After a day exploring Siena’s main sights, indulge in a lazy morning at your hotel, hopefully with a back garden as beautiful as that of Il Giardino di Pantaneto.
A healthy breakfast with Tuscan views is hard to beat.
Take a morning stroll in the empty streets in search of the city’s many historic icons.
Fountains are a defining characteristic of Siena and you’ll see many on your walks. As a hilltop town with no river running through it, the population had to work hard to bring water to the city center centuries ago. Some are monumental like Fontebranda, the oldest, with gothic arches and lion head spouts.
Three large basins served various purposes: the fresh spring water would flow into the first which was for drinking, the next was for the animals, and the third for washing clothes.
Just up the street from Fontebranda, you’ll find the Sanctuary of Saint Catherine, the patron saint of Italy. She was born and raised right next to the famous medieval fountain. Her birthplace was turned into a shrine you can visit for a few minutes with a lovely portico, a small church and various artworks.
And just around the corner from the shrine is one of the best viewpoints in Siena. Get to the beginning of Via Camporegio with the Cathedral of St. Catherine in front of you and a staircase leading down to Fontebranda and walk up to the right where there’s a restaurant.
This is what you’ll see – a horizontal cityscape of Siena with its two medieval masterpieces on each end, the Duomo and Torre del Mangia in Piazza del Campo. I came back to this viewpoint multiple times to see it in different lights and it was always magnificent.
Taste the Chianti
The vine-clad hills of the Chianti Classico wine region stretch between Florence and Siena with many vineyards only a few minutes outside of the city. It’s an easy and wonderful addition to your day, whether you have your own transport or opt for one of the many tours available.
Within 10 minutes of leaving Siena you’re surrounded by hilly vineyards and olive groves as far as the eyes can see.
My Tuk Tuk tour was a blast – the open air drive on winding roads with wine tasting is possibly the best 3 hours to break your day in Siena.
We stopped at the gorgeous and modern Vallepicciola wine estate for our tasting.
I like good design and architecture almost as much as I love wine (!) so this place was a hit.
We started with a sparkling Chardonnay (refreshing after the sunny drive) followed by a Grand Cru and a Chianti Classico Reserve DOCG, both 100% Sangiovese and sublime. Growing up with only the ubiquitous Chianti bottle in a straw basket (fiasco), I knew little about the region’s wine production and learned a lot. Regular Chianti is made in much of Tuscany but when you see the term ‘Classico’, it means it was made exclusively within the defined Chianti area where I was and with at least 80% Sangiovese grapes.
The drive back into town is just as dreamy, basically a succession of wine country postcards.
Siena deep dive
It’s only midday, you’ve had your morning wine and fresh country air… which means you’re in the perfect mood to soak up all the little jewels of Siena you missed yesterday. The center has a lot more to offer, including a great antiques market in the Market Square (behind the Palazzo Publico).
Browse the stalls for old prints, rare coins and vintage jewelry for unique souvenirs.
Surely ravenous from your morning adventure, you’re lucky that one of the most scenic lunch spots in all of the city is right there – Locanda dell’Oste. The panoramic views from the terrace overlooking the surrounding hills and community garden are the first draw but the food deserves praise too.
A kale flan, seasonal roasted vegetables and orange-glazed duck really hit the spot.
For the rest of the afternoon, your only plan is to slowly explore Siena’s neighborhoods and spot its fantastical creatures. The city is divided into 17 historic districts, called contrada, each with own church, museum, boundaries, civic identity… and totem animal.
You can tell which neighborhood you’re in just by the creature featured on its buildings. The only exception is the Tower neighborhood whose symbol is an elephant carrying a castle tower on its back. It’s a lovely and quiet part of the city with beautiful views over the valley.
Antique iron rings still line the stone walls, historically used to tie up horses and other working animals.
Let your exploration lead you ever further away from the historic core – it’s small so it really means 10 min max in any one direction. You’ll find quaint leafy piazzas, gothic churches and little cafes everywhere. I loved getting lost in the Giraffe district (when else are you going to say this?).
Besides animals, you might also find seductive women staring at you from above. Siena has a few unique wall sculptures, notably the Donna alla Finestra (Woman at the Window) in the Caterpillar neighborhood.
While you’re looking up, admire the colorful street lamps also marking the districts.
But of all the structures, I think trying to locate all 17 water fountains with their animals is probably one of the best scavenger hunt you can do. From monumental Fontana del Leocorno (unicorn) made of rare yellow marble only found in the area, …
…Selva (Forest or tree – somehow a real tree growing at the back of a rhino?) and Pantera…
…to aquatic Tortuca (turtle) and Onda (wave), your search will bring you to some of the prettiest corners of the city.
End the afternoon with some window shopping along Via di Città, a curving street that hugs the Piazza del Campo.
There are a few souvenir shops though you’ll find the best kind of gifts in the old art and food stores, like at Antica Drogheria Manganelli. The pharmacy-style glass containers filled with candies and loose teas are worth photographing, and the walls lined with panforte, mints and pasta bags in all shapes and colors will have you reconfigure your suitcase priorities.
Art is not limited to historical references – you’ll also find modern galleries and gorgeous ceramic workshops showcasing Siena’s contemporary flavour.
Stop by Caffè Fiorella, a bar/roastery with delicious espressos and tempting pastries, or Gelateria Nice for your pm treat.
Dinner time is especially magical around the piazza with small outdoor terraces illuminating the narrow hilly streets.
Before choosing where you’ll have your last meal, make sure you stop by this morning’s viewpoint on Via Camporegio one last time. As beautiful as it was in the morning light, is it simply stunning at sunset.
End the day sitting on the terrace of Hostaria di Pantaneto 55 surrounded by the old city walls and the aromas of the hearty cuisine coming from the open kitchen. Fried polenta with porcini and Sienese-Style Osso Buco are as good a Tuscan dinner as there will ever be…
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