San Quirico d’Orcia is a small hilltop town in Val d’Orcia, one of the most scenic stretches of Tuscany. We first visited in late September, during harvest season, while staying at a nearby villa. We fit it in between stops at Pienza and Montalcino, not expecting much from a town this size, and left having […]
Planning a trip to Tuscany? This guide covers everything you need to build the perfect itinerary, whether you have 3 days, 5 days, or a full week. How long should you spend here? Where should you stay? Should you rent a car? What towns are worth visiting? These are all questions that may be running […]
Monteriggioni looks almost too perfect to be real. Perched on a rounded hilltop in the Chianti countryside, its ring of medieval walls and 14 towers appears almost exactly as it did in the 13th century, a complete, intact fortification unlike almost anything else in Tuscany. We visited on a day trip from Siena, just a […]
From world-famous cities like Florence and Siena to quiet hill towns and scenic drives through vineyard-covered hills, Tuscany offers a wide range of experiences, but deciding what to do (and what to skip) can be overwhelming. We’ve explored Tuscany on two very different trips: a one-week highlights tour with our kids and a longer 10-day […]
Some cities in Italy overwhelm you with options. Siena does the opposite, and that’s exactly what we loved about it. The historic center is compact and entirely walkable, the main sights are clustered within easy reach of each other, and the city has a pace that makes it easy to slow down. The things to […]
Pisa and Lucca are two popular day trip destinations from Florence. Their close proximity to one another, small sizes, and handy train stations make them very easy to combine into one amazing day trip from Florence. We’ve visited both cities on separate trips to Italy. We stopped in Pisa while traveling by train from Florence […]
Lucca is one of Tuscany’s most rewarding cities to visit. While Florence gets the crowds and Pisa gets the selfies, Lucca has a charm that’s entirely its own: Renaissance city walls you can walk or bike, medieval towers rising above the rooftops, and a piazza built inside a Roman amphitheater. What we loved most was […]
After two trips through Tuscany, we’ve visited a lot of hill towns, including Siena, Cortona, Montepulciano, Pienza, and a handful of smaller villages tucked into the countryside. Arezzo was one of the last ones we visited, and arriving on a Sunday in early October, we weren’t sure what to expect. What we found was one […]
The first time we visited the Siena Cathedral, it was a hot July afternoon and our kids, then 9 and 11, were well past the point of cathedral fatigue after several days of museums and churches. We weren’t expecting this to be the stop that won them over. But inside, with the mosaic floor on […]
Volterra, Italy is one of the most rewarding Tuscan hill towns to visit and one of the most underrated. We climbed the tower of Palazzo dei Priori for a 360° view of the countryside, walked a Roman theater that dates back to the 1st century AD, climbed Torre del Maschio with a guide and just […]
There’s a moment when you round a corner on one of Cortona’s side streets and the whole Val di Chiana valley opens up below you, and you think: how is this town not more famous? Tim and I had that moment during what was supposed to be a quick afternoon stopover between Arezzo and Assisi. […]
Perched on a hilltop in Tuscany’s Val d’Orcia, Montalcino is one of Italy’s most beautiful wine towns, famous for its Brunello wine, sweeping vineyard views, and charming medieval streets. Whether you’re here for a quick stop or a slow afternoon of wine tasting, this small town delivers one of the most memorable experiences in Tuscany. […]
Planning your list of things to do in Montepulciano? This hilltop town in southern Tuscany is one of the most atmospheric places in the region, known for its Renaissance architecture, sweeping views over the Val d’Orcia, and its famous Vino Nobile wine. Perched on a hilltop in Val d’Orcia, Montepulciano is compact but packed with […]
Pienza is one of those Tuscan towns that earns its reputation. Perched above the Val d’Orcia, this tiny UNESCO World Heritage Site was redesigned in the 15th century by Pope Pius II as his vision of the ideal Renaissance city. Walking its perfectly proportioned streets, it’s hard to argue with his ambition. We’ve visited Pienza […]
Siena rewards everyone who visits, whether you have one day in Siena or five. We know, because we’ve done both. Our first trip was a full five nights. We used Siena as our base for exploring the Tuscan hill towns, and most evenings ended the same way: the four of us heading down to Piazza […]
Traveling from Florence to the Cinque Terre? Here’s how to stop in Pisa to see and climb the Leaning Tower in just a couple of hours, without derailing your travel day. If you’re traveling between Florence and the Cinque Terre, Pisa is one of the easiest and most worthwhile stops you can add to your […]
San Gimignano is famous for its medieval towers, and yes, you should climb one. But a great visit here goes beyond the main piazzas and the gelato line at Dondoli. On our first trip, we arrived by bus from Siena on a busy morning with our kids, climbed to the top of Torre Grossa, ate […]