Self-Guided Montalcino Hiking Wineries and Castles

Price
US$ 1,150 per person
(Single Supplement)

Traveling alone?
Join a self-guided tour that has already been scheduled. We can’t run self-guided trips for one person, but we may have already booked a self-guided tour that works for you. More info

Group of three?
Tour prices are based on double room occupancy. Groups of three on self-guided trips have two options:
Option 1: Request a triple room. With a triple there is no single supplement. Option 2: Pay a single supplement (US$ 50/night) for the single room.

Dates
Any date from March 1 to October 31

6 Days, 5 Nights

Route Rating
Moderate to Challenging: 5-9 miles (8-15 km) per day of hiking with some steep ascents/descents.

Start / Finish
Montalcino / Montefollonico

Highlights

Thermal Baths, Bagno Vignoni
Ercolani Wine Cellars
Montalcino castle
Gregorian chants, Sant' Antimo
The town of Pienza
The hill town of Montepulciano

What's Included

All lodging
All breakfasts
Luggage transfer from hotel to hotel
Private shuttle on Day 2 to Sant'Antimo
5 beautiful hikes
Route notes and map
Use of cell phone for emergencies

Cancellations: Terms and Conditions

» Tour Summary
» Map and Distances
» Hotels
» Photos

Wineries and Castles

What if it rains?

If you prefer not to hike you can easily get to your next stop by public transport. Hourly trains connect Levanto and the five villages of the Cinque Terre. Frequent ferries run between Riomaggiore and Portovenere.

Why Self-Guided?
Explore Southern Tuscany at your own pace. We provide detailed route notes, a cell phone, luggage transfers, great accommodations, restaurant suggestions, and sightseeing notes. You choose the dates. We take care of the details.

Self-Guided Montalcino Hiking Wineries and Castles

These castles and wineries are open to the public at no charge.

Montalcino Castle, Montalcino
The 14th century Montalcino castle is right out of a fairy tale. You can see the ancient walls, towers, and the basilica. Inside the castle is a fabulous little wine shop with the best wines from the region. Climb the castle walls for great views.

Monticchiello Castle, Monticchiello
The castle of Monticchiello dates from 973. The castle was a major part of Siena’s southern defenses and consequently endured frequent attacks, destruction, and occupation. Today the Monticchiello maintains its formidable walls and medieval gate.

Ercolani Winery, Montepulciano
Tour the ageing cellars of the Ercolani winery. Dug into the earth these ancient cellars were originally used for grain storage. Today they house oak and chestnut wine barrels as well as a permanent exhibition of iron tools and instruments from Gothic and Renaissance times.