Ah, Tuscany! Here, in the heart of Italy, medieval villages bask in the warm evening sun. Grapes and olives burst from hillside vineyards and ancient olive groves. Minestrone stews in the pot and you can smell the fresh basil and oregano from the garden. Some of the world's finest artwork is on display in small museums and country churches. Explore this birthplace of the Renaissance as we hike the Tuscan countryside and visit some of the region's premier art destinations, all the while savoring the best in Italian food and wine. Along the way, we'll introduce you to the warm hospitality and friendly people that make Tuscany Italy's premier hiking destination. Our tour begins with two nights in Greve in Chianti in the heart of Tuscany's world famous Chianti wine region.
Day 1: Tour begins in Greve in Chianti, Italy
Highlights: Meet in Greve in ChiantiWe'll meet you in Greve in Chianti today. Greve is the heart of the famous Chianti wine region. Surrounded by olive and vine clad hills the region forms the core of the typical Tuscan landscape dating to the 16th and 17th centuries. We will lead an orientation walk this afternoon before a glass of wine and dinner together in a local trattoria.
Day 2: Greve in Chianti
Highlights: Greve in Chianti, Etruscan roads and the Castle of UzzanoOur hike today takes us from the main square of Greve into the heart of Chianti Classico. Greve originated as an Etruscan settlement 600 BC. There was a castle here in Medieval times but now only remnants of the walls recall that historic time. Our destination is the castle of Uzzano, surrounded by woods and vineyards. A part of our hike follows the ancient Etruscan road that connected Volterra to Fiesole. Enjoy a picnic lunch along the way. We'll taste the famous Chianti wines together this evening before dinner on your own. Mileage: 4-5 hours (about 12 km.; 7.5 miles)
Day 3: Hike through the Chianti hills from Castellina in Chianti
Highlights: Castellina in Chianti and the towers of San GimignanoWe leave Greve in Chianti this morning and shuttle to nearby Castellina in Chianti. Our hike begins here and takes us south and west to the village of Lilliano and on to the Rocca delle Macie for a visit of the vineyards. We'll find a nice spot for our picnic lunch and then shuttle on to our hotel in San Gimignano. Famous for its medieval towers, San Gimignano enjoys the reputation as one of the best-preserved 14th century villages in Europe. Our hotel is in the village. Have a rest, explore on your own, and enjoy a coffee in the square. We have dinner together this evening. Mileage: 3 hours (about 9 km.; 6 miles)
Day 4: Explore San Gimignano
Highlights: Charming San Gimignano, optional hike in the hills of TuscanyToday is a free day to explore San Gimignano, so feel free to sleep in or join us for a half day hike into the nearby hills. San Gimignano, one of Tuscany's most visited towns, is indeed the quintessential Tuscan village, famous for its medieval towers and narrow cobblestone streets. You can choose to spend the whole day in town or take a short hike into the hills and surrounding villages before wandering around the streets of San Gimignano. We'll suggest some of our favorite trattorias for dinner on your own tonight (and don't forget to save room for gelato!) Mileage: 2-3 hours, 8 km (5 miles) on varied terrain.
Day 5: Hike San Gimignano to Volterra
Highlights: San Gimignano, Volterra and ruins of CastelvecchioWe continue west today to Volterra, one of Italy's most famous Etruscan towns. It is a long but interesting hike through the ruins of Castelvecchio and the borgo (hamlet) of Pignano. We'll take picnic supplies with us and find the perfect spot along the way for our lunch. Views of the Etruscan town of Volterra, set high above the surrounding landscape, dominate the end of our hike today. Volterra was one of the nine most important Etruscan cities in the pre-Roman era; we'll be here two nights so you can get to know this still undiscovered town in Tuscany. Dinner is together tonight. Mileage: 6-7 hours; 17 km (11 miles) on mostly flat terrain.
Day 6: Loop hike around Volterra
Highlights: Hike along the Via Salaiola - the ancient salt route, Volterra's famous alabaster workshopsWe'll do a loop hike around Volterra today, starting along the ancient Via Salaiola -- which once connected the salt mines of Volterra with the Etruscan town of Fiesole near Florence. Our trail passes by small hamlets, vineyards, chestnut groves and raspberry bushes before arriving at two Etruscan tombs we can visit. We'll be back in Volterra this afternoon so you can visit the city, its Etruscan ruins and museum and the many alabaster workshops that dot the town. Dinner on your own this evening. Mileage: 4-5 hours, 12 km (7.5 miles) on varied terrain.
Day 7: Siena
Highlights: Renaissance SienaWe shuttle to a village near Siena today to end our hiking tour with a hike into Siena. This way we enjoy views framed by olive groves and cypress tress as we hike towards this wonderful Renaissance city. We pass through few villages today as we follow trails and donkey paths that farmers going to market would have used until the middle of the 20th century. Plan to be in Siena by mid-afternoon so you can enjoy a walk in this jewell of Medieval and Renaissance city planning. Our farewell dinner is tonight. Mileage: 3 hours; 9 km (5 miles) on mostly flat terrain.
Day 8: Tour ends in Siena
Highlights:You are on your own today after breakfast together. Siena is certainly worth another day if you have the time. From here trains take you easily south to Rome or north to Florence. We hope to see you again soon for another walking tour in Italy or another of our destinations.
HighlightsGreve in Chianti, Volterra , Wine tasting, Siena, San Gimignano
Includes"The Usual" plus... 8 days, 7 nights accommodation, 4 dinners with wine, & 7 breakfasts
Begin/EndGreve in Chianti/Siena
Arrive/DepartMilan, Rome, Florence, or Pisa
Daily Distance2-6 hours, 8-17 km (5-11 miles)
What to ExpectHikes on country roads and trails with some longer days and some town walks. Varied terrain, including some hills.
Please call 1-800-685-4565 or e-mail us for the dates for this tour.
Click on the "pins" for details about each day's highlights.
City (on route)
City (not part of route, provided for reference)
Thank you for your attention to detail, for the variety of experiences, and the warmth and professionalism of your tour guides. This was a beautiful initiation to the Tuscan countryside.
The food was outstanding and the guides were so informative about ingredients, preperation, customs, and regional specialties. They all had lots of enthusiasm and expertise. I drool just thinking about the dining experiences.