

Daily Mileage: 4-8 Miles Daily
7 Days
Starting From
$4,848
10 Days
Starting From
$5,798
per person, double occupancy
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Add an ExtensionFar below Mount Subasio’s high slopes glints Assisi’s Basilica, where you recently stood before Giotto’s frescoes of St. Francis preaching to the birds. Just downhill is the hermitage where Francis often meditated, subsisting on roots and sleeping in caves. Thankfully, your prospects today are less austere. In fact, a sumptuous home-cooked lunch awaits in nearby Collepino. Bruschetta, grilled meats and veggies, local wine, and olive oil. This is the flavorful fare you’ve grown accustomed to after days of rambling on this walking tour through Tuscany and Umbria’s hills and vineyards. Central Italy’s beauty will stay with you forever—Siena’s seashell-shaped piazza, Pienza’s harmonious Renaissance architecture—but today’s greatest gift is the blessed sense of peace.
Itinerary
Fri, Jun 3 to Sun, Jun 12 - 2022
Show Itinerary:
All you have to do is get to the airport. On our Flight + Tour Combos, we’ll take care of the rest, handling all the logistics, so you can travel with peace of mind. Spend your first night aloft and arrive refreshed for an unforgettable trip.
Start off your first day in Florence right by having a Country Walkers representative greet you at the airport. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure.
City tour of Siena; 2 hours, easy
After enjoying an included breakfast at your hotel your guides meet you at 9:30 a.m. in the lobby of Hotel de la Ville in Florence. They’ll be wearing Country Walkers shirts. Please be dressed for city walking. Comfortable walking shoes required. (Sneakers are acceptable.)
After meeting in Florence, you travel to Siena. The week begins with a walking tour of the historical center of Siena, an atmospheric Tuscan city. With its mixture of Gothic and Romanesque architecture dramatically set on three hills, Siena rivals Florence not only in beauty but also in culture. Following a light lunch of Sienese specialties, you explore the world-famous Piazza del Campo, presided over by its impressive town hall and tower. The Campo is the setting of the celebrated Palio horse race. Your engaging local guide leads you to the Duomo, the town’s main cathedral, to view its striking marble façade.
Later, you drive to San Quirico d’Orcia, one of the pilgrimage routes that connected northern Europe to Rome, and your home for the next three nights. An important stop during medieval times along the Via Francigena, San Quirico is a charming, walled, hilltop town surrounded by vineyards that produce three great Tuscan wines: Montepulciano, Brunello, and the Orcia DOC. Magnificent medieval architecture adorns its streets, and your boutique hotel is located just outside one of the town gates. A warm, wood-beamed restaurant in the heart of town welcomes you to dinner. Here, a glass of Brunello paired, perhaps, with a bistecca fiorentina (local grilled beef) is the perfect start to the week’s culinary delights.
Included Meals: Breakfast, Lunch, Dinner
6 miles, easy to moderate; optional 2-3 miles, easy to moderate
Today’s exploration begins on the outskirts of San Quirico. After an initial short drive to the village of Torrenieri, step onto a dirt lane that meanders along rolling terrain between the Orcia Valley and the Crete Senesi (Sienese hills) toward Pienza, the morning’s destination.
Lunch awaits at an old Tuscan farmhouse, where your hosts welcome you with an assortment of local pecorino (sheep’s milk cheese), cold cuts, and homemade preserves and pickles accompanied by their house wine. After lunch, you are driven a few minutes away to Pienza, the birthplace of Enea Silvio Piccolomini, elected Pope Pius II in 1458. Envisioning the creation of the “ideal Renaissance town,” Pius II had the village renamed and entirely redesigned by Florentine architect Bernardo Rossellino. The village’s restructuring came to a halt following Pius II’s death, and the only part of the urban plan that had been completed was the town center, Piazza Pio II. Here, the main monuments lie harmoniously along the town’s central axis, with the town hall opposite a 15th-century cathedral.
An optional afternoon walk departs from the tiny spa village of Bagno Vignoni, where you can soak your feet in the warm waters flowing out of the town’s picturesque main square. This pool is the only one in Italy that is, in fact, a thermal pool. After returning to the hotel in San Quirico, you have time to relax before enjoying dinner on your own at one of the fine local eateries in town, with recommendations from your guides.
Included Meals: Breakfast, Lunch
4-7 miles, easy to moderate
Today you depart San Quirico and walk through gentle hills in the shade of old-growth woods, skirting vineyards where the famous Sangiovese Grosso grape is grown for the world-famous Brunello wine. You might stop to visit an ancient Etruscan settlement, still under excavation. Then continue through farmland, ancient dwellings, wineries, and olive groves before making the dramatic descent to the isolated Romanesque Abbey of Sant’Antimo.
You continue on to the attractive hilltop town of Montalcino, where you have time to stop into one (or more!) of the town’s enoteche (wine bars) or restaurants, for a tasting and lunch on your own. Stroll through town, perhaps shopping for local products, perusing galleries, or snapping photos from the ramparts of the Rocca (the 14th century fortress that affords views towards Monte Amiata, Siena, and the hills of Maremma), before a mid-afternoon return to San Quirico. You have time to explore or relax (or perhaps indulge in a spa treatment at your hotel’s nearby sister property) before gathering for dinner. You may want to step out for a pre-dinner stroll and a visit to the Horti Leonini—a wonderful example of classic Italian-style gardens, built by Diomede Leoni in 1540. This evening, reunite with your guides and fellow travelers for a casual meal at a local osteria.
Included Meals: Breakfast, Dinner
3 miles, easy; optional 3-4 miles, easy to moderate
This morning you bid farewell to southern Tuscany as your drive winds through the rolling hills and medieval hilltop villages of the Crete Senesi, descends on the plains surrounding Lake Trasimeno, and enters the central valley of Umbria, a region known as the “Green Heart of Italy.”
Your morning is devoted to an exploration of Assisi. This stunning town sits in a commanding position on the slopes of Mount Subasio and has retained its charming medieval qualities and strong associations with St. Francis. The intriguing history of Assisi’s city center and the Basilica of St. Francis come to life with interpretation from your guide. Afterward, enjoy lunch at a local restaurant.
The afternoon offers several options. You may travel to Spello, your home for the next three nights, to stroll its picturesque alleys or relax by the hotel pool or in the hammam (Turkish bath).
Alternatively, an easy walking option is offered—leading out of Assisi into the lush, surrounding countryside and olive groves all the way back to Spello. Enjoy an independent dinner this evening at your hotel’s restaurant or at one of the charming trattorias in town. (Your guides will provide recommendations.)
Included Meals: Breakfast, Lunch
5-7 miles, easy to moderate
After breakfast, depart for Gubbio, the medieval masterpiece of Umbria that charms with its intimate alleys and surprisingly spacious panoramic piazza, flanked by the stunning palazzo comunale. Following a scenic drive, the morning walk’s destination is the Church of Saint Ubaldo, perched high on the mountainside overlooking Gubbio. The church is the endpoint of the annual “Race of the Ceri,” a colorful historical festival where locals race ceri (giant heavy wooden structures that resemble candlesticks). The walking route passes by limestone outcrops and a tiny chapel, then meanders through woods, along a creek, and up a narrow gorge. After visiting the church and admiring the three ceri contained within, enjoy a scenic funicular ride descending into town, where you are free to explore (and refuel!) savoring lunch at an osteria of your choosing. After lunch, you return to Spello, with an optional walk en route that traces ancient oak-lined farm roads leading all the way to the hotel. Your guides provide ideas for dinner on your own in town; many restaurant and trattoria menus offer typical dishes such as chickpea soup drizzled with olive oil, bruschetta, or strangozzi, the regional square-shaped ribbon pasta (literally shoestring-like).
Included Meals: Breakfast
5-9 miles, easy to moderate
After breakfast, you embark on a short drive to the Natural Park of Mount Subasio, a protected area with serene paths meandering through open meadows and oak and pine woods. Mount Subasio is the sprawling mountain on whose flank Assisi is built. A haven of subtle beauty and spirituality, it was here that St. Francis preached to the birds as they gathered on tree branches.
Hiking in the meadows along the summit of the mountain, you are likely to see grazing herds of sheep, white Chianina cows, and semi-wild horses before descending to lunch in the small, charming hamlet of Collepino. The waiting table is spread with an ample antipasto of assorted bruschetta, followed by grilled meats and vegetables.
After lunch, you may choose to return to Spello by van or descend on foot, continuing through olive groves and alongside an ancient Roman aqueduct. This aqueduct once brought drinking water into town along the eastern side of the mountain.
This evening’s farewell dinner is at an extraordinary venue in Assisi: a restaurant built on top of a glassed-in site of remarkable Roman ruins. You dine on the finest local cuisine and toast your week’s adventures with a glass from the restaurant’s world-class wine cellar.
Included Meals: Breakfast, Lunch, Dinner
After a leisurely breakfast, you depart Spello for Rome. Time and weather permitting, a brief stop en route in the walled medieval hill town of Spoleto may allow for a walk and view from the impressive Ponte delle Torri (Tower Bridge). You arrive early afternoon to Rome for your post-tour night.
The rest of the day is yours to enjoy at your leisure—perhaps explore the city, rest up in the hotel, or select a local restaurant for lunch and dinner. We provide detailed city information to help you plan your day.
Included Meals: Breakfast
After an included breakfast this morning, complimentary transportation is provided to Rome’s Leonardo da Vinci Airport based on your departure time.
Included Meals: Breakfast
Sun, Jun 5 to Sat, Jun 11 - 2022
Show Itinerary:
2 hours, easy walking tour of Siena
Your guides meet you at 9:30 a.m. in the lobby of Hotel de la Ville-Piazza Antinori, 1 in Florence. They’ll be wearing Country Walkers shirts. Please be dressed for city walking. Comfortable walking shoes required. (Sneakers are acceptable.)
After meeting in Florence, you travel to Siena. The week begins with a walking tour of the historical center of Siena, an atmospheric Tuscan city. With its mixture of Gothic and Romanesque architecture dramatically set on three hills, Siena rivals Florence not only in beauty but also in culture. Following a light lunch of Sienese specialties, you explore the world-famous Piazza del Campo, presided over by its impressive town hall and tower. The Campo is the setting of the celebrated Palio horse race. Your engaging local guide leads you to the Duomo, the town’s main cathedral, to view its striking marble façade.
Later, you drive to San Quirico d’Orcia, one of the pilgrimage routes that connected northern Europe to Rome, and your home for the next three nights. An important stop during medieval times along the Via Francigena, San Quirico is a charming, walled, hilltop town surrounded by vineyards that produce three great Tuscan wines: Montepulciano, Brunello, and the Orcia DOC. Magnificent medieval architecture adorns its streets, and your boutique hotel is located just outside one of the town gates. A warm, wood-beamed restaurant in the heart of town welcomes you to dinner. Here, a glass of Brunello paired, perhaps, with a bistecca fiorentina (local grilled beef) is the perfect start to the week’s culinary delights.
Included Meals: Lunch, Dinner
6 miles, easy to moderate; optional 2-3 miles, easy to moderate
Today’s exploration begins on the outskirts of San Quirico. After an initial short drive to the village of Torrenieri, step onto a dirt lane that meanders along rolling terrain between the Orcia Valley and the Crete Senesi (Sienese hills) toward Pienza, the morning’s destination.
Lunch awaits at an old Tuscan farmhouse, where your hosts welcome you with an assortment of local pecorino (sheep’s milk cheese), cold cuts, and homemade preserves and pickles accompanied by their house wine. After lunch, you are driven a few minutes away to Pienza, the birthplace of Enea Silvio Piccolomini, elected Pope Pius II in 1458. Envisioning the creation of the “ideal Renaissance town,” Pius II had the village renamed and entirely redesigned by Florentine architect Bernardo Rossellino. The village’s restructuring came to a halt following Pius II’s death, and the only part of the urban plan that had been completed was the town center, Piazza Pio II. Here, the main monuments lie harmoniously along the town’s central axis, with the town hall opposite a 15th-century cathedral.
An optional afternoon walk departs from the tiny spa village of Bagno Vignoni, where you can soak your feet in the warm waters flowing out of the town’s picturesque main square. This pool is the only one in Italy that is, in fact, a thermal pool. After returning to the hotel in San Quirico, you have time to relax before enjoying dinner on your own at one of the fine local eateries in town, with recommendations from your guides.
Included Meals: Breakfast, Lunch
4-7 miles, easy to moderate
Today you depart San Quirico and walk through gentle hills in the shade of old-growth woods, skirting vineyards where the famous Sangiovese Grosso grape is grown for the world-famous Brunello wine. You might stop to visit an ancient Etruscan settlement, still under excavation. Then continue through farmland, ancient dwellings, wineries, and olive groves before making the dramatic descent to the isolated Romanesque Abbey of Sant’Antimo.
You continue on to the attractive hilltop town of Montalcino, where you have time to stop into one (or more!) of the town’s enoteche (wine bars) or restaurants, for a tasting and lunch on your own. Stroll through town, perhaps shopping for local products, perusing galleries, or snapping photos from the ramparts of the Rocca (the 14th century fortress that affords views towards Monte Amiata, Siena, and the hills of Maremma), before a mid-afternoon return to San Quirico. You have time to explore or relax (or perhaps indulge in a spa treatment at your hotel’s nearby sister property) before gathering for dinner. You may want to step out for a pre-dinner stroll and a visit to the Horti Leonini—a wonderful example of classic Italian-style gardens, built by Diomede Leoni in 1540. This evening, reunite with your guides and fellow travelers for a casual meal at a local osteria.
Included Meals: Breakfast, Dinner
3 miles, easy; optional 3-4 miles, easy to moderate
This morning you bid farewell to southern Tuscany as your drive winds through the rolling hills and medieval hilltop villages of the Crete Senesi, descends on the plains surrounding Lake Trasimeno, and enters the central valley of Umbria, a region known as the “Green Heart of Italy.”
Your morning is devoted to an exploration of Assisi. This stunning town sits in a commanding position on the slopes of Mount Subasio and has retained its charming medieval qualities and strong associations with St. Francis. The intriguing history of Assisi’s city center and the Basilica of St. Francis come to life with interpretation from your guide. Afterward, enjoy lunch at a local restaurant.
The afternoon offers several options. You may travel to Spello, your home for the next three nights, to stroll its picturesque alleys or relax by the hotel pool or in the hammam (Turkish bath). Alternatively, an easy walking option is offered—leading out of Assisi into the lush, surrounding countryside and olive groves all the way back to Spello. Enjoy an independent dinner this evening at your hotel’s restaurant or at one of the charming trattorias in town. (Your guides will provide recommendations.)
Included Meals: Breakfast, Lunch
5-7 miles, easy to moderate
After breakfast, depart for Gubbio, the medieval masterpiece of Umbria that charms with its intimate alleys and surprisingly spacious panoramic piazza, flanked by the stunning palazzo comunale. Following a scenic drive, the morning walk’s destination is the Church of Saint Ubaldo, perched high on the mountainside overlooking Gubbio. The church is the endpoint of the annual “Race of the Ceri,” a colorful historical festival where locals race ceri (giant heavy wooden structures that resemble candlesticks). The walking route passes by limestone outcrops and a tiny chapel, then meanders through woods, along a creek, and up a narrow gorge. After visiting the church and admiring the three ceri contained within, enjoy a scenic funicular ride descending into town, where you are free to explore (and refuel!) savoring lunch at an osteria of your choosing. After lunch, you return to Spello, with an optional walk en route that traces ancient oak-lined farm roads leading all the way to the hotel. Your guides provide ideas for dinner on your own in town; many restaurant and trattoria menus offer typical dishes such as chickpea soup drizzled with olive oil, bruschetta, or strangozzi, the regional square-shaped ribbon pasta (literally shoestring-like).
Included Meals: Breakfast
5-9 miles, easy to moderate
After breakfast, you embark on a short drive to the Natural Park of Mount Subasio, a protected area with serene paths meandering through open meadows and oak and pine woods. Mount Subasio is the sprawling mountain on whose flank Assisi is built. A haven of subtle beauty and spirituality, it was here that St. Francis preached to the birds as they gathered on tree branches.
Hiking in the meadows along the summit of the mountain, you are likely to see grazing herds of sheep, white Chianina cows, and semi-wild horses before descending to lunch in the small, charming hamlet of Collepino. The waiting table is spread with an ample antipasto of assorted bruschetta, followed by grilled meats and vegetables.
After lunch, you may choose to return to Spello by van or descend on foot, continuing through olive groves and alongside an ancient Roman aqueduct. This aqueduct once brought drinking water into town along the eastern side of the mountain.
This evening’s farewell dinner is at an extraordinary venue in Assisi: a restaurant built on top of a glassed-in site of remarkable Roman ruins. You dine on the finest local cuisine and toast your week’s adventures with a glass from the restaurant’s world-class wine cellar.
Included Meals: Breakfast, Lunch, Dinner
After a leisurely breakfast, you depart Spello for Rome. Time and weather permitting, a brief stop en route in the walled medieval hill town of Spoleto may allow for a walk and view from the impressive Ponte Delle Torri (tower bridge). You arrive at Roma Termini (Rome’s central train station) at approximately 1:30 p.m. Here, you bid farewell to your guides and make connections for onward travels.
Included Meals: Breakfast
Hotel De La Ville
This hotel has been completely restored and sits in a convenient location in the heart of Florence, a few steps from the famous Duomo on the fashionable shopping street Via Tornabuoni, which is closed to car traffic and quiet. Enjoy spacious, comfortable, air-conditioned private rooms.
Villa del Capitano
Breathtaking views of the Val d’Orcia await you at the renovated Villa del Capitano. Located near San Quirico’s medieval walls, the hotel features bright, air conditioned rooms and contemporary designs. Part of a family-owned collection of properties, this historical villa prides itself on its authentic cuisine, from hearty breakfast buffets to a duo of restaurants serving traditional and innovative dishes featuring fresh, local ingredients. Enjoy access to the outdoor pool and spa at a nearby sister property, and perhaps raise a glass of Brunello in the villa’s cozy bar.
Hotel La Bastiglia
Located in a former 16th-century grain mill in the walled, medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiana Valley. Well-appointed rooms include WiFi and air conditioning, and the on-site restaurant boasts a prestigious wine cellar. Indulge the hotel’s spa services including a private hammam, massage chairs, a choice of massage offerings. Or, perhaps, relax with a dip in the outdoor swimming pool.
Hotel dei Mellini
Located on the west bank of the Tiber River near the Spanish Steps, the Piazza Navona, and the Vatican this elegant city-center hotel offers access to Rome’s monuments, shopping, and dining. Guestrooms and public spaces boast the classic Umbertino style of 19th-century Italy, with tastefully updated rooms, a beautifully landscaped rooftop patio, and a modern gym. Amenities include air conditioning, free WiFi, in-room massage services, and complimentary use of bicycles.
2022 Pre-Tour Extension - Florence
2 Nights From $448
per person, double occupancy
Single Supplement: From $298
All you have to do is get to the airport. On our Flight + Tour Combos, we’ll take care of the rest, handling all the logistics, so you can travel with peace of mind. Spend your first night aloft and arrive refreshed for an unforgettable trip.
Start off your first day in Florence right by having a Country Walkers representative greet you at the airport. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure.
After a delicious included breakfast at your hotel, you are free to explore on your own, using our included city information packet to guide your discoveries.
Included Meals: Breakfast
After a delicious included breakfast at your hotel, you are free to explore on your own, using our included city information packet to guide your discoveries.
Included Meals: Breakfast
2022 Post-Tour Extension - Rome
2 Nights From $348
per person, double occupancy
Single Supplement: From $298
After a delicious included breakfast at your hotel, you are free to explore on your own, using our included city information packet to guide your discoveries.
Included Meals: Breakfast
After a delicious included breakfast at your hotel, you are free to explore on your own, using our included city information packet to guide your discoveries.
Included Meals: Breakfast
After an included breakfast this morning, complimentary transportation is provided to Rome’s Leonardo da Vinci Airport based on your departure time.
Included Meals: Breakfast
What's Included | Flight + Tour Combo | Tour Only |
---|---|---|
Exceptional boutique accommodations | ||
13 on-tour meals: 6 breakfasts, 4 lunches, 3 dinners | ||
Local guides with you throughout tour | ||
Local wine and/or beer with dinner | ||
Entrance fees and special events as noted in the itinerary | ||
Travel assistance available 24/7 provided by Allianz Global Assistance | ||
Telescopic walking sticks provided on tour | ||
Roundtrip airfare | ||
One extra night in Florence and one extra night in Rome | ||
Airport car service for arrival & departure | ||
Pre- and post-tour breakfasts | ||
Business-class upgrades available |
Dates & Prices
Departing Airport :
Select Year :
Flight + Tour Combo
10 days, includes round-trip international airfare , airport shuttle, and additional hotel nights with included breakfast.
Single Supplement: From $798
Fri, Oct 14 - Sun, Oct 23, 2022
From
$5,798
Per person, double occupancy
Reserve OnlineSelect Year :
Tour Only
7 Days. Includes walking vacation only.
Single Supplement: From $548
For more information, call: 800-245-3868
Please note: Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. Prices include all airline surcharges and Government taxes and fees. Ask our Tour Consultants for details. Every effort has been made to produce this information accurately. We reserve the right to correct errors. Prices are based on preferences selected above, including meals and sightseeing as specified in What’s Included. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only.
The hill towns, far from the crowds of Rome and Florence, gave us an in depth view not only into the history of the places we visited but also of life in them today. Our guides brought into focus both the old and the new.
Bill28, Virginia
Italy: Tuscany & Umbria
Where do you start! Everything about the trip was well thought out and planned thoroughly. Guides were excellent, food was good. Many unique and memorable experiences. Recommend this tour to anyone with interest in this area. No regrets...many memories.
Joanne, Mandeville, LA
Italy: Tuscany & Umbria
Experience your destination like an insider with people who call it home.
Manuela Ciri
Manuela Ciri was born and raised on a farm in Umbria where she continues lead cooking lessons and olive oil tastings. Educated both in Italy and in the US, she is a botanist, herbal healer, and certified environmental guide. Her vast knowledge of nature, agriculture, and traditional food is warmed by her sunny smile and joyful nature. When not guiding, she teaches environmental education in public schools, works on landscape engineering projects, or can be found scouting new trails around the mountains and hills of central Italy.
Alessandro Gullo
Alessandro Gullo has Sicilian ancestry and was educated in the US as well as Italy. He is a certified guide of historic monuments who effortlessly combines his charming personality with a vast knowledge of the culture, art, history, food, and wine of Italy.
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