Day Trips from Florence: Off the Beaten Path in Italy

Tuscany has been inhabited for millennia, farmed and occupied and traversed, it’s a well worn yet endlessly enchanting landscape. It is named for an ancient, mysterious civilization, traces of which remain threaded through Roman, Renaissance and contemporary life – an Etruscan well high on a hill, Etruscan pottery shards connecting the modern ceramicist to an ancient local tradition. Everything has been written about Tuscany – and yet every visit feels brand new, a chance to discover another layer, another small town or cosmopolitan city , the gentle curve of the road revealing a glorious view, inviting a visit to any number of villages and towns scattered across this region, making the area perfect for day trips from Florence.

Tuscany Day trips in Italy

The hills and valleys change month by month – in May, bright fresh green grasses wave gently on the breeze, welcoming hillsides full of bright red poppies bobbing their heads. By July, yellow sunflowers turn their faces to the sky. In September, supple hills are revealed to be already-turned dirt, waiting for the fallow winter, readying again for the spring planting, while vineyards are just coming to the critical point of harvest. There is no better way to enjoy the myriad wonders of the region than leisurely dalliances amongst hill towns, quiet days exploring villages and evenings enjoying the cuisine and wine.

Tuscany can seem small when looking at a map, but the sheer depth of experiences means that you could easily spend oceans of time there. Picking an itinerary is both the most fun, and the hardest, part of the trip – inevitably, you will realize that you just can’t do it all when you are making day trips from Florence. As I like to say – that just means you’ll have to come back!


In the area around Florence, and more specifically if you want to make Montepulciano with kids your home base, there are dozens of day trips from Florence options within a few hours drive. Most of the villages are great for day trips from Florence with kids: medieval city centers are car free (or very car limited), elderly villagers smile at the kids, restaurant owners are happy to accommodate, and gelateria abound. We had the pleasure of visiting a handful of these over the last year; here’s our absolutely not comprehensive list of delightful dalliances!

Day Trips from Florence

Bagno Vignoni

A tiny hamlet in the center of the incomparably beautiful UNESCO heritage Orcia Valley, Bagno Vignoni is accessed by a small road that offers ridiculously gorgeous views of Monticchiello, if you arrive via one direction, and Pienza, via another. The village itself is barely a smudge – population 30, according to the 2001 census. However, it has a huge historical footprint: the Etruscans enjoyed bathing in the local hot springs, Romans consecrated the springs to the Nymphs, and by the 12th century, it was a significant tourist destination for christian pilgrims heading to Rome. Today, tourist from italy, germany and beyond visit the village to take advantage of the numerous springs, taking the healing waters by day and enjoying isolated silence by night.

The village is centered on the “Square of Sources” – Piazza delle Sorgente. Unlike most piazzas in Italy, this one is a pool – a hot spring, at the center of town. Unfortunately closed to the public, the steam rising from the water creates a sensational setting and an unusual focal point. The pool is surrounded by small stone buildings, a church on the west edge; cheerful geraniums and tiled roofs reflect in the still waters. A loggia on the south edge was once the public access point; it’s a delight to imagine pilgrims, walking thousands of miles on treacherous roads, pausing here for restoration. Today, the hills surrounding the town are full of spa hotels, offering all manner of refined services, day packages and retreats.

Immediately south of the village and the public parking lot lies the Parco di Mulini: the park of mills. This is an archeological site, with evidence of a medieval mill house and bathing rooms that can be partially accessed via walkways and interpretive signs. the hot springs continue to bubble, and they have carved paths in the stones: it’s not uncommon to find people sitting with their feet in the waters, reading books, picnicking, and enjoying the view.

The view itself is a marvel – the parco is set on the edge of a cliff, and besides the glory of the hills to the west, the turquoise spring waters themselves cascade down hundreds of meters to feed pools below. The pools are family friendly and also clothing options – beware, should you decide to explore further!

Day Trips from Florence to Montalcino Italy


West of Pienza, Montalcino was once a fortified town that developed a respected leather trade during the Middle Ages. The town is surrounded by defensive walls, built in the 13th century, with an imposing fortress at the southern edge of the walls. Perched high above the Orcia Valley, it holds commanding views across silvery olive groves and lush vineyards. Ruled by Florence from the Renaissance until the mid 19th century, the community gradually went into economic decline, losing population to the more vibrant cities to the north. However, wines made in the region, known as Brunelo di Montalcino, had already made their appearance and were particularly noted for their superiority – and rarity.

Prior to  the late 1940s, there was only one commercial producer noted in government documents, which had only 4 registered vintages: 1888, 1891, 1925 and 1945. In the post-war years, a small collection of vintners banded together to create standards for wines that would earn the Brunello label – and subsequently developed one of the more successful varieties on the market today. Only 50 years later, there are more than 200 designated producers, creating over 330,000 cases a year – many of which are featured in tasting rooms and cafes across the village.

Montalcino is an excellent destination for gastronomically aligned parents traveling with princess-crazed, castle loving children who have decided to vacation in Florence. Walking up from any of the public parking areas arrayed around the base of the town, the small streets are easily maneuverable with a stroller or on foot. The easy-going pace invites casual wanderings, and the array of cafes, trattorie and gelaterie provide plenty of places to refresh. The fortress could offer hours of adventurous daydreaming and playtime.

Day Trips from Florence to Buonconvento


Located just a few miles north of Montalcino, and an easy day trip from Florence, in the heart of the Orcia Valley, Buonconvento is another car-free walled city, but blessedly free of hills, should you tire of pushing strollers up and down!

The local museum has a number of pieces by Medieval and Renaissance Tuscan artists, whose legacy questionably lives on in the art festival held just outside the old walls on weekends. The village gathers outside of the Bar Sport at the center of town for important futbol matches, and Osteria Vineria La Porta di Sotto offers phenomenal regional specialties for lunch and dinner, as well as a terrace perfect for people watching. Even in the height of season, Buonconvento is mostly touristed by Italians, though menus are also in english.

Day Trips from Florence to Siena Italy in Tuscany


Siena merits its own visit when you are planning your day trips from Florence, especially during its famous medieval festival, the Palio. A 90 second horse race, 3 laps around the main campo, the Palio takes place July 2 and August 15th, but its energy can be felt year round, from horse blessings in the cathedral to drummers practicing their staccato precision up echoing stone streets. Siena was an extremely powerful medieval city, rivaling Florence for centuries, and has the art, architecture and attitude to prove it. Siena is also the home of Banca Monte dei Paschi di Siena, the world’s oldest, continuously operating bank. Civic pride is very strong, and despite the hordes of tourists that have discovered this amazing town, the locals remain marvelously generous and present.

After years of visits daydreaming that I knew a local, I finally met a native Sienese in a cafe in Chicago, of all places! We exchanged emails, and in September, Michele took us on a wonderful tour of his neighborhood: the Contrada di Selva. Like most medieval tuscan villages, Siena is divided into 17 different wards, or contrade – each has its own flag, colors and pride. I had cheered the winning Selva horse during the 2003 Palio, and her flag remains on my walls. I was thrilled to get a deeper look into one neighborhood!

La Selva is immediately west of the Siena Cathedral, with narrow cobbled streets lined with buildings standing 3 – 5 stories tall. We happened to visit just after their most recent victory and learned that the winning contrada has the honor of hanging their flags and celebratory lighting until the following race, creating a marvelously festive scene. Palio stories run deep: we passed through a series of arches and arrived at a wooden door with a brass horse-shaped door knocker: the palio stable, where the racing horse is housed (right in the center of town!) They used to station sentries to prevent any harassment of the race horses, until they realized it would be easier to just house the jockey and the handler right next door – and so it goes, hundreds of years later.

Just beyond is the Piazetta della Selva – a small piazza, mostly a parking area, with a church on one side and a petite fenced-off fountain at the other featuring a rhino – the icon of the neighborhood. “This is the center of the Selva universe,” said Michele. “Even before the church gets to baptise our babies, they are baptised to la selva.” The community center is just behind us – “Here, they host community dinners, weeknight meetings; there is a ballroom, some sports rooms.” Walking with him through the quiet streets, smiling as he says “hello” to everyone – Stefano on the ladder, changing the lights; Andrea at the door to the pottery shop – you get the feeling that this is a truly proud, delighted and perfect small town.

Montepulciano with kids

Know Before You Go

  • Check for the best rates and availability on Tuscany hotels and hotels in Florence
  • Parking lots are usually found at the outer edges of the medieval areas. pay the rates accordingly.
  • Eat at the best places when you plan your day trips from Florence. Have a lingering lunch – the kids can run around, within reason, and you can enjoy a long, leisurely meal. 

Where to eat in Tuscany


Day Trips from Florence

Bagno Vignoni, Montalcino, Buonconvento, Cortona vertical, Tuscany landscape and Siena via

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