picking your next adventure? Call us to answer your questions.

2023

The earlier you book, the more choice of available dates you’ll have and once you book, your price is guaranteed.

Scheduled Dates

  • May 07 - 14, 2023
    $5,695 price per person dbl occ
    +$700 single supplement
    Available
    Book This Date
  • Sep 03 - 10, 2023
    $5,695 price per person dbl occ
    +$700 single supplement
    Available
    Book This Date
  • Oct 08 - 15, 2023
    $5,695 price per person dbl occ
    +$700 single supplement
    Available
    Book This Date

Price Includes

  • Expertise and services of our experienced adventure guides
  • All accommodations as noted in the itinerary
  • All breakfasts, almost all lunches and dinners as noted in the itinerary
  • Snacks and water between meals
  • Additional regional guides and experts where needed
  • Comprehensive Trip Planner with detailed pre-trip information
  • Private guided tours at historic sites, museums, wineries and other select attractions as noted in the itinerary
  • Special events and other select attractions as mentioned in the itinerary
  • All gratuities at hotels and restaurants
  • Equipment and experienced guides for activities as described in the itinerary
  • Park and other entry fees (unless otherwise noted in the Trip Planner)
  • Fares for trains, ferries and other modes of travel as listed in the itinerary
  • Select transfers as mentioned in the itinerary
  • Baggage transfers and porterage

Price Does Not Include

  • International airfare, airport taxes, and excess baggage fees
  • Alcoholic beverages (MT Sobek provides wine at select events)
  • Gratuities for MT Sobek guides and guide-drivers
  • Travel Protection Program
  • Personal expenses
  • Arrival airport transfers

Contact An Expert

800-974-0300

Need help picking your next adventure? Call us to answer your questions.

Go Private

Go Private

Gather your favorite travel companions to share an MT Sobek adventure on an easy-to-book Private departure.

Choose from the selection of dates below for your group or if your preferred date is not available, we'll create a departure just for you.

Call or email us to get the ball rolling.

*Private trips require a 25% non-refundable deposit.

Private Trip Pricing:

2022 Pricing

5 to 6 guests from $6,295 per person double occupancy

7 to 9 guests from $5,895 per person double occupancy

2023 Pricing

6 to 7 guests from $5,895 per person double occupancy

Additional Costs:

Private pricing excludes potential additional costs such as internal airfare, single supplement, or any park fees that may be required for the trip.

*Private trips require a 25% non-refundable deposit.

Take Over One of These Dates

Make Your Own Dates in These Months

Price Includes

  • Expertise and services of our experienced adventure guides
  • All accommodations as noted in the itinerary
  • All breakfasts, almost all lunches and dinners as noted in the itinerary
  • Snacks and water between meals
  • Additional regional guides and experts where needed
  • Comprehensive Trip Planner with detailed pre-trip information
  • Private guided tours at historic sites, museums, wineries and other select attractions as noted in the itinerary
  • Special events and other select attractions as mentioned in the itinerary
  • All gratuities at hotels and restaurants
  • Equipment and experienced guides for activities as described in the itinerary
  • Park and other entry fees (unless otherwise noted in the Trip Planner)
  • Fares for trains, ferries and other modes of travel as listed in the itinerary
  • Select transfers as mentioned in the itinerary
  • Baggage transfers and porterage

Price Does Not Include

  • International airfare, airport taxes, and excess baggage fees
  • Alcoholic beverages (MT Sobek provides wine at select events)
  • Gratuities for MT Sobek guides and guide-drivers
  • Travel Protection Program
  • Personal expenses
  • Arrival airport transfers

Contact An Expert

800-974-0300

Need help picking your next adventure? Call us to answer your questions.

Go Custom

Create Your Very Own Adventure

Dreaming of an adventure designed exclusively for you? With insider access and decades of experience, our travel experts create custom tailored adventures that are perfect for families, couples, and large groups. MT Sobek's custom adventures are designed to our exacting standards and led by our award-winning adventure guides.

When to start planning? Earlier is always better when designing a custom trip. More time allows for better availability of preferred accommodations, guides and your desired activities. Ideally, start the conversation with us at least 6 months before you want to travel. If you are looking for a custom trip that departs within three months, chances are greatly diminished in securing requested accommodations and the best guides.

*Custom trips require a 25% non-refundable deposit once an itinerary is agreed upon.

Start Planning

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