Self-Guided
Tuscany Hiking Tour
Hiking in Italy is a visual, cultural, and culinary delight. On this walking holiday you spend four leisurely days rambling through central Tuscany at your own pace. A mix of quiet footpaths, medieval villages, and mouth-watering cuisine make for a perfect vacation. You do the hiking while we take care of the details. Every day we move your luggage from hotel to hotel. We provide daily maps, itineraries, and dining suggestions. On day three we schedule a winery tour and tasting. Explore the picturesque Tuscan hill towns of Panzano, Lamole, Volpaia, and Radda. Tuscany is known for its warm people, celebrated wines, and natural splendor. Come and see for yourself.
​Highlights
-
Chianti winery tour
-
The towns of Greve, Panzano, and Radda
-
Beautiful vistas of vineyards and olive groves
-
Peaceful country back roads and footpaths
-
The Lamole restaurant called Il Ristoro di Lamole
Price
US$ 800 per person, double occupancy
Dates
Any date, Mar 1 to Dec 1
Single Supplement
+ US$ 200 for single room occupancy
Length
5 Days, 4 Nights
Start / Finish
Greve / Radda in Chianti
Route Rating
Moderate: 3-10 miles (5-16 km) per day of hiking with some steep ascents/descents.
Terms and Conditions >
Daily Itinerary
Day 1: Greve in Chianti
The hiking tour begins in the town of Greve, 19 miles (30 km) south of Florence. Travel to Greve on your own (11 busses daily from Florence). Walk one hour to the tiny hamlet of Montefioralle, a walled castle on a ridge above Greve. For extra distance hike through an olive grove to the Romanesque church of San Cresci. Back in Greve be sure to visit the Enoteca Falorni, Chianti's largest wine shop. Even if you don't drink wine you can sample local olive oils, cheeses, and prosciutto.
​
Day 2: Panzano
Hike two hours through vineyards and olive groves to the medieval village of Panzano. Explore the remains of the town's castle or relax at the hotel pool. The Oltre il Giardino restaurant offers the best views in town. Dine under their wisteria pergola high above the Val di Conca. For something different head to the Solociccia restaurant where you can enjoy a six course feast offered by the town's charismatic butcher.
Day 3: Lamole
Follow a scenic ridge past vineyards and villas on your way to Lamole. Hike past a goat farm and spend the night in an 18th century stone farmhouse. Watch the sunset while dining at the Ristoro di Lamole restaurant. For more miles do an optional loop through the Mount Michele National Park.
​
Day 4 and 5: Radda in Chianti
A canopy of chestnut trees leads you to the stone hamlet of Volpaia. The 13th Century Volpaia castle has been transformed into a winery. Tour the winery and sample their full-bodied Chianti classico wines. Have lunch al fresco overlooking the village's central piazza. Your walking holiday ends in Radda in Chianti, a perfectly preserved medieval village. On day five depart Radda by bus or taxi. We will be happy to assist you with your travel planning.
Daily Distance
Lodging
Albergo del Chianti
Greve in Chianti (1 night)
Located in an 11th Century building on the main piazza of Greve, this family-run hotel has a salt-water pool, air- conditioning, and a restaurant.
hotel website >
La Pensione di Vignamaggio
Panzano (1 night)
Located on the main square, La Pensione di Vignamaggio has a beautiful garden and swimming pool with panoramic views over the Chianti hills.
hotel website >
Fattoria di Lamole
Lamole (1 night)
All the rooms have modern en suite bathrooms, terracotta floors and wood-beamed ceilings. You will fall asleep to silence and wake up to the sounds of the birds.
Hotel Palazzo San Niccolo
Radda in Chianti (1 night)
This four-star hotel is located in a 15th Century palace. The rooms feature wooden ceiling beams, terracotta floors, and marble bathrooms.
hotel website >
What's Included
-
All lodging
-
All breakfasts
-
Luggage transfer from hotel to hotel
-
Winery tour with wine tasting
-
Four beautiful hikes
-
Route notes and maps
Departure from Radda
End of Tour
You hiking tour will end in the town of Radda. There is no train station in Radda. You can depart by taxi or bus. Bus travel times are listed below:
Radda to Florence: 4 per day, 2.5 hour
Radda to Siena: 4 per day, 1 hour
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
Self-Guided Walks of Italy
Explore Tuscany at your own pace. We provide detailed route notes, luggage transfers, great accommodations, restaurant suggestions, and sightseeing notes. You choose the dates. We take care of the details.
Can I really start any date I want?
Yes! You can start your tour any day of the week, March 1 through December 1. We have complete flexibility with the starting dates.
Why Chianti?
The winemaking area between Florence and Siena is called Chianti. The area is known for is spectacular views, food, and wineries.