Italy Self Guided Walking / Tuscany
On our Tuscany Self guided Walking Tour you will follow timeless walking paths through the landscape that has inspired travelers for centuries. We offer this tour as a Self Guided Walking Tour, and it may also be chartered as a guided tour for groups.
Tour accommodations are in a splendid assortment of villas and charming country inns that will provide a sense of history and a taste of the local warmth and hospitality. You can look forward to gourmet meals that are characteristic of this region and made with the freshest local ingredients seasoned with tasty olive oil and herbs. You will be able to sample some of Italy’s most famous cheeses and wines from vineyards along our route.
This hiking vacation in Tuscany is more than just a great walk. It is your opportunity to fully experience the delightful countryside and wonderful people of Italy.
This self-guided tour is a fully organized vacation for the independent traveler who wants the freedom to walk at his or her own pace. You’ll have complete support behind the scenes. Our Italy representative will meet you at the beginning of your tour for an orientation. You will receive a packet with detailed route instructions, maps, suggestions for sights to visit along the route and emergency support phone numbers. You can take a spontaneous detour and always feel secure that your hotel room will be waiting for you. You will be able to travel at your own pace without a guide or support vehicle to hurry you along or to slow you down. Your luggage will be transported each day to the next accommodation, which will be reserved and prepaid. You don’t need to worry, as emergency support is just a phone call away.
2026 Price: €1420 Euros per person double occupancy
Price Includes:
- 7 nights hotel
- 7 breakfasts
- luggage transfers
- trip information package that includes maps, route descriptions, suggested sights to visit
- emergency phone numbers for our Italian staff support (shorter itineraries available)
Price Does Not Include:
International flights, lunches, dinners, beverages
Tour Difficulty
You choose your own dates and number of days and we organize the hotels, luggage transfers, route information and provide local support.
- Difficulty: Easy, travel at your own pace.
Tour Highlights
- Ancient walled cities
- Hillsides covered with olive trees
- Etruscan tombs and Renaissance art
- renowned wine regions
- Tuscany’s most interesting hill top towns
“The accommodations on our Tuscany Walking Tour were wonderful….all quiet and lovely. Wonderful breakfasts that fueled us until dinner! The itinerary suggested local dining spots which were all great, moderate, and again local and familial. We met many other independent hikers and bikers along the way that were doing similar trips.
As we have always organized our own trips, backpacking and kayaking, it was a real luxury to have our luggage moved from hotel to hotel. The bags always showed up and often were in our room. The local folks who do the transfers and drop offs were so friendly and real. Never treated us like anything but a friend with advise and tips about local happenings. The trek is so interesting with Etruscan history, beautiful vistas, friendly locals, incredibly fascinating villages, olive orchards, wine and great food. The itinerary really encompasses all that.”
Sample Itinerary
Day 1 – ARRIVAL TO CHIUSIS TRAIN STATION AND TRANSFER TO MONTEPULCIANO
Arrival in Chiusi where you are met by our Italian representative who will transfer your to Montepulciano and orient you to your tour. (The train takes about an hour and a half from Rome and trains operate every 2 hours throughout the day. See travel information below.) Hotel in Montepulicano, one of Tuscany’s highest hilltop towns. Renowned for its Vino Nobile, Montepulciano also boasts a unique blend of Renaissance architecture and is perched on a narrow ridge of volcanic rock.
Day 2 – MONTEPULCIANO/PIENZA (4 – 5 hrs walking time) – 15.4 km, Ascent: 430 meters, Descent: 502 meters
Today’s walk leads you to the western edge of Montepulciano (607 m), before descending through Porta al Prato to the splendid Church of San Biagio, where you join the red-and-white waymarks of the Siena Province Trail No. 6 towards Pienza. The route continues through farmland, then crosses the S146 and follows dirt tracks down into a quiet valley and up to the walled hilltop village of Monticchiello (544 m). From here, Pienza (491 m) comes into view on the next hill, and the final stretch crosses the Torrente Tresa valley before reaching your destination.
Stop at the walled village of Montichiello for lunch or a cappuccino before making your way to Pienza, a small town once called “the pearl of the Renaissance”. Partly redesigned by Pope Pius II, Pienza boasts a splendid Renaissance cathedral and the charming Palazzo Piccolomini. Sample pecorino, a local sheeps’ cheese.
Day 3 – PIENZA TO BAGNO VIGNONI (4 – 5 hrs walking time) 14.6 km, Ascent: 318 meters, Descent: 492 meters
The walking today crosses a beautiful region of rolling hills, oak woods and lovely villages. The Crete landscape is no doubt one of the most famous in the world; rolling hills in all the shades of brown or green; sturdy brick farm houses crowning the hilltops and cypress lined alleys design a perfect scenery that inspired painters since the Middle ages. Your destination tonight is Bagno Vignoni, a thermal spa town where the main square is a basin of steaming hot water. This is considered by many to be the most charming village in all of Tuscany! Hotel in Bagno Vignoni.
Day 4 – CASTELNUOVO DELL’ABATE – MONTALCINO (3 hrs walking time) 10 km , Ascent: 383 meters, Descent: 164 meters
You will receive a transfer in the morning (9am) to reach St Antimo Abbey (Castelnuovo dell’Abate) a lovely abbey isolated in the middle of a pastoral landscape. Enjoy the spectacular and evocative Abbey of Sant’Antimo. A nice walk to Montalcino, the capital of Brunello wine ; It is a nice medieval town with plenty of shopping possibilities well worth spending some leisurely time.
Day 5 – MONTALCINO – BUONCONVENTO – (4 – 5 hrs. walking time) 15 km , Ascent: 300 meters, Descent: 530 meters
Montalcino is renowned for its ruby-red Brunello wines, so you’ll spend much of the day strolling through vineyards as well as olive groves. Then you’ll enter the primeval landscape of the crete senesi , where shepherds tend the sheep whose milk is used to make pecorino cheese. Spend the next 2 nights at a delightful inn near Buonconvento.
Day 6 – MONTE OLIVETO – BUONCONVENTO (3 hrs. walking time ) 10.8 km , Ascent: 270 meters, Descent: 300 meters
Start the day with a transfer to Monte Oliveto Maggiore, a red brick construction in a rugged landscape. Visit the abbey before the tourist rush hours and start walking back toward your lodging.
Day 7 – GRANCIA DI CUNA – SIENA – (5 hrs walking time), 18.3 km, Ascent: 365 meters, Descent: 200 meters
Transfer in the morning from Buonconvento to Grancia di Cuna and then walk to Siena. Siena is our last stop. Savor a delicious ice-cream sitting at a Cafe on the edge of the Piazza del Campo where the famous Palio is run twice in a year. Stroll the small “vicoli” and cobbled streets, admire the purity of the Duomo architecture and taste some of the best Italian wines at the Enoteca Nazionale before leaving to your next destination.
Day 8 – DEPARTURE
Your tour ends after breakfast, but you will want to enjoy the sights of Siena before your departure. Stroll through Piazza del Campo and to the spectacular Duomo, one of the few full Gothic cathedrals built south of the Alps. There are both train and bus stations in Siena with easy access to both Rome and Florence. You might also choose to spend an additional day in Siena as there is so much to see here.