Tuscany Itinerary for First-Timers: 7 Days Countryside + 3 Days Florence (Best Stops & Stays)

After spending a few weeks exploring Tuscany for a second time, I have to say it’s a region I could visit again and again. I’ve combined the best of those trips into an unhurried 7 to 10-day Tuscany itinerary to help first-time visitors make the most of their time.

For a first trip to Tuscany, I recommend a 10-day itinerary split into two parts: 7 days in the countryside (through places like Val d’Orcia, Siena, and San Gimignano) followed by 3 days in Florence. This structure keeps driving efficient, avoids backtracking, and gives you time to enjoy both the countryside’s slower rhythm and Florence’s art, food, and historic center without rushing.

When it comes to things to do in Tuscany, it seems like the choices are endless. You can explore the grand city of Florence, the pint-size villages of Chianti and Val d’Orcia, or historic hill towns like San Gimignano, Siena, and Montepulciano. Rooted in winemaking and agriculture, the region is vibrantly rich in culture. I don’t think you can go wrong with how you spend a slow day in the Tuscan Valley.

About the Tuscany Region of Italy

Often referred to as the heart of Italy, Tuscany is a region made up of ten provinces. Florence, Siena, Pisa, Lucca, Arezzo, Livorno, Grosseto, Pistoia, Prato, and Massa-Carrara are the ones included. Each of these areas has its own character and charm, but the most popular to visit are Florence, Siena, and Pisa, along with the rolling countryside of Chianti and the Val d’Orcia, where you’ll find the hill towns and landscapes Tuscany is famous for.

My approach to visiting Tuscany is to focus on the main sights of Florence and its nearby countryside, starting in San Gimignano and down to Val d’Orcia. The truth is, there is a lot to see in Tuscany, and it could take several weeks to do it all, so I’ve narrowed in on the highlights. You can certainly cut out some of the stops and switch in others if you want to; that’s the beauty of the flexibility of this itinerary.

Read on for my complete 7 to 10-day Tuscany itinerary.

Short on Time? Here’s the Ultimate Tuscany Itinerary (One Week Countryside + 3 Days Florence:

Stop 1: San Gimignano Region — 2 nights

Start your trip in the countryside near San Gimignano, picking up a rental car on arrival and easing into Tuscany at a slower pace. Spend your first afternoon in nearby Volterra for a historic hill town introduction. Dedicate a full day to San Gimignano, arriving early to explore its towers and piazzas before the crowds. Round out the stop with a relaxed afternoon of wine tasting either close to San Gimignano or in Chianti.

1. Castelfalfi ($$$$ / Where I Stayed), for the best luxury resort with multiple restaurants, a spa, and expansive grounds
2. Borgo Pignano ($$$$ / Where I Stayed), for the best luxury boutique stay on a working estate with peaceful countryside views
3. 2 Bedroom Luxury Medieval Tower Penthouse, for the best one-of-a-kind stay
4. 2 Bedroom Apartment with Views, for the best countryside views

Stop 2: Siena — 2 nights

Road trip south with a scenic drive to Siena, stopping briefly in Monteriggioni along the way. Siena is worth more than a quick visit, so plan time to fully experience it: wandering Piazza del Campo, strolling the historic streets, and enjoying long meals. Your full day is best spent exploring Siena’s cathedral complex and viewpoints, finishing with sunset views over the city.

1. Grand Hotel Continental ($$$), for the best luxury hotel inside Siena’s historic center, set in a restored palazzo
2. Hotel Athena ($$), for the best boutique stay with easier car access and walkable distance to the center
3. 1 Bedroom Historic Apartment with Incredible View (Where We Stayed), for the best classic Siena stay with an unforgettable basilica view
4. 2 Bedroom Apartment near Piazza del Campo, for the best spacious setup for couples or friends who want to stay steps from it all

Stop 3: Val d’Orcia — 3 nights

Base yourself in Val d’Orcia for the most iconic Tuscan landscapes, staying near Pienza, Montalcino, or Montepulciano. Days here are slow and scenic: a village stroll, one standout meal, and time to take in the views. Visit Pienza and Monticchiello, enjoy long lunches in the countryside, soak in Bagno Vignoni, and finish with wine-focused afternoons in Montalcino and Montepulciano.

1. Lupaia ($$$$ / Where I Stayed), for a luxury boutique hideaway with incredible views and a standout restaurant
2. Rosewood Castiglion del Bosco ($$$$), for the best full-service Tuscan resort with vineyards, spa, and golf
3. Casa Newton ($$$), for the best design-forward countryside stay with a modern, relaxed feel
4. La Bandita Townhouse ($$), for the best in-village stay in Pienza with modern design and walkable dining
5. La Fonte Agriturismo Agriristoro ($), for the best simple agriturismo stay surrounded by open fields near Pienza
6. 2 Bedroom Garden Apartment near Pienza (Where I Stayed), for the best Val d’Orcia views
7. 2 Bedroom Historic Apartment in Pienza, for the best Pienza town-center rental

Stop 4: Florence — 3 nights

Finish with 3 full days in Florence. Use your time to explore sights like Piazza della Repubblica, the Cathedral of Santa Maria del Fiore (the Duomo itself), and Brunelleschi’s Dome (Cupola del Brunelleschi). Book a Sunset Food & Wine Tour through Oltrarno, and don’t miss a morning at Palazzo Pitti and Giardino di Boboli (Boboli Gardens) with nearby artisan shopping.

Hotels

1. Hotel Number Nine ($$$ / Where I Stayed), for the best boutique hotel with a spa and central location near San Lorenzo
2. Hotel Savoy ($$$), for the best luxury hotel in the heart of Florence’s historic center
3. The Artists’ Palace Florence ($$), for the best apartment-style suites near Piazza San Lorenzo
4. Plaza Hotel Lucchesi ($$$), for the best river-view hotel with a rooftop pool near Santa Croce
5. Bernini Palace ($$$ / Where I Stayed), for the best old-world luxury stay steps from Piazza della Signoria
6. La Maison du Sage ($$), for the best refined boutique hotel in a quieter area near Santa Croce
7. Hotel Lungarno ($$$), for the best luxury hotel in Oltrarno with river views and a design focus
8. Hotel Palazzo Guadagni ($$), for the best Oltrarno stay with rooftop views over Santo Spirito

Airbnbs

1. 2 Bedroom Oltrarno Apartment with Panoramic Terrace, for the best rooftop views in Oltrarno with a terrace overlooking Santo Spirito
2. 1 Bedroom Penthouse with Terrace and Jacuzzi, for the best luxury rental on Via Tornabuoni with a private terrace
3. 1 Bedroom Historic Apartment in Santo Spirito, for the best character-filled Oltrarno stay with a frescoed bedroom and veranda

Travel Tips

1. Rent a Car — The best way to explore Tuscany is by driving yourself. We use Discover Cars for our rental cars in Europe, choose full coverage insurance, and opt for trusted companies like Alamo, Hertz, or Sixt. Renting a car and driving in Tuscany is quite easy. Book your car with Discover Cars here.
2. Get Cell Data Before You Arrive — We use Holafly unlimited data eSIMs for all international travel and recommend installing yours before you land. Maps, directions, and translations all work the moment you arrive. Pre-Purchase your Holafly eSIM here.
3. Book an Airport Transfer in Advance — For a smooth arrival, I recommend booking your airport transfer ahead of time with Welcome Pickups. They meet you at arrivals and handle the ride into the city so you can skip the taxi line.

Helpful Guides to Plan Your Trip

To help you plan your time in Tuscany in more detail, I’ve put together several guides you can use alongside this itinerary. For the countryside portion, my guides to San Gimignano, Val d’Orcia, Siena, Montepulciano, Pienza, and Montalcino go deeper into what to see, how to pace your visit, and where to eat and drink. If you’re deciding where to base yourself, my guide on where to stay in Tuscany breaks down the best areas and hotels across the region.

For the Florence portion, be sure to reference my 3-day Florence itinerary, Florence travel guide, where to stay in Florence guide, and guide to Florence with young kids, which cover neighborhoods, major sights, curated hotels, and practical tips for exploring the city. And if Tuscany is part of a longer first trip to Italy, my 12-night first-timers Italy itinerary shows how Tuscany fits into a broader Rome–Florence–countryside route. For more on Italy, start with my list of the best cities in Italy and 10-day Italy itinerary.

The Ultimate Tuscany Itinerary: 7 to 10 Days

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Things to Know Before Visiting Tuscany

Getting Around Tuscany (Why a Rental Car Is Essential)

If you’re going to explore Tuscany, a rental car is the way to do it. Public transport is incredibly limited here, so I recommend picking up your rental car on arrival at the airport or train station in your arriving city.

Rental Car Tip: We use Discover Cars for our rental cars in Europe, choose full coverage insurance, and opt for trusted companies like Alamo, Hertz, or Sixt.

ZTLs in Tuscany (What You Need to Know Before Driving)

Many historic centers in Tuscany, including Florence, have ZTLs (Limited Traffic Zones) where driving is restricted. Entering a ZTL without authorization can result in fines, often sent weeks or months later. When driving, always confirm hotel access instructions in advance, and avoid following GPS directions directly into historic centers unless explicitly advised.

When is the Best Month to Visit Tuscany?

The best months to visit Tuscany, in my opinion, are the fall months of September, October, and November. It’s when the weather is a touch cooler, crowds start to dissipate, and the region feels incredible in fall. I love the months of September through early November here. If you’re envisioning pool days, just know that June through early September are your “swim-friendly” months, but they also come with crowds.

Is it Crowded in Tuscany?

Yes and no. The crowds are at their peak in June through September, and really don’t fully disappear until mid-October. The beauty of Tuscany is that, because it is a large region with dozens of towns, you can usually avoid the peak crowds by going to smaller villages. Also, an earlier start to the day meaningfully increases the odds of enjoying villages before the masses come.

How Many Days Do You Need in Tuscany?

Tuscany is one of those regions you could visit two to three times over to fully experience. For a first-time trip, I’d set aside a minimum of a week for the countryside, and a few days for Florence. This itinerary is set up exactly that way, with 7 days in the Tuscan countryside and 3 days for Florence. This balanced pace will let you experience both without rushing.

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7 to 10 Day Tuscany Itinerary

• Day 1: Fly into Tuscany, Arrive to San Gimignano
• Day 2: San Gimignano and Wine
• Day 3: Monteriggioni and Arriving in Siena
• Day 4: A Full Day in Siena
• Day 5: Head to Val d’Orcia + Pienza
• Day 6: Monticchiello and Montalcino
• Day 7: Bagno Vignoni, Agriturismo lunch, and Montepulciano
• Day 8: Drive to Florence
• Day 9: Florence Full Day
• Day 10: Florence Full Day

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Editor’s Note on This 7-to-10-Day Tuscany Itinerary

How I plan my trips is slow and centered around meaningful experiences. And while I’d vote for you to spend 2 weeks in Tuscany alone, I recognize not everyone wants to spend their entire vacation in a single region. So I’ve put together a conscious, geography-smart itinerary for Tuscany to help make the most of your time. This itinerary is split into a week in the countryside and the additional 3 days in Florence at the end (days 8, 9, and 10).

If you don’t want to start in the countryside, you could start with Florence, get your car after your days there, and continue to the countryside. And then end in Rome for a final week, dropping off your car rental in Rome. I have this itinerary set with picking up your car rental on arrival, and ending back in Florence. Either way works; just know you don’t need a car rental in Florence, and it is nearly impossible to drive into the city center because of the ZTL (Limited Traffic Zones).

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Day 1: Welcome to Tuscany, Arrive in San Gimignano Region (2 Nights)

Arriving in Tuscany

When it comes to arriving in Tuscany, there are two main airports to pick from. The first is Pisa International Airport, and the main one is Florence Airport. While Florence Airport is closer to Florence and most of the Tuscany spots in this itinerary, you can still fly into Pisa, as it has more flight options, and is only about an hour out of the city (On our most recent visit to the region, we flew into Pisa from Sardinia and hired a private transfer to Florence with Welcome Pickups and it was quite easy). So, depending on how you arrange the itinerary, don’t skip Pisa as an option if you’re not finding the flight you want.

On arrival, I would rent a car at the airport and make my drive to the first regional point in Tuscany, San Gimignano.

Rental Car Tip: We use Discover Cars because it’s easy to arrange one-way drop-off rentals with reputable companies like Hertz or Sixt.

For hotels, I’ve included two options below: Castelfalfi and Borgo Pignano. Both are within earshot of San Gimignano and offer entirely different hotel experiences.

Castelfalfi is a resort hotel built around a village and has several restaurants, a pool, a spa, and grounds to enjoy. Borgo Pignano is a boutique historic hotel, set across a cluster of buildings (once a borgo) on a working farm, with a restaurant and pool. We stayed at both hotels on our Tuscany itinerary (if you have time, I’d do both because they are entirely different experiences).

Where to Stay in San Gimignano Region (2 Nights)

Hotels

1. Castelfalfi ($$$$ / Where I Stayed), for the best luxury resort with multiple restaurants, a spa, and expansive grounds
2. Borgo Pignano ($$$$ / Where I Stayed), for the best luxury boutique stay on a working estate with peaceful countryside views

Airbnbs

1. 2 Bedroom Luxury Medieval Tower Penthouse, for the best one-of-a-kind stay
2. 2 Bedroom Apartment with Views, for the best countryside views
3. 2 Bedroom Garden Apartment near Piazza della Cisterna, for the best central historic stay

First Day in San Gimignano Region

Get settled into your accommodations and begin your afternoon with time in Volterra. About a 30-minute drive from either hotel, Volterra is one of the historic villages that often gets overlooked for San Gimignano. Rich in history, it feels authentically local.

You’ll only need about 2 hours to visit this village, which is why it makes for a great late afternoon arrival for a quick taste of Tuscany. Stroll into the historical center, pass by the Cattedrale di Santa Maria Assunta. For great views, make the climb to the top of Palazzo dei Priori, which overlooks the Piazza dei Priori, the heart of Volterra. I recommend that, as you walk around, you find the street Via Lungo le Mura del Mandorlo, which overlooks the ruins of Teatro Romano di Velathri (Volterra), or the Roman Theatre.

Other highlights for me in Volterra were spending time in the Museo Etrusco Mario Guarnacci to understand the Etruscan era that shaped the city. This street that the museum is on feels incredibly charming and is full of local shops.

When it comes to dinner, I’d recommend either staying in Volterra for a meal at La Vecchia Lira or Hostaria Il Sacco Fiorentino. We had an incredible lunch at Hostaria, their housemade pastas with truffle were to die for. If you want something more elevated, book in for the Michelin-Green star Restaurant at Borgo Pignano. The multi-course menu is a journey through Tuscan cuisine, and one of the most memorable meals we had in Tuscany.

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Day 2: San Gimignano and Wine

The Morning

Begin with an early-morning drive and make your way to San Gimignano. Often dubbed as the “Manhattan of Tuscany” with its several towers, it’s an icon of Tuscany. So much so that it draws in heavy crowds. I recommend arriving by 9 am to enjoy the city sans the people.

You really need a few hours to enjoy the village, so come in with good walking shoes to enjoy the sights. I recommend picking up the San Gimignano pass as it gives you two-day access to the civic museums, including Palazzo Comunale, Torre Grossa, Contemporary Art Raffaele De Grada, the Duomo di San Gimignano, and more. Begin your time in the UNESCO-listed town by walking up to the Piazza del Duomo.

From there, head for a walk to Piazza della Cisterna and don’t miss  Palazzo Comunale (also known as the Palazzo del Popolo). Don’t miss the churches of San Gimignano; the shining star is Collegiata di Santa Maria Assunta, with its incredible frescoes. Adjacent to it is the Torre Grossa, the tower you can climb to the top of for stunning views over the valley.

While in town, a few other highlights to keep an eye out for are the main street, which has several shops and boutiques to peruse. One standout place is Gelateria Dondoli, often dubbed the best ice cream in Italy. I’ve stopped in once, and it was good. If the line is super long, I’d skip it. For lunch, I’d eat at Ristorante Peruca or La Vecchia Nicchia.

The Afternoon to Evening

For the afternoon, I’d turn your sights to wine. You have two options here in terms of experiencing wine. You can either stay near San Gimignano, stopping into a winery or two, or make the 45-60 minute drive out to Chianti. Whichever you prefer, just know that there are endless options for wine.

My preference for something close by to San Gimignano is to book a wine tasting at Podere La Marronaia, which is only 5 minutes outside of the city. It’s a great introduction to this region’s wine if you’re not looking to go to Chianti. Another memorable nearby option is the incredible Tenuta Torciano, which requires reservations.

If you’re looking to go wine tasting in Chianti, I’d head towards places like Radda in Chianti, Castellina in Chianti, and Gaiole in Chianti to try the DOCG Chianti Classico wine. A few wineries to consider are Cantina Antinori, San Felice, and Vallepicciola. If you feel overwhelmed picking out and planning a wine day, my recommendation is to hop on a Chianti wine tour like this Small Group Tour.

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Day 3: Monteriggioni and Arriving in Siena (2 Nights)

On this day, you’ll road trip down to Siena. It’s one of the cities I completely skipped on my first trip to Tuscany, and I deeply regretted it. While many only visit for an afternoon, I do think it’s worth spending a night or two to really take in the half-dozen sights.

As you depart the San Gimignano region, you will pass by the small town of Monteriggioni on the way to Siena. This is a wonderful stopping point to hop into the village for an hour. You can go for a quick stroll, see the fortified village, and walk the outer walls. For lunch, I’d recommend making a reservation at Bar dell’Orso just outside the village, which is quite possibly the most popular roadside restaurant in Tuscany. Think Tuscan classics, charcuterie, and all the other favorites in a quaint osteria setting.

From there, drive to Siena to begin your time. When choosing your accommodations, it’s important to know that you will not be able to park your car in the city center. You will park at the very bottom and have to walk up a hill and utilize the escalators. Your accommodations can help direct you, but if you’re traveling with large luggage, be prepared for a climb.

Where to Stay in Siena (2 Nights)

Hotels

1. Grand Hotel Continental ($$$), for the best luxury hotel inside Siena’s historic center, set in a restored palazzo
2. Hotel Athena ($$), for the best boutique stay with easier car access and walkable distance to the center

Airbnbs

1. 1 Bedroom Historic Apartment with Incredible View (Where We Stayed), for the best classic Siena stay with an unforgettable basilica view
2. 2 Bedroom Apartment near Piazza del Campo, for the best spacious setup for couples or friends who want to stay steps from it all
3. 2 Bedroom Apartment on Piazza del Campo with Terrace Views, for the best front-row seat to Siena’s most iconic square
4. 2 Bedroom Top-Floor Apartment with Rooftop Terrace, for the best morning coffee spot above the rooftops

The Afternoon in Siena

For your first afternoon in Siena, make your way into the popular Piazza del Campo, the heart of the city. It is so lively, and you feel like you’ve stepped back into time. The towering Torre del Mangia is there, which you can walk to the top of if you’d like to get a bird’s eye view of Siena.

Go for a stroll down the main street of Via di Città, it’s home to stores like Antica Drogheria Manganelli 1879, Cappelleria Bertacchi, Manufactus Siena, and more. You can also pop into the Palazzo delle Papesse if you have time to see its current exhibits.

For dinner, make an advance reservation at either Osteria Le Logge, Osteria La Sosta di Violante – La corte di San Giorgio, La Taverna di San Giuseppe, or Osteria Permalico. These are the restaurants I’d be looking to make reservations at while in Siena for both lunch and dinner. All of these places need advance reservations as they are so popular.

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Day 4: A Full Day in Siena

The Morning

What a joy it is to wake up in Siena and be there before the tours arrive. Wake up early, and go for a stroll because the city feels entirely different without the people (If you do, you’ll have the city almost entirely to yourself until at least 9 am). Head back to Piazza del Campo, passing under one of the many arches that lead into the grand square. Go for a walk over to the Santa Maria della Scala and soak in its facade, and see the Siena Cathedral. For the best cup of coffee in town, head to Torrefazione Fiorella, which opens every day except Sunday at 7 am (this was a daily stop for us during our visit).

As you begin to craft your day in Siena, this is how I would go about it. As it starts to get busy in the city center, I’d make my way out to Basilica Cateriniana San Domenico first. It’s a stunning Gothic Cathedral, and from the road there, it looks back to the Siena citadel. Along the way, if the hours work out, Santuario Casa di Santa Caterina is a sanctuary you can visit, but it has limited opening times.

For lunch, I’d book in from the list of Osteria Le Logge, Osteria La Sosta di Violante – La Corte di San Giorgio, La Taverna di San Giuseppe, or Osteria Permalico. Afterward, enjoy a stroll around Siena, taking in many viewpoints, such as from the Fontanina della Contrada Capitana dell’Onda or the Torre Mangia.

The Afternoon

You’ve come all this way to Siena to see its grand dame — the Duomo. I’d recommend spending the late afternoon into the early evening in this part of Siena. I’d start with the Santa Maria della Scala to see the current exhibits and frescoes. From there, pass through the Piazza del Duomo and make your way into the Siena Cathedral.

The Siena Duomo (or Cathedral) alone is just an absolute stunner, and you can spend easily 30-minutes here soaking in the details. For me, the real highlight of the cathedral was time in the Piccolomini Library, one of the most beautiful, airy libraries I’ve been into in my lifetime. It’s a small room housed inside the cathedral, don’t miss this. My recommendation is to go to the cathedral around 4 pm to miss the peak crowds, which usually depart by 3.

Travel Tip: Early morning (pictured above) is the best time to take in the Cathedral’s exterior, as it’ll be completely free of crowds until about 9 am.

After the cathedral, make your way over to the Facciatone, an observation deck (beware: some serious steps!) that offers a stunning view of Siena and back to the Duomo. It’s first-come, first-served, so know that they only allow one group at a time here. I happened to time it with sunset around 5:00 pm and had the most beautiful views over Siena. It’s inside the Museo dell’Opera, so consider making time to see these sights as well.

Travel Tips for the Duomo Complex of Siena

I don’t think doing the ‘Gate of Heaven’ tour is worth it. It’s the small group guided tour of the roof and terraces of the cathedral itself, limited to 18 people. I think the views from the Facciatone are much better as you’re looking back at the cathedral itself. I did both, and preferred the Facciatone. The Baptistery of San Giovanni is worth stopping into; it’s just on the other side of the cathedral, and you only need about 10 minutes to see it.

Travel Tip: I recommend getting the Opa Si Pass, which includes Siena Cathedral, Piccolomini Library, the Crypt, the Baptistery, the Cathedral Museum, and the Panorama of the Unfinished Façade. If you plan to do the “Porta del Cielo” or “Gate of Heaven”, then get the Porta del Cielo Pass, which includes everything.

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Day 5: Head to Val d’Orcia (3 nights) + Pienza

For your final 3 nights in Tuscany, make your way to the beloved Val d’Orcia. After two trips in Tuscany, this is my favorite region or part of Tuscany. It’s this beautiful landscape, set with its hilltop towns, two prominent DOCG wine regions, and several incredible hotels and restaurants to enjoy. It really has it all, so make the time to spend a few days here to do several day trips.

After Siena, my preference is to pick a base between Montalcino and Pienza or Pienza and Montepulciano. I stayed near Pienza this time, and loved the ease of location. I have an entire guide on where to stay in Tuscany, which details the Val d’Orcia. Just know you’ll always be a 15-30-minute drive to a hill town or a sight to see!

Where to Stay in Val d’Orcia (3 Nights)

Hotels

1. Lupaia ($$$$ / Where I Stayed), for a luxury boutique hideaway with incredible views and a standout restaurant
2. Rosewood Castiglion del Bosco ($$$$), for a classic Tuscan resort with vineyards, spa, and golf
3. Casa Newton ($$$), for a chic design-forward stay in the countryside
4. La Bandita Townhouse ($$), for a stylish in-village stay right in the heart of Pienza
5. La Fonte Agriturismo Agriristoro ($), for a simple, charming farmhouse stay surrounded by fields

Airbnbs

1. 2 Bedroom Garden Apartment near Pienza (Where I Stayed), for the best Val d’Orcia views
2. 2 Bedroom Historic Apartment in Pienza, for the best Pienza town-center rental
3. 2 Bedroom Apartment in Montepulciano, for the best panoramic city stay
4. Studio Loft in Montepulciano, for the best walkable historic rental
5. 2 Bedroom Panoramic Country Suite in Montalcino, for the best scenic Val d’Orcia base
6. 2 Bedroom House in Montalcino, for the best central Tuscan stay

For your first afternoon in Val d’Orcia, I’d make your way to the village of Pienza. It’s my favorite village in this area, and it’s the best spot for a leisurely stroll, with plenty to do. Pope Pius II designed the village in the 15th century as his “ideal village,” and it has so much charm. Step back in time in Piazza Pio II, pop into the  Palazzo Piccolomini, a UNESCO World Heritage Site known for its perfectly proportioned architecture, and don’t miss the incredible views from the outer walls.

In the village, it’s known for pecorino, so if you spot a cheese store, stop in to try and buy some to take home. Salumeria Gastronomia del Corso Pienza is my favorite cheese store in town. When it comes to dinner, Sette di Vino is my choice for an understated yet fantastic local meal. The restaurant at La Bandita Townhouse Hotel, and PROSIT are two other great choices.

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Day 6: Monticchiello, Dopolavoro La Foce, and Montalcino

The Morning

In this part of Tuscany, time seems to move slowly, and meals are long. I’d plan specifically around 2-3 things a day: a village, one standout meal, and views. On your first full day, begin your morning in the pint-sized village of Monticchiello. The historic village is worthy of an hour’s stroll. What draws visitors is the panoramic view of the nearby, iconic zigzag, cypress-lined streets from this viewpoint.

Afterward, go for a scenic drive to your next destination for lunch. Along the way, consider stopping by Mulino Val d’Orcia to pick up some organic dried pasta to bring home and walk the grounds. Your lunch today is at the incredible Dopolavoro La Foce, a top contender for best food in this region. With a reservation, enjoy a slow lunch over Tuscan classics like the Florentine steak, steak tartar, and housemade pici pasta.

The Afternoon

For your afternoon, make the drive across the valley over to one of my favorite local villages, Montalcino. It’s a hilltop gem, and one worth spending 2-4 hours visiting. The town is framed by fortified walls and dominated by the Rocca di Montalcino, a 14th-century fortress. But it’s also known for its DOCG wine, the Brunello di Montalcino DOCG.

Several spots in town are more than happy to pour a glass of wine to enjoy, so make the time to stop into places like Caffe Fiaschetteria or Enoteca di Piazza. Stroll to the top of the village to Concattedrale del Santissimo Salvatore, a church with Neoclassical style in a Romanesque building. Don’t miss the  Palazzo dei Priori set in the  Piazza del Popolo.

If you love a photographic sunset spot, I’d set your eyes on Cappella della Madonna di Vitaleta. One of the most popular sunset spots in this area, it’s a small chapel framed by six cypress trees. Afterward, I’d make a reservation for dinner at the Restaurant at Lupaia for a cozy, multi-course menu of the day.

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Day 7: Bagno Vignoni, Podere Il Casale, and Montepulciano

Morning

For your final day in Val d’Orcia, I’d begin with a late morning visit to Bagno Vignoni. A small village set around a historic thermal bath, it’s a stunning sight and worth visiting. You can’t swim in the main thermal bath in the center, but you can either book a day pass at a place like Terme Hotel Le Terme or make the short walk to Parco dei Mulini for the free baths there.

Afterward, I’d make a reservation for lunch at what was my favorite restaurant of the trip: Podere Il Casale. This working agriturismo perched just above the village of Pienza is one of the best spots in the valley. While you can do tours here, I’d recommend coming in for lunch on its terrace. You’ll try local food, taste their wines, and enjoy a menu featuring all of their ingredients from the farm. After our meal, we spent another hour with our daughter, visiting the animals and playing on the small play structure on the property.

Afternoon

To end your last afternoon, make your way to Montepulciano. After visiting multiple times, I find there are two ways to go about visiting this popular village: either show up early or come in later in the afternoon. You’ll only need about 3 hours or so to visit, so a 3 pm arrival is perfect.

On arrival, make your way up the main street to Piazza Grande. Know that this is very steep and will take some time. There is a small train that goes up every 30 minutes or so from the bottom gate near Porta al Prato. Some sights to see here include the Palazzo Comunale and the Museo Civico Pinacoteca Crociani, but the main draw is wine.

Montepulciano is known for its red wine, Montepulciano d’Abruzzo DOCG. There are several historic antinas and underground cellars here, for which you’ll need a reservation for a tour, like De’ Ricci Cantine Storiche, but you can stop into Cantina Contucci to just try the wines.

For dinner, I would try to snag a reservation for OSTERIA ACQUACHETA, one of the most popular restaurants for Florentine Steak. It’s hard to get a reservation, but worth it if you can. If you do have extra time before dinner, consider making the steep walk down to the Sanctuary of the Madonna di San Biagio (or drive by it before arriving in the village).

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Days 8-10: Florence

For your final days in Tuscany, make your way to Florence. The city is well worth spending 3 full days in, which is why I’ve created a detailed 3-day Florence itinerary to help you plan your days there. The itinerary includes everything from my extensive Florence travel guide and guide to Florence with young kids.

When it comes to exploring Florence, enjoy sights like Piazza della Repubblica, the Cathedral of Santa Maria del Fiore (the Duomo itself), and Brunelleschi’s Dome (Cupola del Brunelleschi). Book a Sunset Food & Wine Tour through Oltrarno, where you’ll taste some of Florence’s best food. Don’t miss a morning at Palazzo Pitti and Giardino di Boboli (Boboli Gardens) and nearby artisan shopping in the neighborhood.

All of this and more is in my detailed 3-day Florence itinerary. Below, I’ve included my quick list of places to stay in Florence. If you’re looking for a more detailed look at accommodations and neighborhoods in Florence, then read my where to stay in Florence guide.

My Top Picks for the Best Hotels in Florence:

1. Hotel Number Nine ($$$ / Where I Stayed), for the best boutique hotel with a spa and central location near San Lorenzo
2. Hotel Savoy ($$$), for the best luxury hotel in the heart of Florence’s historic center
3. The Artists’ Palace Florence ($$), for the best apartment-style suites near Piazza San Lorenzo
4. Plaza Hotel Lucchesi ($$$), or the best river-view hotel with a rooftop pool near Santa Croce
5. Bernini Palace ($$$ / Where I Stayed), for the best old-world luxury stay steps from Piazza della Signoria
6. Hotel Lungarno ($$$), for the best luxury hotel in Oltrarno with river views and a design focus
7. La Maison du Sage ($$), for the best refined boutique hotel in a quieter area near Santa Croce
8. Hotel Palazzo Guadagni ($$), for the best Oltrarno stay with rooftop views over Santo Spirito

My Top Picks for the Best Airbnbs in Florence:

1. 2 Bedroom Oltrarno Apartment with Panoramic Terrace, for the best rooftop views in Oltrarno with a terrace overlooking Santo Spirito
2. 1 Bedroom Penthouse with Terrace and Jacuzzi, for the best luxury rental on Via Tornabuoni with a private terrace
3. 1 Bedroom Historic Apartment in Santo Spirito, for the best character-filled Oltrarno stay with a frescoed bedroom and veranda

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