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Table of Content:

Introduction: Discover the Beauty of Tuscany
Your 5-day Itinerary at a Glance
Day 1 | San Gimignano, Pisa, Volterra
Day 2 | A Full day Exploring the Chianti Wine Region
Day 3 | Florence: Renaissance Art and the Magnificent Duomo
Day 4 | Montalcino, Bagno Vignoni, Pienza and Montepulciano
Day 5 | Discover Siena, then Relax at your Villa
Practical Tips for Planning your Tuscan Itinerary
References
The Wrap up

Pienza

1. Introduction: Discover the Beauty of Tuscany:

Everything you’ve pictured or imagined about Tuscany is true, rolling hills dotted with cypress trees, medieval towns perched on hilltops, vineyards stretching across the countryside and long lunches enjoyed in the Italian sunshine—Tuscany is the kind of place that makes you want to slow down and savour every moment.

With its rich history, beautiful architecture, world-renowned wines and charming villages, this region of central Italy offers something special from one end to the other, you really can’t go wrong no matter where you go or which town you choose. From the iconic sights of Florence and Pisa to the quieter beauty of Bagno Vignoni and Pienza, there is so much to discover beyond the main tourist attractions.

For our five-day itinerary, Siena was our home base, which allowed us to easily explore different parts of Tuscany while returning to the same accommodation each evening. Along the way, we visited medieval hilltop towns, spend a day exploring the vineyards of Chianti, discovered Florence’s Renaissance treasures, wander through the beautiful Val d’Orcia countryside and finish with time to enjoy Siena itself. We hope this Itinerary works for you as well as it did for us.

This itinerary is designed for travellers who love a well-planned day but still want time to wander, take photographs, enjoy a delicious meal and appreciate the little moments along the way.

So, pack your camera and get ready to discover five dreamy days in Tuscany!

2. Your 5-Day Tuscany Itinerary at a Glance:

Day 1: San Gimignano, Pisa and Volterra — medieval streets, iconic landmarks and ancient history.
Day 2: Chianti wine country — scenic drives, charming villages, vineyards and a winery tour with a tasting & picnic.
Day 3: Florence — Renaissance art, the magnificent Duomo and Michelangelo’s David.
Day 4: Montalcino, Bagno Vignoni, Pienza and Montepulciano — hilltop towns, thermal waters, local food and a Tuscan sunset.
Day 5: Siena and a relaxing afternoon at your villa — historic streets, beautiful architecture and time to unwind.

3. Day 1 | San Gimignano, Pisa and Volterra:

Your first day takes you to three very different Tuscan destinations. Start early in San Gimignano, visit the famous Leaning Tower of Pisa around lunchtime and finish the day exploring the historic hilltop town of Volterra.

This is one of the busier days in the itinerary, so an early start and a little flexibility will help you make the most of it. If you think this day looks too ambitious you could skip Pisa as it’s the furthest town and spend the morning in San Gimignano and the afternoon in Volterra. You know your comfort level so do what’s right for you.

Early Morning in San Gimignano

Leaning Tower of Pisa

Etruscan Arch in Volterra

Morning: San Gimignano –

Siena to San Gimignano – Approx. 45 mins (we arrived around 7:00am)

Leave Siena early and head to San Gimignano, a beautiful hilltop town known for its medieval towers, stone streets and historic architecture. Its distinctive skyline has earned it the nickname the “Manhattan of the Middle Ages,” and its historic centre is a UNESCO World Heritage Site. Arriving early allowed us to explore for a little while during the less crowded time.

Begin with some exploring, then breakfast at a café in the historic centre. Enjoy a coffee and pastry before the town becomes busier, then spend the morning wandering through its narrow lanes and picturesque squares.

Things to see and include:

Piazza della Cisterna: A beautiful triangular medieval square surrounded by historic buildings with a large well in the centre.
Piazza del Duomo: The heart of the old town, with its cathedral and medieval architecture.
Torre Grossa: If you’d like panoramic views, consider climbing the town’s tallest surviving tower.
The little side streets: Explore beyond the main squares, where you’ll find lovely architectural details, traditional shops and quieter corners.

San Gimignano is also known for Vernaccia di San Gimignano, its local white wine, and for traditional Tuscan food. If interested you could do a wine tasting at one of the wine shops in town.

Allow approximately three hours for breakfast and exploring before continuing to Pisa.

Midday: Pisa and the Leaning Tower –

San Gimignano to Pisa – Approx. 1-hour 15mins

Next, drive north to Pisa for lunch and a visit to one of Italy’s most recognizable landmarks.

Head to the magnificent Piazza dei Miracoli, or Square of Miracles, where the famous Leaning Tower of Pisa stands beside the cathedral and baptistery.

Admire the tower from the square, photograph its distinctive tilt and explore the surrounding architectural complex. If climbing the tower is on your wish list, reserve an entry time in advance, as access is limited.

For lunch, find a trattoria or café in or around the historic centre. This is a good opportunity to enjoy a relaxed Italian meal before continuing your journey.

After lunch, allow time for photographs and a stroll along the river. If you’re keen to explore inside the monuments, remember that doing so will reduce the time available in Volterra, so it will depend on your preferences.

Plan for approximately two to three hours in Pisa, including lunch.

Late Afernoon/Evening: Volterra –

Pisa to Volterra – Approx. 1 hour 20 mins

Your final stop is Volterra, a historic hilltop town with a quieter atmosphere and a fascinating Etruscan past.

Once you arrive, wander through its stone streets and explore the old town at your own pace. If you’re interested in history, look for the Etruscan Arch (Porta all’Arco), an ancient gateway that formed part of the city’s early fortifications. Its weathered stonework is a remarkable reminder of the civilization that flourished here long before the Renaissance.

Other highlights include the historic centre’s piazzas, traditional shops and viewpoints over the surrounding countryside. Volterra is also known for its alabaster craftsmanship, making it a lovely place to browse for a locally made keepsake.

Finish the evening with dinner in the historic centre. Choose a traditional Tuscan restaurant, order a regional dish and enjoy the slower pace before driving back to Siena.

A practical note: This is an ambitious day, with considerable driving between all three destinations and back to Siena. You won’t have time to see everything in each town. If you prefer a slower pace, give San Gimignano and Volterra more time and save Pisa for another visit.

4. Day 2 | A Full Day Exploring Chianti Wine Region:

After yesterday’s busy sightseeing, today is all about enjoying the countryside. The Chianti region, between Florence and Siena, is known for its rolling vineyards, olive groves, historic estates and villages surrounded by beautiful scenery.

This is the day to slow down, take the scenic route and enjoy one of Tuscany’s best-known traditions: wine.

Tuscan Views

Castello di Brolio

Fattoria di Montemaggio Winery

Morning: Explore the Chianti Countryside –

Leave Siena early and head north into Chianti. Start in Castellina in Chianti for breakfast and a little walk.

Siena to Castellina in Chianti – 30 mins

Part of the pleasure of exploring Chianti is the drive itself. Winding country roads lead past vineyards, olive groves, stone farmhouses and cypress trees, making this a wonderful area to enjoy at a leisurely pace.

A few Chianti Towns worth the stop:

Castellina in Chianti: A traditional hilltop town where you can wander through the old centre and discover its historic character.
Greve in Chianti: Known for its main square, local shops and connection to the region’s wine culture.
Radda in Chianti: A charming historic village with stone streets and lovely countryside surroundings.

Late Morning: Winery Tour, Tasting & Possible Picnic –

Castellina in Chianti to Wine Tour – 35 mins

One of the highlights of visiting Chianti is experiencing a winery firsthand. Book a guided tour and tasting at an estate that interests you, ideally one where you can learn about the winemaking process as well as sample the wines.

A typical experience may include a walk through the vineyards, a look at the cellar and an introduction to Chianti’s wine traditions, followed by a tasting.

Allow time for lunch, too. Some wineries offer food pairings, light meals or lunches, while others are close to villages with traditional trattorias. Check what’s included when you book so you can plan your day accordingly.

We did our tour at the Fattoria di Montemaggio winery and really enjoyed it, plus they offer a picnic lunch in their vineyard, which was a “pinch me moment”. Checkout this tour here.

A tip for booking: Reserve your winery tour in advance, (3 to 6 months) confirm the start time and check whether lunch is included. If you’re driving, choose your designated driver or alternative transportation so everyone can enjoy the experience responsibly.

Afternoon: Enjoy the Scenic Route –

After lunch and your tasting, leave room for a little more exploring. Stop at a viewpoint, browse a local shop or enjoy a coffee in a village square. You could visit Greve in Chianti or Radda in Chianti, we enjoyed our visit to Castello di Brolio, this is an impressive Castle with stunning Tuscan views. We weren’t able to go inside the castle, but we could explore the interior of the chapel, walk the grounds, and enjoy the views. The ticket we purchased at the entry also included a free glass of wine in town at the Enoteca del Castello di Brolio, all in all was a relaxing experience.

Return to Siena in the early evening. For dinner, you can choose a restaurant in the city or checkout the local grocery store and pick up items to make a charcuterie board meal and enjoy a quiet evening at your villa.

Castello di Brolio to Siena – 40 mins

My tip: Don’t overfill this day with winery reservations. One well-chosen tour, a village or two and time to enjoy the countryside will make for a much more memorable experience than rushing from stop to stop.

5. Day 3 | Florence: Renaissance Art and the Magnificent Duomo:

Florence deserves more than a quick stop, but if you have just one day, planning ahead will help you see some of its most famous landmarks without spending the entire day in queues.

Today, you’ll visit the cathedral complex and climb Brunelleschi’s dome, then see Michelangelo’s celebrated statue of David before exploring the city’s historic streets.

Palazzo Vecchio

The Duomo

Getting to Florence: Park at Villa Costanza

Siena to the Villa Costanza Park-and-Ride – 1 hour

Rather than driving into central Florence, use Villa Costanza, the park-and-ride facility connected to Florence’s tram network.

The parking area is directly linked to tram line T1, which takes approximately 20–25 minutes to reach the Santa Maria Novella station in the city centre. Check current tram schedules and fares before travelling here.

This is a convenient way to avoid the challenges of driving and parking in Florence’s restricted-traffic historic centre.

Morning: Florence Cathedral and the Dome Climb –

Begin at the Cathedral of Santa Maria del Fiore, usually known as the Duomo. Its enormous dome, colourful marble exterior and impressive scale make it one of Florence’s defining landmarks.

If you want to climb Brunelleschi’s dome, book your timed entry well in advance (3 to 6 months beforehand). The climb involves a substantial number of stairs and can feel narrow in places, but it rewards visitors with close-up views of the dome’s interior and wonderful panoramas over Florence.

The cathedral itself generally offers free admission, while the dome and other monuments require the appropriate ticket. The Brunelleschi Pass includes access to the dome, bell tower, baptistery, museum and Santa Reparata, with a reserved time slot required for the dome climb. Check the official Opera di Santa Maria del Fiore website for current ticket details and access conditions here. This is the pass we got and it worked well.

Allow time to admire the cathedral’s exterior and surrounding Piazza del Duomo, even if you have a timed reservation.

Lunch: Enjoy a Florentine Break –

After your cathedral visit, find a café or trattoria in the historic centre. Florence is known for Tuscan favourites such as ribollita, pappardelle with ragù and the famous bistecca alla fiorentina.

Choose somewhere that suits your appetite and budget and give yourself a little time to rest before the afternoon’s sightseeing.

Afternoon: See Michelangelo’s David –

Next, head to the Galleria dell’Accademia, home to Michelangelo’s extraordinary marble sculpture, David.

Seeing the statue in person is a memorable experience. Its scale, intricate details and lifelike presence are difficult to appreciate fully in photographs.

Book your Accademia Gallery admission in advance as well, choosing a time that works with your dome reservation and lunch. The museum is popular, and advance booking usually comes with a skip-the-line which can help you avoid long waits. These are the tickets we got for the dell’Accademia here.

Once you’ve seen David, take a leisurely walk through Florence’s historic centre. Visit Piazza della Signoria, admire the Ponte Vecchio, cross the Arno River and checkout the Pitti Palace, walk along the river, and simply wander the surrounding streets and photograph the beautiful architecture.

Evening: Return to Siena –

After a full day in Florence, take the tram back to Villa Costanza and drive back to Siena. Keep dinner simple if you’re tired or choose a restaurant in Siena’s historic centre if you still feel like exploring.

My tip: Don’t try to squeeze every famous Florence landmark into this one day. Your two priority bookings—the dome climb and the Accademia Gallery—should shape the schedule. Enjoy the remaining sights as time allows.

Checkout our 5-Part Travel Series on Florence for more information on this romantic city. Here!

We loved Florence so much so, we went back a second time.

6. Day 4 | Montalcino, Bagno Vignoni, Pienza and Montepulciano:

If you love the quintessential Tuscan landscape of rolling hills, cypress-lined roads, vineyards and medieval villages, this may be your favourite day of the trip.

The Val d’Orcia lies south of Siena and is recognized as a UNESCO World Heritage cultural landscape. Its scenery reflects centuries of agricultural life, with hilltop towns and winding roads creating some of Tuscany’s most memorable views.

Montalcino

Bagno Vignoni

Pienza

Sunset in Montepulciano

Early Morning: Montalcino –

Siena to Montalcino – 50 mins

Start early and drive to Montalcino, a hilltop town surrounded by vineyards and famous for Brunello di Montalcino wine.

An early visit is ideal for enjoying the town’s streets before the day becomes busy. Walk through the historic centre, admire the stone buildings and make your way to the medieval fortress for views over the surrounding countryside.

Montalcino is especially associated with red wine, so you may want to browse local wine shops, and do a tasting. Keep in mind today’s schedule includes several stops, so while you don’t have to rush, you want to divide your time between these amazing towns.

If you arrive very early, remember that cafés and shops may not yet be open, so you can do a bit of exploring before breakfast.

Late Morning: Bagno Vignoni –

Montalcino to Bagno Vignoni – 25 mins

Continue to Bagno Vignoni, one of Tuscany’s most unusual little villages.

At its centre is Piazza delle Sorgenti, a large pool of thermal water surrounded by historic stone buildings. Unlike a typical Italian village square, the central feature here is the water itself, reflecting the village’s long connection with natural hot springs.

Take a walk around the square, explore the little lanes and enjoy the peaceful atmosphere. It is a small village, so you won’t need hours to see the main sights, but it’s worth taking your time and appreciating its unique character.

Please note that the historic central pool is not a swimming pool. If you’re interested in bathing in thermal water, check the options and access rules at local facilities before your visit.

Lunch: Pienza –

Bagno Vignoni to Pienza – 20 mins

Next, make your way to Pienza, a beautiful Renaissance town overlooking the Val d’Orcia and one of our very favourites.

Pienza is known for its harmonious architecture, charming lanes, panoramic viewpoints and local pecorino cheese. Its central Piazza Pio II brings together the cathedral and historic palaces in a carefully planned Renaissance setting. We especially loved photographing the doors and windows here.

This is the perfect place to stop for lunch. Look for a trattoria serving Tuscan dishes, or enjoy a lighter meal with local pecorino, bread and other regional specialities.

After lunch, spend some time wandering the streets, browsing the food shops and stopping at the viewpoints along the town’s edge. The views over the surrounding hills are a highlight, so keep your camera handy.

Late Afternoon and Evening: Montepulciano –

Pienza to Montepulciano – 25 mins

Finish the day in Montepulciano, another beautiful hilltop town with steep streets, Renaissance architecture and sweeping views across the countryside.

Make your way through the historic centre towards Piazza Grande, the town’s main square, and take time to admire the historic palaces and cathedral. Montepulciano is also famous for Vino Nobile di Montepulciano, making it another wonderful destination for wine lovers.

As evening approaches, grab a glass of wine and find a spot to watch the beautiful Tuscan sunset, then find a restaurant for dinner. Choose a table where you can enjoy a leisurely meal before taking one last stroll through the town.

A note on timing: Four destinations make for a full day. If you want a long lunch, a winery visit or more time browsing shops, you’ll need to trim one of the other stops. Check sunset time for your travel dates and plan the final part of the day around it. Check those our here.

Montepulciano to Siena – 1 hour

7. Day 5 | Discover Siena, Then Relax at Your Villa:

After four busy days of sightseeing and driving, today is designed to be slower. Spend the morning discovering Siena’s historic centre, enjoy a leisurely lunch and then return to your villa for a relaxing afternoon.

Piazza del Campo in Siena

Views from our Villa

Morning: Explore Siena’s Historic Centre –

Begin with a walk through Siena, a medieval city with beautiful brick buildings, winding streets and an impressive artistic heritage.

Start at Piazza del Campo, Siena’s distinctive shell-shaped main square. Surrounded by historic buildings and the Palazzo Pubblico, it’s the heart of the city and the setting for the famous Palio horse race, held twice each summer.

From there, wander through the surrounding streets and make your way to the Siena Cathedral, known for its striking black-and-white marble and richly decorated interior. If you have time and enjoy exploring historic churches, consider visiting inside to appreciate its artwork and architectural details.

Leave time to browse the small shops, stop for a coffee and enjoy the architecture. Siena is a wonderful city to explore on foot, and some of the best moments come from turning down a side street simply because it looks interesting.

Lunch: Enjoy One Last Tuscan Meal

Choose a trattoria in the historic centre, perhaps with a view and enjoy a relaxed lunch before heading back to your accommodation. This is a lovely opportunity to try a regional favourite you haven’t yet sampled, whether that’s handmade pasta, a hearty soup or another traditional Tuscan dish.

There’s no need to rush through lunch today. Enjoy the food, soak up the atmosphere and reflect on all the beautiful places you’ve explored over the past few days.

Afternoon: Relax at Your Villa –

One of the pleasures of staying in a villa is having somewhere to return to and enjoy beyond simply sleeping there.

After several days of sightseeing, give yourself permission to slow down. Sit outside with a coffee or glass of local wine, read a book, enjoy the countryside views or simply relax without having to watch the clock.

If your villa has a garden, terrace or pool, make the most of it. You could also pick up a few local ingredients and enjoy a simple dinner at home.

Sometimes the most memorable part of a trip isn’t another attraction—it’s having the time to enjoy where you are.

Balcony in Pienza

8. Practical Tips for Planning Your Tuscany Itinerary:

A little planning makes a big difference in Tuscany, especially when you’re combining several towns and a day in Florence.

Getting Around –

Rent a car for the countryside. A car gives you the flexibility to visit the hilltop towns, vineyards and scenic viewpoints in this itinerary.
Use Villa Costanza for Florence. Park there and take the tram into the city instead of driving into the historic centre, (make sure you validate you ticket on the tram).
Check driving times before you leave. The route between towns can take longer than expected, particularly on winding country roads. Allow extra time for parking and walking into historic centres.
Be aware of ZTL zones. Many Italian historic centres have restricted-traffic zones. Check parking locations and access rules before driving into any town.

Always park outside any of the old towns, we research the parking lots before leaving so we can put the actual parking lot into our GPS, it makes things much less stressful.

Booking Attractions and Experiences –

Reserve the Florence Duomo climb early. Choose a timed entry for Brunelleschi’s dome and allow enough time to get there.
Book the Accademia Gallery in advance. This is especially important if seeing Michelangelo’s David is a priority.
Reserve your winery visit. Confirm the tour, tasting, language and any food included before travelling to the estate.
Check opening days and hours. Churches, museums, shops and restaurants can have different schedules depending on the season and day of the week.

Make the Most of Your Days –

Start early for popular towns. San Gimignano and other well-known destinations are more peaceful earlier in the day.
Leave room for photographs. Tuscany’s countryside is full of beautiful viewpoints but stop only where parking is safe and permitted.
Don’t try to see everything. This itinerary is full, particularly Days 1 and 4. Treat it as a guide rather than a race. This is our actual Itinerary we used and it did worked well for us, but if you think it might be too rushed, you can always decide the day of and leave one town out, for example on day 1 if seeing the leaning tower of Pisa isn’t overly important to you, spend a half-day in San Gimignano and a half-day in Volterra.
Plan wine tastings responsibly. If you’re driving, arrange a designated driver or alternative transportation.
Pack comfortable walking shoes. Cobblestones, steep lanes and stairs are common in historic Tuscan towns.
Check sunrise and sunset times before you go, especially to help you plan where you want to see the sunset with a glass of wine. Check them out here.

Plan. Travel. Capture.

9. References:

For our Tuscan Travel Series, we created our top towns & wine region, itinerary, and tips and recommendations from our own experiences we had while visiting this stunning & romantic part of the country. As well, we read helpful travel books like, Eyewitness Travel Italy, Eyewitness Top 10 Florence & Tuscany, Rick Steves Itlay, Rick Steves Florence & Tuscany and Rick Steves Hill Towns of Central Italy, which helped shape our adventure. In addition, we like to explore the official tourism websites, (visittuscany.com/en) attraction sites, public transportation resources (like buses, ferries, and trains), and a few local food blogs to see what local foods piques our interest. Google Maps for driving and walking distances, travel apps like OMIO for train travel and tour apps for any activities, like Get Your Guide, Viator or Expedia. We hope you find this Itinerary helpful when planning your own adventure to this breathtaking region.

Views from Montepulciano

10. The Wrap Up:

Tuscany has a way of making even the simplest moments feel special. From wandering the medieval streets of San Gimignano and admiring the Leaning Tower of Pisa to tasting wine among the Chianti vineyards and watching the evening light fall over Montepulciano, each day brings something different.

Basing yourself in Siena lets you experience several sides of the region, from its most famous landmarks to quieter villages and beautiful countryside. The itinerary is ambitious, but with a little advance planning—and a willingness to adjust the pace when needed—you can enjoy a wonderful introduction to Tuscany.

And don’t forget to leave a little time for the moments that aren’t on the itinerary: a coffee in a sunny piazza, a photograph of a winding country road or an unhurried afternoon at your villa.

Because sometimes, the best way to experience Tuscany is simply to slow down and relaxing in your surroundings.

Planning a trip to this destination?

Plan Better. Travel Deeper. Capture More.

Thank you,

Beth

Beth de Verteuil

Wild Meadow Studio

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