It's no secret that the scenery in Tuscany is some of the best in the world. The gently rolling hills are covered in fields and vineyards, dotted with stone villages and tall Italian cypress trees. While staying in Florence, it's more than worth your while to take a few days out in the countryside, exploring medieval cities and cooking in wine country. Of course Tuscany is beautiful in the summer, but I couldn't help thinking that it would feel even more magical - and a bit less busy - in autumn.
Just over an hour south of Florence lies one of my favorite cities, Siena. It's also one of the most visited spots in Tuscany, so I'm not alone in my fondness for this place. While you can - and should - spend at least a day in Siena, the best times are in the morning and evening, when all the day trippers and tour buses are gone. Plan to stay a night or two somewhere like this if you have the time.
Siena's beautiful striped marble Duomo has a bell tower that rises above the medieval rooftops from the top of the hill. The church itself is incredibly intricate, from the sculptures on the facade to the stars painted in the dome and the stripes of dark green marble inside and out. Unlike some other duomos in Italy, there is an entrance fee, and the opening hours are pretty limited.
The broad, scallop-shaped Piazza del Campo is the heart of the city and home to Siena's other tall tower at the Palazzo Pubblico. Lined with restaurants, the square is a perfect place for an afternoon spritz and some great people watching. If you're in town during July and August, don't miss the famous Palio di Siena horse races!
In the evening, wander through the seventeen districts of the city and find as many hidden alleyways as possible - Vicolo delle Carrozze and Vicolo degli Orefici are possibly the most charming streets in Siena. Walk up along the city's 16th century fortress for the best views of the city and the countryside. Finally, settle in for a long dinner at La Sosta di Violante or Taverna di San Giuseppe.
This medieval town between Florence and Siena is known for its skyline of tall stone towers, which earned it a spot as a UNESCO World Heritage Site in 1990. San Gimignano's second claim to fame is the local Gelateria Dondoli, winner of the gelato world championship. Though it's a small hilltop city, you can easily spend an entire day in San Gimignano and not be bored in the least.
The charming streets that run up and down the hill are lined with shops and restaurants offering local crafts and foods - from specialties like ceramics and wild boar sausage to some of Tuscany's best leather goods and white wines. Be sure to wander off of the main roads, through the medieval archways, and into the tucked-away alleys and little neighborhoods. Stop in at Caffè Giardino for a cappuccino break.
If you're in town on a Thursday morning, you can shop the weekly market that covers the triangle-shaped town center, Piazza della Cisterna. The beautiful cistern in the middle of the square was the the town's water source for centuries, but the main attraction today is Gelateria Dondoli and its award-winning gelato. Don't shy away from the long line; it moves quickly, and you'll have a good view of the piazza while you wait. The steps outside the nearby Duomo are a perfect place to sit and enjoy your gelato before heading inside to see the church's wonderfully preserved frescoes.
Later, walk along the city wall for some of the best views over the surrounding vineyards and olive groves, out into the countryside. You can even find the medieval font, an ancient water source for the city. For dinner, try Osteria del Carcere, find the makings of picnic at La Buca di Montauto, or have some truly Tuscan pizza at Il Trovatore.
When you're looking for a day trip that's completely planned for you, I can't recommend this one enough. Early one morning, our small group - just four people total - met in the center of Florence and drove out into the hills of the nearby Chianti region. Our first stop was at a small family-run organic vineyard, where we learned all about the winemaking process and regulations in Tuscany during our visit.
After a bit more driving through Chianti, we arrived at a hilltop villa where we spent the next few hours in the kitchen with our wonderful chef Alessio. With a lot of careful guidance, we made our own pappardelle and ravioli, two sauces, and tiramisu - with plenty of local wine around to inspire our cooking. It was an enormous, incredible meal when our little group sat down to eat in the villa's dining room. Before the drive back to Florence, we nearly cleared out their shop of speciality oils and seasonings.