Planning to spend a few days in Montalcino? Read wedding planner and tour guide Serena's account of her holiday in Brunello town this summer. 

You never learn enough of Tuscany and whenever you have the chance to tour an area, you go back home with the feeling that yet something is missing and you need to go back to see more… This sensation was even stronger when visiting Montalcino and Val D’Orcia this summer with my family.

Montalcino, view towards Crete Senesi
View from Montalcino over the hills of the Crete Senesi and Val d'Orcia

I got in contact with Katja of Map It Out - Tuscany and she immediately introduced me to some of the best wineries and B&B's in Montalcino. Some friends of mine also joined us with their kids, so that the group increased in toddlers and in travel “requirements”…

Our tour lasted three days during which we spent two nights in Montalcino at B&B Porta Castellana and one in Bagno Vignoni at Locanda Il Loggiato.

Day 1
On the first day we arrived in Montalcino, where Dida, the owner of Porta Castellana, was waiting for us. The room she had reserved for us was very nice and spacious to welcome our family. She immediately made us feel at home and provided some tips for the evening and day after. The highlight of this place is the position and the parking (which is right in front of the B&B, a rarity in hilltop Montalcino). Just make sure you are okay with driving through a couple of narrow alleys. The B&B overlooks the Val d'Orcia stretching to Pienza and allows for a nice view onto Montalcino's medieval buildings. 

Our friends were staying outside the town, about 4 km from the center, in Agriturismo Villa a Tolli. This place is located at the end of a gravel road which runs in the woods for around 2 km, before reaching the old hamlet with a small church, surrounded by olive groves and vineyards. The beautiful scenery allows for a relaxing “out-of-time” stay. The apartments are rustic and authentic Tuscan country style. Breakfast was average ad the pool a bit too cold even for early August summer heat, but the possibility to sit in the courtyard and sip a glass of wine at sunset was priceless.

Montalcino vineyards, cypress trees and lavender from Villa Tolli
View from Villa a Tolli

In the afternoon, I had planned to meet with our guide Teresa, who was going to introduce us to the history and traditions of Montalcino (the tour was booked via Montalcino's tourist office). We had a walk along the main street, where I also run into Laura from the Palazzone winery - such a small town Montalcino, isn’t? But I’ll tell you later about her…

During our tour we heard about the independent attitude of people from Montalcino, who never had a manor to protect or guide them during the several sieges, nor did they ever surrender to the Florentine and Sienese people who craved their wealth. Montalcino in fact, thanks to its ideal position, controlled a wide area to the north and south and had direct access to fresh water springs, which allowed its citizens to survive at times when the town was under siege. During the Middle Ages Montalcino's buildings had windows only towards the interior part of the town in order to strengthen the town walls during possible attacks. Nowadays, with medieval warlords being a thing of the past, each shop lining up on the main street has windows or even balconies that open up onto a breathtaking panorama over the Val d'Orcia (a UNESCO world heritage site). 

I'd recommend a walking tour when stores are open. Like that you can have a peak here and there from the various shops in the town center. Apart of world-class wines you will also discover Montalcino's very tasty treats. Stop at Mariuccia’s for some tasting of pan pepato, freshly baked ricciarelli, panforte and the very local cioccolatoni (big chocolate fudge sweets). 

Sweets and chocolates at Montalcino's Mariuccia pastry shop

While strolling up and down the streets of Montalcino, we found out that archery is still a traditional sport here, dating back to medieval times. Each contrada (town district), has its own club, which offers street dinners in the weeks before the archery contest in mid August. Therefore, we headed to contrada Travaglio, which - according to our hostess Dida - serves the best food in town. We had a very nice dinner, including three courses for €15!

Travaglio alfresco dinner in Montalcino
Dining with the locals in downtown Montalcino

Before our local dinner, we enjoyed a spectacular aperitif in the Montalcino fortress wine bar, right inside the main tower. You can actually access the guard's walk and enjoy a breathtaking 360 degree view of Montalcino and its surrounding countryside (the Crete Senesi, the Val d’Orcia and the hills of the Maremma). You need to pay a ticket in case you don’t drink, but it is well worth paying and drinking in such an amazing spot!

Wine shop in Montalcino's fortress
Plenty of selection at the wine shop in Montalcino's fortress

Read on about day two and three of Serena's Tuscany summer tour on her Wishversilia blog

Serena is the owner of the Viareggio based Wishversilia travel agency. Whether you're looking for a beach holiday in the region's north, an excursion to Carrara's marble quarries or a helping hand with your wedding in Tuscany - Serena always has plenty of insightful suggestions ready. 

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