Self-Guided Walking Tours & Biking Tours

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Discover Florence’s top attractions, including Palazzo Vecchio and Michelangelo’s “David”


  • Walk from the rolling vineyards of Tuscany and into the green heart of Umbria
  • Bask in the sun and villas of Cortona as in the famous book and movie, “Under a Tuscan Sun”
  • Hike through the golden grasslands of the Val d’Orcia to the turquoise waters of Lake Trasimeno
  • Forage for truffles, savor Sangrantino wines and cross the River Tiber to the artistic legacy of Perugia
  • Enjoy short, scenic transfers to discover the very best of southern Tuscany and Umbria on foot

Enjoy the best of Tuscany and the treasures of Umbria on foot, walking from the iconic hilltop towns of Southern Tuscany, into the untouched landscapes of Umbria and to the final highlight of the Renaissance city of Florence.

Staring in Siena, walk through the Val d’Orcia to the hilltop towns of Montepulciano, Pienza, and Montichiello. Wander through landscapes of rolling countryside, rows of Cyprus trees and bountiful olive groves until you reach Cortona, the setting for the popular book and movie, Under a Tuscan Sun. Cross into Umbria and walk the tranquil paths to Perugia, the capital of Umbria, to immerse yourself within the fascinating museums, bustling markets and unspoiled cultural delights.

Toast to your active adventure upon the rooftop terrace of your historic hotel overlooking Florence in celebration of your pilgrimage from Tuscany to Umbria.

Day 1: Arrive Siena 

Start your walking adventure in Siena, a city of extraordinary significance and beauty in southern Tuscany. After checking into your hotel, take a step back in time with a visit to the Piazza del Campo, the heart of Siena, famous for its historic monuments and centuries of Palio horse races (still performed twice every summer in July and August). Stroll the shops and hidden cafés within the nooks of this shell-shaped city for a gelato, aperitif  or grappa to experience the true essence of Italy’s “la vita bella,” (a beautiful life).   

Overnight: Siena

Day 2: Explore Siena & Travel to Montepulciano

The morning is yours to explore the grandeur of the ancient city Siena, a UNESCO World Heritage Site and one of Italy’s must-see attractions. Join a guided tour for a “Taste of Siena,” or set out on your own to explore the Cathedral of Santa Maria Assunta, the Crypt and the Piccolimi Library of the Piazza del Duomo.

In the afternoon, take the train from Siena’s Central Train Station to Montepulciano Stazione (approx. 2 hours, paid locally), where a private transfer will pick you up and take you to your overnight B&B (approx. 30 min). Located in the heart of Montepulciano, this grand home offers a warm welcome to visitors from afar. Enjoy the ornate high fresco ceilings, charming Italian hospitality and a welcome orientation by our local host upon arrival.

Overnight: Montepulciano

Day 3: Walk Pienza to Montichiello & Montepulciano

Today starts with a transfer to Pienza, a stunning hilltop gem that inspired poets, writers and artists of the Renaissance era. Enjoy roaming the cobblestone streets admiring the architecture favored and influenced by Pope Pius II or take a pleasant stroll down the “Via Dell’Amore” (love street), for spectacular views of the Val d’Orcia. 

Sample some Pecorino cheeses, a local delicacy in Pienza, before journeying towards the hamlet of Montichiello. In town, enjoy a light lunch of Ribolitta Italian bean and bread soup or a bruschetta snack at local cafés before continuing along the winding, cypress tree-lined path back to Montepulciano. 

Walk: 9 miles / 14 km

Overnight: Montepulciano 

Day 4: Walk to Aquaviva & Transfer to Cortona

Depart Montepulciano with a short walk through the iconic Tuscan countryside of yellow fields, golden grasslands and hillside villages to Acquaviva. Take an afternoon transfer (approx. 2 hours, departing 1:00 PM) to Cortona. Famous as the setting for the book, “Under the Tuscan Sun” written by Frances Mayes, Cortona continues to be a Tuscan highlight.

Upon arrival, wander the steep and narrow streets to the distinguished Etruscan Academy for its vast collection of bronze and ceramic relics portraying the town’s Etruscan past.

Walk: 6 miles / 10 km

Overnight: Cortona

Day 5: Walk Ossaia to Tuoro & Transfer to Castel Rigone

Take a short transfer to Ossaia, outside of Cortona, for a stunning walk to Tuoro (approx. 10 min). Soak up the spectacular views over the Valdichiana Valley to Lake Trasimeno, known for its beautiful, calm blue waters and the scene from Hannibal’s ambush of the Roman Army in 217 BC (Battle of Lake Trasimeno). 

Cross over into Umbria at the lakeside village of Tuoro to quench your thirst at one of the many terraced osterias (restaurants), with panoramic views of green forest against the glistening blue lake. Continue onward with a private transfer to the 15th century village of Castel Rigone and your overnight accommodation (approx. 20 min).

Walk: 10 miles / 16 km

Overnight: Castel Rigone

Day 6: Transfer to Mongiovino & Walk to Panicale

Take a thirty-minute transfer to Castello di Mongiovino, the starting point of today’s walk to the quaint Umbrian town of Panicale.

Visit the Sanctuary of the Madonna di Mongiovano for divine religious paintings, including the “Virgin with Child,” from notable artists of the Renaissance era before continuing past the castle and down into the small town of Panicale. Stroll through the town’s concentric, ovaled streets to the main piazza for a glass of local Sagrantino wine and a final transfer to your overnight accommodation (approx. 30 min).

Tonight, delight in an included, home-cooked dinner inside this charming old stone house. If desired, a cooking class at this family-run inn can be added upon arrival (arranged and paid locally).

Walk: 7 miles / 12 km

Dinner & Overnight: La Corte del Poggio

Day 7: Wine Tasting & Walk from Monte Vibiano

Enjoy a special, regional wine tasting within the vineyards of Monte Vibiano (approx. 20 mins), the start to this day’s adventure. Tour row upon row of ripened vines (in an electric car), followed by an exclusive wine tasting of local grape varietals and red blends derived from Merlot, Sangiovese, Cabernet and Sagrantino.  

Return on foot via a peaceful stretch of path tracing the Nestore River Park, for yet another delicious, authentic Italian dinner at the country inn, La Corte del Poggio.

Walk: 8 miles / 13 km

Wine Tasting: Monte Vibiano

Dinner & Overnight: La Corte del Poggio

Day 8: Transfer to Monte Tezio & Walk to Perugia

Transfer to Monte Tezio (approx. 40 min), and begin your walk to Perugia along an historic route of the Tezio region. A vital location in the Middle Ages due to its source of drinking water, keep your eyes peeled for the remnants of these ancient aqueducts as you continue towards Perugia.

Upon arrival, walk through Perugia’s giant Etruscan arch gate for a befitting entrance into Umbria’s bustling capital. Cross over the River Tiber and discover the enchanting marketplaces, the Palazzo dei Priori and some of the best museums in Umbria, including the Galleria Nazionale dell’Umbria.

A "Taste of Perugia" guided tour can be arranged for you if you would like to add on an extra day to tour Perugia with the knowledge and expertise of an English speaking, local guide. Tour consists of a food, history and cultural tour (approx. 4 hours, 10 AM - 2 PM, lunch included). Note - Tours are held on Wednesday, Thursday, Friday and Saturday only. Please let us know at the time of booking if you prefer this option (additional costs apply). 

Walk: 11 miles / 18 km

Overnight: Perugia

Day 9: Train to Florence & Discover Florence

Today, take a taxi  from your hotel to the Terontola Train Station to catch a direct train up to Florence (approx. 2.5 hours, please pay locally). Enjoy an epic train ride speeding past captivating Italian landscapes to the Santa Maria Novella station in Florence.

From the Florence train station, take a taxi (or walk) to your nearby hotel to enjoy the rest of the afternoon at your leisure. Discover Florence’s top attractions, including the Palazzo Vecchio, Academia Galleria for Michelangelo’s “David,” and the breathtaking exterior of Florence’s Cathedral “Duomo.”

If desired, private transfers to the Terontola Train Station and from the Florence train station can be arranged for you by your overnight hotel or with Macs Adventure during booking (additional costs apply).

Overnight: Florence

Day 10: Onward Travel

Depending on your travel arrangements, spend the morning exploring more of Florence before departure.

If you need help planning your onward travel, or would like to combine your Italy adventure with our nearby Barolo and Cinque Terre walking tours, please contact us at our office here at Macs Adventure, and we would be more than happy to help.


Included in this trip are 9 nights in hand-selected accommodations to ensure that you enjoy every minute of your stay while in Tuscany and Umbria.

We regularly use the following properties but may accommodate you elsewhere if these are unavailable. 

Single Rooms & Solo Walkers

This trips is based on two people sharing a room. If you’d like separate rooms, a single supplement is required.

If you would like to request a twin room (same room with two separate beds), please notify us at the time of booking so we can request this option.

This trip is also available to solo walkers (a solo supplement is required).


Breakfast is included each morning and consists of a traditional European style breakfast ranging from coffee, tea, yogurt, granola, seasonal fruit, meat, cheese and baked goods. In most cases, a hot dish (eggs and pancakes) will be served a la carte or can be ordered off a menu

Two dinners are included during your stay at the more remote La Corte del Poggio country inn to ensure a special experience and the best of Italian cuisine.

Lunches and all other dinners are not included in this trip, so you are free to choose from nearby available options. We recommend finding cafés or restaurants located in the towns or along the walking route, or you can purchase snacks and a picnic lunch to bring along with you. Further details can be found within your information pack and route notes.

Wine Tour & Cooking Class

A wine tasting is included on the seventh day of this trip and is held at the local winery of Monte Vibiano. Enjoy tasting regional grape varieties and exploring the extensive rows of vineyards by electric car.

An optional cooking class can be added upon arrival on the sixth, or seventh day of this trip at La Corte del Poggio (arranged and paid locally). Enjoy a cooking lesson where Cristina, and her niece, will share with you the secrets of Italian cuisine so that you can replicate the very best, simple recipes back at home.

Additional Nights

You can easily request to add on an extra night at any location during this itinerary.

Please notify us at the time of booking should you wish to add extra nights.







Siena - Hotel Athena

Located inside the ancient city walls of Porta San Marca, the beating heart of Siena, enjoy peace and quiet at the Hotel Athena. Take comfort in your room or relax upon the patio terrace for panoramic, fairytale views.







L'Agnolo B&B - Montepulciano

Montepulciano - L'Agnolo B&B

Located in the center of Montepulciano, this once grand home is now a beautiful, boutique bed and breakfast, still displaying original art from its ornate high fresco ceilings. Admire the town of Montepulciano and the surrounding landscape at this lovely B&B, for an enjoyable holiday in comfort, peace and beauty.







Cortona - Hotel San Michele

Hotel San Michele, located inside the Baldelli Palace, is one of Cortona’s oldest buildings and a declared a national monument by the Ministry of Art. Enjoy a night’s stay in this 15th century mansion located in the core of Cortona.







Castel Rigone - Relais la Fattoria

The beautiful Relais La Fattoria boasts six rooms and an outdoor pool for a cozy, intimate retreat in Umbria. With its canopy patio, lush gardens and ancient castle walls, this 17th century countryside villa is truly a home away from home.







La Corte del Poggio - nr Perugia

Umbria - La Corte del Poggio

Delight in the warm welcome of this old stone house of La Corte del Poggio. This family-run country house has gentle charm where a delicious dinner, and cooking class (reserved and paid locally) and other memorable pleasantries await your arrival.






Perugia - La Locanda della Posta

Discover the best of Perugia within La Locanda della Posta, the only hotel overlooking Corso Vannucci and only a few steps away from monuments and masterpieces of Italian art. Located in one of the most beautiful palaces of the city, enjoy a night of charm and luxury.






Florence - Hotel Cellai

Enjoy this boutique hotel, conveniently located close to the Santa Maria Novella Train Station and within easy reach of Florence’s highlights. Experience life of times past within this 1800 restored palace, where rooms are extremely comfortable, passionately styled and personalized with authentic antiques.


This tour is available to start anytime between mid-April to late-October

As Tuscany and Umbria are very popular destinations, we suggest you book as soon as your plans are finalized to ensure available for specific dates.

When to Go?

The springs months of April, May and June offer warm sunshine, fewer crowds and pleasant conditions. The autumn months of September and October are also a favorite time of year, boasting cooler weather and a striking landscape made up of a yellow, gold and red pallet.

July and August are also great months to go but can very hot for walking. If booking during these months, we therefore advise you to start your walks very early in the morning to avoid the midday heat.


While the route is not waymarked (with the exception of some sections), navigating is easy using the Macs Adventure Navigation App.

Your daily walks will be mapped in the app with GPX tracks, including route notes and turn-by-turn directions. All of these resources are available to download for offline use. More information is outlined within your detailed information pack, in addition to 24/7 telephone support from Macs Adventure should you require assistance.

Grade & Terrain

This tour is graded easy to moderate with six days of walking and a maximum distance of 11 miles. Daily walks average around 6-11 miles (4-6 hours) along rolling terrain as you walk to-and-from hilltop towns.

Most of the route follows farm tracks and dirt trails, while on some days you will be walking along minor country roads with minimal traffic.

You should be in decent physical shape and comfortable walking every day to fully enjoy the walking on this tour.


Our pre-departure information pack has  detailed advice and a packing list on what to bring. This includes warm and cold walking gear, hiking boots, rain gear, day pack and other specifics. 

Luggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 50 lbs. per person.

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. For more information, please visit our travel insurance page by clicking this link.

Getting to Siena

By Air & Train:

Pisa and Florence both have airports with flights from international and national destinations.

We recommend flying into Florence and taking a taxi from the airport to the Florence Train Station. Trains to Siena from Florence depart several times per day (approx. 2 hours total, note—some trains are direct while others have a change over in Empoli).

If flying into Pisa, take the tram from the airport to the Pisa Centrale Train Station. Trains to Siena leave from Pisa Centrale Train Station every 30 minutes (approx. 2 hours total, including one change over along the route).

Prices, ticketing and more information can be found within your pre-departure information pack. For additional information, please check the Trenitalia website for updated timetables.

Getting from Florence

From Florence, buses and taxis connect from the city center to Florence Airport (approx.15-25 min respectively, 20 euros). Or you can take a train to Pisa, Rome or any onward travel destination.


  • 9 Nights in historic hotels and quaint B&Bs
  • 9 Breakfasts
  • 2 Dinners at La Corte del Poggio
  • Wine Tasting
  • Private transfer from Montepulciano Stazione to Montepulciano (Day 2)
  • Private transfers to starting and ending points per the itinerary (Day’s 3-8)
  • Luggage transfers (Day's 4, 5, 6 and 8)
  • Turn-by-turn route notes
  • Detailed information pack
  • Macs Adventure Navigation App
  • 24/7 Telephone Support


  • Flights
  • Travel to Siena (arrival)
  • Travel from Florence (onward travel)
  • Train from Siena to Montepulciano Stazione (Day 2)
  • Train from Perugia to Florence (Day 9)
  • Taste of Perugia Guided Tour
  • Cooking Class
  • Travel insurance
  • Lunches, drinks, snacks and all other dinners
  • Personal equipment


  • Private transfer directly from Siena to Montepulciano (Day 2)
  • Private transfer directly from Perugia to Florence (Day 9)
  • Taste of Siena Guided Tour (Day 2)
  • Taste of Perugia Guided Tour (Day 8)
  • Cooking Class (Day 6)
  • Additional nights before, during or after the trip
  • Single room supplement (if required)
  • Solo supplement (if required)

How fit do I need to be?

This walking holiday is graded easy to moderate and involves 2-4 hours of walking each day so you should enjoy an active lifestyle to get the most from this holiday.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalized. Tuscany and Umbria are extremely popular especially during July/August. You will find up to date availability on our website and we will always try and accommodate your plans so just ask.

What personal equipment do I need?

You will need good walking shoes/boots, comfortable walking clothes, layers, waterproof jacket and pants, a daypack and hats/gloves etc. Our pre-departure information pack will have a detailed list of suggested items to bring.

How do the luggage transfers work? 

When required your bags will be transferred from your hotel and moved onto your next overnight accommodation. This is on Days 4, 5, 6 and 8. When you are traveling with public transport, you will need to take your luggage with you. We ask you to limit your luggage to one bag of up to 50lbs. per person.

Which is the best airport?

Pisa, Florence and Rome all have convenient airports to fly into, and have central train stations in which to arrive and depart. Please take a look at our travel tab for recommended arrival and departure.

What happens if I become ill or can’t walk a stage?

If you are not up for walking the entire route, you can stop at any town along the way and call a taxi, or one of our local representatives, from the contact information found within your pre-departure information pack. If you become ill or want to avoid walking an entire day, that's Ok. Due to being a high tourist destination, local taxis and car services are available to call from your hotel, or you can catch a ride with the morning luggage transfer (when applicable). Specifics and contacts numbers can be found within your pre-departure information pack, or you can ask the host of your overnight hotel for assistance. If you need medical services, please seek immediate assistance at your hotel or nearby hospital.

As always, 24/7 support from Macs Adventure is only a phone call away.

Recommended Reading

Tuscany & Umbria—Lonely Planet Regional Guides

Under The Tuscan Sun—Frances Mayes

Walking and Eating in Tuscany & Umbria—James Lasdun & Pia Davis

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