International Travel, Itineraries & Trip Planning

How to Spend One Wine & Art-Filled Week in Tuscany

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I adore Tuscany. There’s not much that I don’t love about it, so when my partner and I went to Italy over Thanksgiving, we ended up spending the bulk of our time in Tuscany. Amazing food, world-renowned wines, rolling green hills, and art for days.

Here’s our itinerary for 1 week in Tuscany, ready for you to replicate. (I made a few tiny adjustments to include some favorites from past trips as well!)

1 week in Tuscany itinerary

Day 1: Explore Florence’s greatest hits

The Duomo Complex

Start your morning with an espresso and an Italian pastry or two at Scudieri. Despite being right next to the city’s famous Duomo complex, the spot actually has a lot of regulars.

Then get in line for the Duomo.

Florence cathedral

Officially the Cathedral of Santa Maria del Fiore, the Duomo is the centerpiece of Florentine architecture. The gorgeous pink, green, and white marble exterior, dotted with exquisite sculptures, is matched in the interior by the numerous panels of stained glass and the paintings under the dome.

Florence duomo painting

Access to the cathedral is free, but you’ll need a timed ticket in order to climb to the top of the dome.

That 18 Euro ticket also gives you access to the Baptistry, the Bell Tower, the Crypt, and the Museo dell’Opera del Duomo where many of the original artworks are held. (You should absolutely book ahead if you want to climb the dome as there are seldom day-of tickets for that.)

For lunch, go one street over to Fiaschetteria Nuvoli. There may be a wait since the place is so small, but once you make it down to the basement, you’ll be surrounded by coziness, wine, and delicious home cooking.

Uffizi Gallery

Make sure you’ve filled up on food before heading over to the Uffizi, perhaps the world’s greatest gallery of Renaissance art.

Unless you’re down for a ridiculously long wait, do yourself a favor and book Uffizi tickets ahead of time. And choose an early afternoon time so you have ample time to explore the museum without being interrupted by rumbling tummies or closing time.

The gallery is organized roughly in chronological order, which means works by any particular artist are generally in adjacent rooms. Take your time to view masterpieces and explore pieces new to you, or make yourself a “must see” list beforehand if you’re short on time.

Here are some of the masterpieces housed at the Uffizi.

Wine and views

When you’re ready to rest your feet after all that art, head toward the famous Ponte Vecchio (Old Bridge).

Likely built in the 10th century, Ponte Vecchio was the only bridge across the Arno River that was not destroyed by fleeing Germans during World War II. Today, it is a popular photo spot, especially at sunset.

Ponte Vecchio Florence

Walk across the bridge — which is packed with jewelry shops per a 16th-century royal decree that only allows such shops on it! — and find Le Volpi et L’Uva.

This local gem is tucked away in an alley but is an absolute must visit. The wine selection is phenomenal, as is the staff and the savory and sweet food selections.

schiacciata con l'uva

You’ll probably end up buying some wine to take home like we did.

Then walk up to Piazzale Michelangelo, the city’s most popular spot for sunset.

Is it going to be crowded? Yes. Is it still absolutely worth it? Also yes.

Where to stay in Florence: Hotel Cardinal of Florence. This small boutique hotel is so close to everything in Florence.

Day 2: More Florentine favorites

Florentine life

While Italy is filled with famous cathedrals, don’t miss the gorgeous synagogues either. Start your day at the Jewish Museum of Florence and learn about the history of Jewish people in the city.

Florence Jewish museum synagogue

Then head over to Sant’Ambrogio Market, a thoroughly Italian farmers’ market. Pick up some fresh fruit or Florentine schiacciata, or whatever your taste buds desire.

Stop inside for lunch at Trattoria da Rocco, a no-frills local favorite where wine is served in a jug and charged by how much you drink.

Leathers and nudes

Next up: more art. After all, you are in Florence.

If you went to the Uffizi and was wondering where Michelangelo’s David was, head over to the Accademia.

While not as famous as the Uffizi, the Accademia nonetheless draws crowds for this famous statue. And yes, say what you will about David’s anatomical proportions.

After you’re done at the art gallery, get some fresh air and explore the famous San Lorenzo leather market, home of all sorts of potential presents, for others or for yourself. (I won’t lie though, the quality of the leather at this market has seemingly gone down in recent years. There are still some good finds, though.)

San Lorenzo leather market Florence

And then pop into the nearby Mercato Central for a dinner experience that will satisfy everyone in your group.

Basically a gourmet food court, Mercato Central has all sorts of delicious Italian specials as well as options like sushi and Chinese hand-pulled noodles. There are also beer taps and wine bars.

Hold off on dessert though and walk over to My Sugar instead for some delicious, artisanal gelato. You can’t go wrong with their black sesame flavor!

My Sugar gelato Florence

Day 3: Siena, the heart of Tuscany

In the a.m., take a 90-minute train from Florence to Siena, which is like the former’s smaller, less touristy, and more charming sibling.

As with Florence, start your exploration of Siena with its Duomo complex. If you were wowed by the Florence cathedral, the Siena one will impress you even more.

Siena cathedral

The white and green-black marble exterior may seem more austere than that of the Florence cathedral, but the inside of the Siena cathedral is absolutely spectacular. The floors have these intricate mosaic artworks, and the walls are lined with various sculptures and stained glass panels.

Siena cathedral mosaic flooring

Don’t miss the adjacent Piccolomini Library, where medieval choir books are surrounded by Renaissance frescos, all topped with a stunning painted ceiling.

Admission to both the cathedral and the library come in the form of the OPA SI pass, which also gives you access to the Baptistry, the Crypt, the museum, and a panoramic view from the unfinished facade of another cathedral.

If you want an even more special experience, you can buy the Gates of Heaven All-Inclusive, which allows you to go up to the dome and roof areas of the cathedral. (More on this experience and whether it was worth it coming later!)

The tickets are valid for 3 consecutive days, so you can always space out your visit to the various parts of the Duomo complex as you wish. Since you won’t be arriving in Siena until mid-day, the Duomo complex will likely take you most of the rest of the daylight hours, if you decide to do it all in one go.

For your lunch break, swing by the nearby Il Bargello. The small storefront leads into a basement dining room and serves up delicious Tuscan favorites along with a large selection of wine. Perfect for a long leisurely lunch.

Il Bargello Siena

Other suggestions for delicious food and wine breaks:

  • Rombo & Vas – part bakery, part wine tasting room featuring Chiantis from the Villa a Sesta winery
  • Vineria Il Murello – part wine bar, part restaurant, part local late-night hangout

Where to stay in Siena: B&B Quattro Cantoni. The location of this spot is perfect, so close to all the main attractions without being in the middle of any noisy areas. The rooms are small as common in Europe, but 100% meets your needs. 

Day 4: It’s time for Chianti

Don’t worry, we’ll come back to Siena! But for now, pick up a rental car and head out to the world-famous Chianti wine region.

We booked an Airbnb Experience with Montemaggio, a small, female-owned, organic winery nestled in the woods of Radda in Chianti.

Despite the weather being foggily uncooperative, we had an amazing time on the beautiful grounds of the winery. Our host taught us so much about Chianti Classico wines, their production process, and the legend of the black rooster symbol of the region.

And of course, we had delightful tastings — sword opening of the sparkling chardonnay included!

After your first Tuscan vineyard experience, go into Radda in Chianti and explore the first of your tiny Tuscan towns. So much adorableness and cute alleyways everywhere you go.

Settle in for the night in nearby Castelnuovo Berardenga, a small commune that’s the perfect base for visiting Tuscany’s many wine regions.

Where to stay in Castelnuovo Berardenga: Casa Cernano. Have a true Tuscan countryside experience at this 14th-century farmhouse. It’s seriously picture perfect.

Casa Cernano Castelnuovo Berardenga

Day 5: Wine and thermal baths

Montepulciano region

While Chianti is perhaps the most well-known to the average wine drinker in the U.S., the Tuscany region is home to many other famous wines. With our base in Castelnuovo Berardenga, we chose to focus on Chianti, Montelpuciano, and Montalcino.

Montepulciano, home of the famous Vino Nobile di Montepulciano, was perhaps our favorite. There, we visited both actual vineyards and off-site tasting rooms in town.

Our favorites included:

  • Tana Gatta, a tiny family operation that only produces 10,000 bottles a year
  • Cantine Contucci, the cellar and tasting room from a family that has been making wine in Montepulciano since the Renaissance
Contucci winery Montepulciano
With Adamo, the longtime winemaker for the Contucci family

Besides the tasty wines, there’s also just so much gorgeous rolling hills and vineyards to take in.

Montepulciano Tuscany

Bagni San Filippo

Once you’re ready for something a little different, head south toward Bagni San Filippo, where you can find natural thermal baths to relax in.

Follow the street signs and footpaths to find the various pools to bathe in. Just make sure to not do so right under this formation known as the White Whale. (Heads-up: The pools are known to be nice and hot during the warmer months, though during the colder and rainier months, they’re merely warm.)

Bagni San Filippo Tuscany

Day 6: Countryside strolls and wines

Castelnuovo Berardenga

Before you leave Castelnuovo Berardenga, make sure to walk around the town a little bit.

It’s fairly small, so it won’t take you too long. Explore the city center, the local churches, the morning markets, the grand Villa Chigi Saracini, and just generally enjoy strolling through the town.

Castelnuovo Berardenga
One of the fun findings walking around town.

Montalcino region

Then head to Montalcino, home of Brunello di Montalcino, one of the most expensive and most famous Italian wines.

Like all the other wine areas in the Tuscany region, Montalcino’s sprawling vineyards are more than easy on the eyes. My favorite among the ones we visited is Solaria, aka Azienda Agricola Patrizia Cencioni.

Solaria Montalcino Tuscany
The tasting room of Solaria

Tuscan food at its best

Then, as promised, it’s time to head back to Siena.

Drop off your rental car and get ready for a ridiculously delicious dinner at Taverna di San Giuseppe.

The kitchen does such an amazing job with basically everything. The pasta, the meats, and especially the tiramisu. I know that sounds basic, but believe me, get that tiramisu. We still can’t stop talking or dreaming about it.

Make sure to make a reservation well ahead of time. It’s the perfect last dinner to end your time in Tuscany.

Day 7: Savor the rest of Siena

Start the last day of your 1 week in Tuscany with breakfast at Bar Pasticceria Nannini.

Not only is it a great breakfast spot, it also has so many Tuscan specialties and wines for sale. Just in case you wanted to take more goodies home.

Feel free to get your breakfast to go and sit in the Piazza del Campo, the city’s huge, shell-shaped square. (Is it still a square if it’s shell-shaped?)

Then walk over to the Basilica Cateriniana San Domenico.

No photos are allowed inside so I can’t show you it, but you should absolutely visit. Its amazing stained glass pieces are unlike most found in churches, so incredibly vibrant and moving.

The church also includes relics of St. Catherine of Siena, for whom it is named. Yep, including her head. Definitely not for the queasy.

If you need a breather afterward, head out to the left side of the church near the crypt for some gorgeous views of the city.

Siena panorama

And for one last stop before you head to the train station or airport, go to Bar Gelateria Nannini for some delicious gelato. What better way to end your week in Tuscany?

Are you ready to spend some time in Tuscany? Pin it to share it!

1 week in Tuscany itinerary

10 thoughts on “How to Spend One Wine & Art-Filled Week in Tuscany

  1. Yes, wine everyday! I love this! And what even is Black Sesame flavoured ice cream? I am so curious. A really detailed guide, which covers a lot without feeling rushed. I am wondering if you remember the cost of the restaurant you visited? I have been to Tuscany and would totally love to go back and see what I missed the last time.

    1. I was curious, too! Think toasted black sesame and mix that into a vanilla base. (I don’t think that’s how they make it, just trying to describe it.)
      A lot of the places were between 15-20 euros a person (including wine). San Giuseppe was about 64 euros per person but including 4 courses and a bottle of wine plus dessert drinks!

  2. I absolutely love Siena and Chianti! I could spend months there. I didn’t know about the thermal baths so I’ll have to check them out next tim!

  3. I can’t believe I skipped over Tuscany on my trip to Italy – your blog post is really making me regret that, but the good news is I have so many reasons to go back now! The picture of the foggy duomo is so enticing, that drew me to this article immediately. Looks like such a beautiful place.

  4. […] you have more time to spend in this lovely region? Check out this one-week itinerary for Tuscany for […]

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