• NEW! Treasures of Tuscany and Umbria

    Discover the Artistic & Spiritual Heart of Italy

    Experience the full bounty of "la dolce vita," from the must-see cities of Florence and Siena to postcard-perfect Val d'Orcia. You'll hike among rolling hillside vineyards and drink in the blissful ambiance of Italian country life, and discover the medieval hilltowns of Umbria. With every step, you'll feel the real heartbeat of Italy!

    best times to go: June, September

    departures: No group departures scheduled. Private departures are available on the dates of your choice, pending availablity. Call us for details.

    pricing: from $4,995 see detailed pricing

    The Mediterranean

    Easy to Moderate
Also great as a private trip. Call for details

Discover the Artistic & Spiritual Heart of Italy

In Europe, living well is nearly an art form. And nobody does it quite like the Italians! History and spirit meet with the land to create a vibrant nation of warmth and brio—an exuberance and love of life you can’t help but fall in love with. We’ve chosen two of our favorite regions to showcase this enviable talent: Tuscany, amazing for its light and for the landscapes crafted by generations of toiling Tuscans (it is, some say, simply perfect); and Umbria, considered the spiritual heart of Italy, close to Tuscany geographically, but culturally and historically unique.

Our adventure here introduces you to the best of both: the historical and visual, the cultural and aesthetic, plus the gustatory delights of the celebrated food and wine—all in the company of expert guides who would like nothing better than to show you the region they call home.


9 Days moderate hiking on hilly and uneven terrain


  • Discover the seductive charms of Tuscany's iconic villages, including Florence, Siena, San Gimignano, and Montalcino
  • Enjoy classic Chianti region and explore the never ending hills of Val d'Orcia
  • Explore the historic medieval hill towns of Umbria, including Montefalco, Spoleto, and Assisi
  • Sip fine wines, taste handcrafted olive oils, and feast on regional culinary delights

Duration: 10 days Start Location: Florence End Location: Florence

Download Detailed Itinerary
  • Itu_rfs_01
    Day 1 : Arrival in Florence – Greve in Chianti

    Plan to arrive in Florence Italy on or before day 1.  We’ll meet with our trip leader and the rest of the group at 1:30 p.m. at the Hotel Villa Batania, about a 20-minute taxi ride from the airport. After a short trip orientation, we’ll drive to the hills of southern Chianti to Greve in Chianti. Toward the end of the Middle Ages many people came to this area to establish new homes around the market area that later became the town of Greve. Today, Greve is the wine capital of the region. From here we’ll take a walk to Lamole, a hilltop village overlooking the valley. Lamole was once one of the strongest fortified places of the Greve Valley.After a delicious dinner and a tasting of Chianti Classico “Gallo Nero”, we’ll return to Florence. (2 hours hiking.)

  • Bigstock-san-gimignano
    Day 2 : Colle Val d’Elsa – San Gimignano

    Today we'll transfer to the walled medieval town of Colle Val d’Elsa, renowned as the heart of the crystal industry in Italy. We'll take a walking tour of the old part of town visiting the best crystal maker shops. From Colle Val d’Elsa, we’ll take a pleasant walk toward San Gimignano. We’ll enjoy lunch near San Gimignano and take a tour of this small romantic old town with its 13 towers that remain from medieval times. The cathedral contains precious frescoes by Ghirlandaio illustrating the life of Santa Fina, the patron Saint of San Gimignano. Afterwards, we'll drive to San Lucchese, a small village above Poggibonsi, to stay at the Hotel Villa San Lucchese, a beautifully restored 16th-century villa with a beautiful garden and year-round swimming pool. (3 hours hiking.)

  • Itu_fam_tuscanvillage
    Day 3 : Volterra

    Volterra (ancient Velhri) was one of the 12 city-states of the Etruscan nation and has been famous for alabaster working since the fourth and fifth centuries b.c. We'll have a chance to visit a contemporary alabaster workshop and the superb Museum Guarnacci, which hosts one of the most important collections of Etruscan art, most notably the spectacular “Deposition” by Rosso Fiorentino (1495–1540). We’ll then transfer to Val di Cecina and hike around the area of the “Saline di Volterra,” a place where salt was extracted in ancient times. It’s a reminder that salt was considered one of the most precious riches during the Middle Ages. (3–4 hours hiking.)

  • Bigstock-piazza-del-campo-with-palazzo--27274433
    Day 4 : Siena

    After breakfast, we'll transfer to Siena for a guided tour of this beautiful medieval city, the eternal rival of Florence. We'll see how the traditional neighborhood affiliations (Contrade), dating back to ancient times, are still an important part of contemporary life, culminating in the impressive “Palio,” the famous horse race. We’ll tour the main sites, ending the visit in the central piazza, Il Campo, for lunch on your own and some time to do a little shopping (Siena is known for its beautiful ceramics).

    In the mid-afternoon, we'll drive southeast through the “Crete Senesi,” a geological clay formation that prevents much growth and gives the land a barren, desert look. Our destination is Pienza, a beautiful Renaissance jewel overlooking the Orcia Valley. The town, originally called Corsignano, took its name after Pope Pius II, who was born here as Enea Silvio Piccolomini. The architect Rossellino planned the town following the example of the “Ideal City,” so loved by the Humanism culture. Along the way we'll stop at the charming medieval town of Bagno Vignoni, famous since Roman times for its thermal baths. Our hotel is an ancient 15th-century convent transformed into a Hotel Relais. (2–3 hours walking.)

  • Montalcino
    Day 5 : Montalcino

    We'll start with a morning transfer to the 13th-century abbey of Monte Oliveto Maggiore, one of the main Benedectine monasteries. Here we’ll admire the famous frescoes of Sodoma and Signorelli depicting the life of St. Benedict on the walls of the cloister. From the Abbey we'll walk to Chiusure and on to Buonconvento, from where we’ll drive to nearby Montalcino for a tasting of Brunello wine. Later we'll return to Pienza, where we'll enjoy dinner on our own. (3 hours hiking.)

  • Itu_day6_bgstk_perugia
    Day 6 : To Umbria – Lake Trasimeno

    We’ll begin this morning with a visit to the Piccolomini Palazzo, and before leaving Tuscany we’ll take a beautiful walk up to the little town of Monticchiello, facing Pienza. After lunch, we will move southeast toward Umbria, often called the “green and spiritual heart” of Italy. Its hilly, forested countryside exudes a slightly wild aspect, making it perfect for hikes among ancient farmhouses and abundant orchards, olive groves and fertile vineyards. Its soft, misty light is portrayed in the paintings of Raphael, who apprenticed here. Classic medieval hill towns crammed with artistic and architectural treasures rise up steep hillsides to reveal a historical past and provide an interesting counterfoil to our countryside rambles.

    A short transfer will take us to Castiglione del Lago, sitting on a promontory on the west side of Lake Trasimeno.The lake has been famous since Roman times: during his march on Rome in 217 b.c., the Carthaginian general Hannibal, accompanied by a large army and a number of elephants, defeated the Romans in the Battle of Trasimeno. The lake is now part of a regional park and shelters some rare species of birds. Our destination is Perugia, a splendid city of Etruscan origin also called “the pink city” for the color of its marble. We’ll enjoy a tasty fish dinner at a local restaurant. (3 hours hiking.)

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    Day 7 : Assisi – Spello

    In Umbria we’ll find the country’s mystical soul. The area is steeped in religion and is known as la terra dei santi, the “land of saints,” since it’s the homeland of St. Benedict and St. Francis of Assisi. We'll drive along the strada antica, the ancient pilgrimage road that, according to legend, St. Francis walked before meeting his death in Assisi. Upon arrival in Assisi, we’ll visit the Basilica Inferiore, the recently restored Superiore, and we will enjoythe beautiful Giotto frescoes. After a little more exploring in town, we’ll proceed to the Eremo delle Carceri at 2,300 feet, where St. Francis used to meditate and admire the beautiful views. Continuing up to the Rifugio Stazzi (4,000') we enter Subasio Regional Park and make a loop back to Assisi.

    On our way back to Perugia, we'll stop in Spello for an opportunity to taste several of the local wines, including the well-known blackberry-flavored Sagrantino. Spello has retained its Roman origins more than any other Umbrian city. The Portas (or entrances) of Venere, Urbica, and Consolare are the original entrance gates to the interior of this ancient city. After an optional walking tour of the town, we will return to Perugia for dinner on our own. (4 hours hiking).

  • Itu_day8_123_spoleto
    Day 8 : Bevagna – Montefalco – Spoleto

    We'll start with a transfer by van to the beautiful walled city of Bevagna. Here we’ll visit an old Cartiera, where paper is produced following ancient techniques. From Bevagna, we'll hike across fields and vineyards to the town of Montefalco, from where we can enjoy balcony views of Spello, Assisi, and in the far off distance, Perugia. While here we’ll also visit the Museum of the Convent of St. Francis, which holds the well-known fresco paintings of Benozzo Gozzoli. En route to Spoleto, we’ll stop at a Marfuga farmhouse (producer of olive oil) for an olive oil tasting. Tonight we overnight at Hotel Gattapone, located just in front of the spectacular Ponte delle Torri (bridge of towers) in Spoleto. (3 hours hiking.)

  • Itu_day9_123_carsulae
    Day 9 : l’Eremita

    After an early morning visit of Spoleto, we’ll drive 30 minutes to the village of Macerino, passing through what was once called Terre Arnolfe, the territory encompassing the towns of Terni, Cesi, Acquasparta, and Spoleto, which were once owned by Arnolfo, a Longobard duke. (The Longobards were a Germanic people who invaded Italy during the 5th century. They ruled Italy for more than 100 years and the Duchy of Spoleto was established by the Longobards in 571 AD.) From Macerino, we’ll hike through thick woods of chestnuts and oaks toward the l’Eremita complex, the place where St. Francis first wrote the sublime “Cantico delle Creature.” Here we will meet Brother Bernardino, who has restored the once-abandoned hermitage. From l’Eremita we descend to Poggio Azzuano, which overlooks the beautiful Roman ruins of Carsulae. (4 hours hiking.)

  • Day 10 : Departure

    After breakfast, we'll have a two hours transfer to the Florence airport for departures on homeward-bound flights. Upon request, we will also stop at the local railway station for travel to other parts of Italy or Europe.

Download Detailed Itinerary

DATES: Best time to go: June, September Departures: No group departures scheduled. Private departures are available on the dates of your choice, pending availablity. Call us for details.


2014 Prices
$4,995 (13 -16 members)
$5,395 (10-12 members)
$5,795 (6-9 members)

$1,000 single supplement

  • Hotel Villa Betania

    The Hotel Villa Betania is a small, family-managed hotel in a green park, only a 20-minute walk from the Ponte Vecchio Bridge in Florence. All rooms feature elegant parquet floors, air conditioning, and a satellite TV. Some rooms have stone walls and a terrace.
    Hotel Villa Betania has a new bar, and a terrace, where you can taste a selection of local wines. There is a smoking area on the terrace.
    The hotel is set from the traffic and noises of city center, and easily reached from Siena, San Gimignano, and the Chianti wine road.


  • Hotel San Lucchese
    San Lucchese

    In the hills of the Chianti wine district, this 15th-century villa is now a 4-star hotel with swimming pool, tennis court and Tuscan restaurant with terrace offering panoramic views. Rooms at the Villa San Lucchese are elegantly decorated and air conditioned. They come equipped with free Wi-Fi, a minibar and TV with satellite channels. Some also have a spa bathtub. The buffet breakfast includes homemade specialties and biological products. Guests can relax at the pool surrounded by the lush garden.


  • Hotel Il Chiostro di Pienza

    How many people can say they’ve stayed in a 15th-century convent? You can if you book Relais Chiostro di Pienza, a charming hotel set right in the heart of Pienza.  Set just 100 yards from Pienza’s cathedral, this historic hotel has its own well-kept gardens and a panoramic terrace offering lovely views of the Tuscan countryside. What could be better than a refreshing dip in Chiostro di Pienza’s outdoor pool after an afternoon exploring the old churches and monuments nearby? Sun loungers are provided on the lawn and you can get drinks and snacks from the bar. Relais Chiostro di Pienza’s rooms feature views of the old town, the Val d’Orcia countryside or the old convent itself. All come with tea and coffee-making facilities, minibars and satellite TV and some feature original ceiling frescoes. Free Wi-Fi internet access is available at reception.

  • Hotel Locanda della Posta

    Set in the center of Perugia along the main, pedestrian street of Corso Vannucci, Hotel Locanda Della Posta offers cozy accommodations in a historic building of the 18th century. At Locanda Della Posta you will be surrounded by shops, restaurants, monuments and museums. Stay in large, clean, bright rooms at Locanda Della Posta. You will find modern, cherry-wood furnishings and spacious bathrooms. From the large windows you can admire views of the city’s rooftops.Enjoy free Wi-Fi and affordable rates in this central hotel.

  • Hotel Gattapone

    At Hotel Gattapone you will enjoy exclusive views of Spoleto's medieval aqueduct and the beautiful valley below. The hotel has its own panoramic grounds, terrace and bar. The Rocca Albornoziana castle is just behind the Gattapone. The historic center of town is easily accessible from here. Gattapone Hotel is an old villa with modern rooms. All rooms have satellite TV and minibars. The staff is multilingual. Free Wi-Fi is available in the reading room.

Properties shown are representative of the accommodations we use on this trip, may not be inclusive of all accommodations we use, and are subject to change.

Expert leadership is the key to an exciting, unforgettable experience. Our trips feature gifted leaders for whom leading trips is a true vocation. Besides showing you wonders you’d never find on your own, they make sure everything runs smoothly and safely without a hitch. They are knowledgeable about all aspects of your trip, and take great pleasure in sharing their insights with you. More than just guides, they positively elevate your experience by being teachers, companions, and the best of friends. You’ll be in good hands with them every step of the way.

  • Silvia Giacon

    Silvia is an Italian, born and raised, who calls Venice her home. While she is an Architect by training, she has over 20 years of professional experience as a Trip Leader. Silvia lived in Toronto, Canada for over a decade, where she mastered her English language skills. Since then, she has led both walking and bicycle trips throughout Europe, and now guides are trips in Tuscany and Southern Italy.

photo credits: ©MTS Photo File


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Activity Ratings


Many activities are optional and involve fairly easy travel. Trips may include short hikes of two to three hours or optional walks at low elevations. Includes less demanding sea kayaking and river rafting trips with Class I-II rapids.


More active trips involving hiking over moderate terrain, usually - but not always - with vehicle support and at elevations less than 10,000 feet, or trips with long hiking days, multiple sea kayaking days, wilderness camping, or other invigorating activity. On many trips, you can elect to skip a day's activity, depending on logistics. Includes more demanding sea kayaking trips and river rafting trips with Class III rapids.


Hiking and trekking over steeper or more rugged terrain or where elevations may exceed 10,000 feet - often several days in a row. Includes more demanding sea kayaking trips (4-5 hours paddling a day) and river rafting trips with Class IV-V rapids.

Ultimate Challenge!

Our most demanding trips: trekking over steep, rugged terrain at high elevations (no vehicle support) or with substantial altitude gains and losses; trips to remote, extreme wilderness; mountaineering trips. Includes our most demanding sea kayaking (5-7 hours paddling a day) and river rafting trips with Class IV-V rapids.


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