(Coming Soon) Val d’Orcia: Tuscany and a Taste of Florence

Fly into Florence, arriving at Amerigo Vespucci Airport for the most convenient experience, as it is about 20 minutes away from the city center. Sometimes, it may be more cost and/or time effective to fly to Rome or Bologna, then catch a fast train to Florence.

A car will be waiting for you to take you to your accommodations from Amerigo Vespucci Airport. Get settled in to your room for the night, but don’t unpack as it is just for tonight.

Today will be some attractions that are pretty close together, within a mile or two (2-3 km).

You are sure to be hungry, so head to the Central Market. This bustling food market is a hub for culinary delights, offering a wide variety of fresh produce, meats, cheeses, and prepared foods. Within the Mercato Centrale, there’s also a food court area where visitors can sample a diverse range of traditional Tuscan dishes and gourmet delights.

On your way to Piazza della Signoria, take a walk by the Duomo, the building with the largest dome in the world. This gives perspective to the rest of the city, providing a landmark as reference.

Piazza della Signoria is essentially an outdoor museum with a fountain and sculptures, while historical buildings surround the piazza.

Just a few blocks southeast of the piazza is Ponte Vecchio, which is the old bridge with shops on either side, not of the river, but actually on the bridge.

About an hour before sunset, you will be heading to Piazza Michelangelo which has a beautiful view over the city. You may walk but the stairs and/or hills can be tiring, so it is worth it to get a taxi unless you want the exercise.

Head to dinner a few blocks away from the tourist attractions to a beautiful little trattoria.

If you haven’t shut down the restaurant, you may still have time to grab gelato after dinner! You can always head to a local bar too. On this trip, there are a few bars easily within walking distance, so if you don’t want to end your night when the restaurants close at around 9:30 pm, there are some great options to keep it going.

Head to our recommended local cafe or bakery for a great start to your day. For a traditional meal, enjoy a local baked good with an espresso.

We will set up a taxi ride for you or take a 15-minute walk west of the Duomo to get your rental car to head to the Pienza, in the Val d’Orcia. We can also make arrangements for a taxi to take you to one of the beautiful little towns in the valley, but we recommend having a car so you can move about freely.

Depending on your route, the drive to Pienza takes about 1 hour and 30 minutes to 2 hours, allowing you to see the beautiful views on your way.

Arrive in Pienza, heading to your accommodations to get settled in. If you have chosen the option to stay in the countryside, you will have to take a short drive through rolling hills to Pienza which is only 10 minutes away max. If you are in town, take a walk out of your front door.

Get acquainted with the stunning old town, which will be your base for the next few days to explore the countryside. Pienza holds traditional Renaissance architecture and is a UNESCO World Heritage Site. This small but charming town is renowned for its harmonious urban design, stunning views of the Tuscan countryside, and delectable local cuisine.

After exploring the little Tuscan town, you will be craving some local food and wine. We have some great options for food scattered about, no matter what you are looking for. From meat and cheese boards to plates of wild boar pasta, tons of traditional dishes are within reach. Get lunch at a little osteria. I recommend the wild boar pasta!

The wineries in the rolling hills are waiting for you after you eat. Walk to your car and head down the road less than 10 minutes to one of a few great local wineries.

Head to in town Pienza for dinner at a beautiful local place with small plates, so you can try many different dishes.

Head to a local cafe or bakery for a great start to your day. For a quick meal, enjoy a local baked good with an espresso.

Today, you will be embarking on a small road trip to different small towns in the Val d’Orcia, stopping at wineries in and/or between the following towns:

San Quirico d’Orcia- Some things to do include exploring the Renaissance Gardens of Horti Leonini, 12th century church, medieval walls and gates, Palazzo Chigi (renaissance palace), artisan workshops, and wine tasting.

Torrenieri – Torrenieri offers a tranquil and authentic Tuscan experience due to being less known than towns like Pienza and Montalcino. As all of these towns, there are also many wineries.

Montalcino – Great restaurants, wine, food, and scenery. Some things to do are the fortress, historic town center, museums and galleries, and of course, wine tasting. We recommend lunch at a beautiful small place here.

Castelnuovo dell’Abate – Some things to do include a 12th century romanesque church, the Abbey of Sant’Antimo, along with many surrounding wineries.

Castiglione d’Orcia – Some things to do include Rocca di Tentennano, a 13th century fortress and the historic center.

On your way back to Pienza, stop in Bagno Vignoni, at Parco dei Mulini, which is a hot spring. I would recommend not swimming in the public area here, but it is an interesting thing to see! Interested in a hot spring experience? Consider adding one for day 5!

Head back to Pienza for dinner at one of the many fantastic restaurants.

Head to a local cafe or bakery for a great start to your day. For a quick meal, enjoy a local baked good with an espresso.

When in Tuscany, after breakfast we drink wine. Head to Montepulciano to see the beautiful hillside town, the vineyards on the slopes, along with the many tasting rooms in town. Before arriving in Montepulciano, there is a winery just off the main road, with picturesque views of the rolling hills. We have a selection of 4 wineries in town to visit and, as always, many places to eat as well.

Walk to lunch 5 minutes away at a beautiful osteria. You will pass by the beautful Piazza Grande on your way. The osteria is run by a local family, offering typical dishes of Tuscany including Florentine steak, Tuscan meat boards, ribollita (stale bread soup, a personal favorite in Tuscany), and wild boar dishes (another personal favorite, anywhere in Tuscany).

Stroll back through town to the parking lot to depart the town of Montepulciano, to head to a winery in the countryside.

Production amount here is not a focus, but quality as it is a relatively small place compared to some others in the area.

On your way back to Pienza, have dinner at a beautiful restaurant in Montichiello, exploring the tiny town before departing for Pienza.

Head to a local cafe or bakery for a great start to your day. For a quick meal, enjoy a local baked good with an espresso.

On your last day in Tuscany, what better way to relax is there than lounging in the rolling hills sipping wine? Take a short drive out of town to a local winery down the road or you can head to your favorite one from the trip, as the furthest town on the itinerary is 40 minutes away.

For lunch and dinner you will dine at your preferred places on the trip or you may check out some recommendations that you have not yet had the opportunity to try.

For something else to do besides wineries, visit different agricultural producers nearby, such as pecorino cheese and olive oil.

In town are also a few interesting shops, but one you may not have thought of visiting is the grocery store. Check out what an Italian grocery store looks like if you haven’t as you may be surprised at the differences between Italy and home. Some others include a leather goods shop, cheese shop, and many clothing stores.

Head to our recommended local cafe or bakery for a great start to your day. For a quick meal, enjoy a local baked good with an espresso.

Drive back to Florence from Pienza, taking around 1 hour 30 min to 2 hours.

Piazza di Santa Maria Novella is a nice area where people congregate in front of one of the old main churches of the city. You can pass through this piazza on your walk after dropping off your rental car or we will have a taxi waiting to take you to your accommodation.

Today you will be entering the Duomo, exploring the beautiful cathedral that is larger than a football field. To round out the UNESCO World Heritage site, for an extra cost, you can also go inside Giotto’s Tower and the Baptistery.

Lunch today will be in a beautiful trattoria a few blocks away from the action. If you aren’t feeling a longer meal, I offer a few different options for each meal in my complete itineraries, so you will always be able to navigate to a great food experience.

The afternoon starts off with seeing David at the Accademia Gallery, which also houses many interesting items including old instruments such as violins by Antonio Stradivari. It is not a very large museum. If you are interested in a longer museum experience in addition to the Accademia, the Uffizi Gallery is another incredible museum in Florence, and definitely worth it if you find yourself with extra time.

Go across the river to a fantastic wine bar. They also have great snacks like antipasto (charcuterie) or sandwiches.

Stroll through the beautiful Boboli Gardens and Bardini Gardens located across the river from the Duomo. The beautiful gardens will provide a tranquil escape from the busy city, allowing you to wind down before traveling home the next day. Admire the many renaissance sculptures in the gardens.

Head up to Piazza Michelangelo via taxi to view the sunset over Florence before dinner.

Dine in a beautiful trattoria for your last night, enjoying Tuscan classics in a cozy setting.

Head to a local cafe or bakery for a great start to your day. You may want a larger meal this time to hold you over if you have a long trip.

If you have time, enjoy the beautiful streets an architecture sitting at a cafe with a drink while waiting your taxi.

A taxi will pick you up at your accommodation to take you to the airport for your flight.