5 Days of Autumn inToscana
Are you struggling to pinpoint the perfect location for your European vacation this fall? It’s tough… Hot girl summer has ended, and it’s officially time to see if those jeans you wore before the warm weather began still fit. Look no further and consider taking this relaxing trip to the charming region of Tuscany.
Firenze – Cinigiano – Siena – Montalcino
This journey begins with two nights in the city of Florence. You’ll then head south to the countryside of Cinigiano while taking day trips to Siena and Montalcino.
The Tuscan region is large and with so many beautiful cities and towns to explore, one can easily spend over two weeks here alone. This fall itinerary is for someone looking to alleviate the stresses and anxieties of life with nature’s fresh air and experience gracious hospitality, flavorful wine and delicious, homemade Italian cuisine… all in just a few days.
There’s just something so great about sipping wine and shoving your face with bowls of pasta, am I right? Well, in the fall you can do just that while admiring the amber, crisp Tuscan foliage. Also, who could ever say no to to Italy? When it comes to vacationing, the country can pretty much do no wrong. Where else can you talk all week with your hands and say fun Italian words like ciao, buongiorno, mi scusi, and prego.
Before you start packing your bags, let’s discuss the weather and what to expect.
The Weather
Most people aren’t inclined to book a trip to Europe once temperatures drop. But I’m here to encourage you to GO FOR IT!
Italy’s fall season is from September 21st through December 21st. As the weeks pass, temperatures begin to drop and the hours of daylight diminish. October experiences highs of around 72°F and lows of 52°F. Expect temperatures to drop a few degrees more in November.
Unfortunately, November is one of the rainiest months in Italy. But, on the positive side, with the cooler weather and occasional rain comes cheaper accommodations and significantly less crowds. Trust me, I get it!… It sucks not being able swim in the hotel pool, but there is something extremely soothing about sitting poolside in comfy clothes drinking your wine and watching the sunset. Just be prepared; pack a rain jacket and an umbrella in case you experience showers.
Day 1-2: Florence
Ciao Italia! This itinerary commences in Tuscany’s capital city, Florence or Firenze, the home of Renaissance art and architecture.
Airport, Transportation, & Hotel
To get here, you’ll fly into Florence Airport, Pertola. We chose to stay at the moderately priced, Bernini Palace Hotel, located in an antique 15th century building. Its location is in the heart of Florence’s historic district and only steps away from main attractions.
To save money, opt for taking the train located just steps outside the airport to the city center. Without knowing almost any Italian, we were able to navigate to our hotel seamlessly. There is no need for a car in Florence as the city is on the smaller side and all main sites are walkable. Whether it’s your first, second, or third time visiting, I would not recommend staying longer than two nights.
WHAT TO DO:
Cathedral Duomo (Cathedral of Santa Maria del Fiore)
- One of the most fascinating and popular sites in Italy. Visit this UNESCO World Heritage Site to view the intricate details of this Gothic-style cathedral. Take a tour inside and climb the hundreds of stairs to the top of the Duomo to enjoy one of Florence’s best views.
Osteria All’antico Vinaio
- You must devour a panini at this legendary sandwich shop. This place will always have an extremely long line wrapped around the block all times of the day so don’t get HANGRY! Snag your spot in line and have a friend bring back a spritz to enjoy while you wait.
Uffizi Gallery
- This world famous museum located in Piazza della Signoria features outstanding artwork from the Middle Ages to the Modern period.
Galleria dell’Accademia
- This museum is best known for Michelangelo’s famous sculpture of David.
Ponte di Vecchio
- The city’s first bridge built over the Arno River in 1345. It’s the only surviving bridge in Florence, as all the others were destroyed by the fleeing Germans during World War II. Take a stroll along this bridge where you’ll find plenty of shops selling gold and silver jewelry.
Piazzale Michelangelo
- Cross the Arno River and climb the steps of the Terrace of the Piazzale Michelangelo which provides the best view of the city of Florence. You’ll find local venders and occasional live entertainment. It’s a great spot to bring a bottle of wine and enjoy the sunset. It can get very crowded so give yourself some extra time to find a seat along the steps!
Mercato Centrale
- Stop by this marketplace to enjoy a bustling food scene filled with vendors serving a variety of Italian dishes.
Day 3-5: Cinigiano, Siena, & Montalcino
You’ve had your fix of Florence and now it’s time to pack your bags and head to the countryside to see the real magic of Tuscany. You’ll definitely want to have a car for this part of the trip. The highways in Italy are pristine and traffic moves expeditiously. In fact, some of the best views you’ll see in Tuscany are along the road. Just watch out for speeding cameras. I learned about those when my Italian ticket came in the mail to our home in West Africa eight months after our most recent trip. They’ll find you anywhere!
Only a two hour drive south of Florence, located in the countryside of Cinigiano, sits the breathtaking, Castello di Vicarello. Ugh… the hotel of my dreams. You’ll feel like royalty at this exclusive, enchanting estate with views overlooking the rolling Tuscan hills.
Castello di Vicarello is a 12th century castle made up of 9 different suites, all uniquely and elaborately designed. The suite we booked was equipped with a foyer furnished with a daybed next to a wood-burning fireplace and large desk area. Behind a set of heavy wood doors was a spacious bedroom that easily fit a king sized bed, bureau and benches. And finally, the large rustic-style bathroom included a soaker tub and stone-arched shower. The windows gave stunning views of the property and beyond.
The restaurant at Castello di Vicarello offers an experience of home-style cuisine using freshly picked vegetables and herbs from the garden. The food is top notch and the staff is accommodating to any special needs or preferences. Eating dinner here every single night was a no-brainer for us.
The estate has two separate pools and offers many different experiences onsite. You can choose between wine tasting, cooking classes, hiking, or learning about grape or olive harvesting.
We chose to spend a large portion of our days onsite as the estate was so beautiful, we couldn’t get enough. The experiences offered at the hotel were pricey, so we opted for the hike. We were given a map and followed the trails around the property with views of the vineyards, olive garden, and a river.
Day Trip To Montalcino
Hop in your car and drive 45 minutes to the famous, medieval town of Montalcino, known for its exclusive red wine, the Brunello di Montalcino and the Rosso di Montalcino. The town is built upon a hilltop and overlooks a beautiful landscape of grapevines and olive trees.
WHAT TO DO:
Wine Tastings & Tours:
- The main reason you’ve traveled to this town is for the wine, so spend the day touring different Montalcino vineyards and sampling their production. Check out this list of wineries to visit:
Castiglion del Bosco Winery: Gorgeous, highly rated winery, known for their warm hospitality and well-informed tour guides.
Podere Le Ripi Montalcino – Sample 5 different wines produced on-site, while nibbling on small bites of cheese and a plate of lasagna. Cost: €40/pp
Podere Il Cocco: Small, family owned business that produces organic Montalcino wine. Tasting includes samples of 3 different wines. Cost: €25/pp
Fortezza di Montalcino
- This fortress was erected in the 1361 as the town’s military defense. It underwent major renovations in the 1930s and is now free for visitors to explore. You’ll enter into the courtyard and if you’re interested in climbing the upper-most ramparts, you’ll have to pay 4€/pp. The fortress offers a great viewpoint of the old town. Also located inside is a wine bar, Enoteca la Fortezza, that offers tastings.
Walk around Piazza del Popolo
- The historical center of Montalcino where you’ll find numerous cafés and restaurants.
Day Trip To Siena
Finish your trip exploring the historical city of Siena located an hour and half drive north. The city is located about 200km north of Rome and about 60km south of Florence. The old city of Siena is an outstanding destination with cobbled streets and tall medieval buildings that make you feel like you are living in a different time. It’s compact enough to explore its maze-like streets and see its highlights on foot in just a few hours.
WHAT TO DO:
The main reason tourists come to visit Siena is mainly to walk around the city to enjoy the ancient atmosphere and admire its charming beauty.
Top Attractions:
- Piazza Del Campo
- Palazzo Pubblico
- Torre del Mangia
- Piazza del Duomo – Siena Cathedral
Visit the famous, “shell-shaped,” medieval, public square known as Piazza del Campo. The side streets will lead to you a large open area, filled with brick buildings, restaurants, shops, and cafes. In the square you’ll look out to the Palazzo Pubblico, and sleek tower, Torre del Mangia. Palazzo Pubblico, the town hall, is now a museum which showcases local artwork. The tower offers incredible views of Siena if you’re up for climbing over 400 steps to the top.
Just a few minutes away is the stunning Piazza del Duomo – Siena Cathedral. Admire the intricate details and take a tour inside this medieval church. You’ll be able to see some of the works of Michelangelo, Bernini, and Donatello.
Siena overall is a wonderful place to walk around aimlessly and stop around local shops and restaurants to enjoy staple Italian dishes. No trip would be complete without a gelato break or two.
Now that you’ve read this guide, I hope you highly consider adding Tuscany to your bucket list! This place is something special and unlike anything in the world.
2 responses to “Italy: 5 Day Fall Tuscany Itinerary”
Lovely Itinerary! Love traveling during off peak time to avoid the crowd! Doubt my jeans will fit after a trip to Italy!
Wow! This is amazing. Alot of great information & such beautiful pictures. Happy for you & proud of you.
Blessings! Love you Jesssssssss!🥰