How to Plan an Incredible 7 Day Tuscany Itinerary

Disclaimer: Some of the links in this post, like hotel links, are affiliate links, meaning at no additional cost to you, we make a little bit of money if you click through and book. That being said, we would never recommend something to you that we don’t stand behind 100%.

A Quick Tuscany Geography Overview

Before delving into the specifics of the Tuscany itinerary, it makes sense to briefly discuss the geography of Italy’s most famous region.

Tuscany is in central Italy and is a land of olive trees as far as the eye can see, rolling slopes, winding paths, and cypress trees.

The capital of Tuscany is Florence, worth a couple days exploring (recommendation to do at trip end), but cities like Pisa and Siena also within Tuscany’s boundaries.

To discuss what to focus your time on when you visit Tuscany, we’re going to separate the region into four distinct areas. This is just our way of breaking things down into more understandable pieces, it’s not an official designation or anything like that.

Here are those four regions: 

• Florence & Around (including Chianti)
• Siena & Around
• The rural regions of southern Tuscany including Pienza and Montepulciano in the Val d’Orcia valley
• San Gimignano and Volterra

Other regions in Tuscany – like Pisa and Lucca further north, and the Tuscan coast stretching to the west – have attractions as well, but if time is limited and you seek the quintessential countryside setting, focus your 10 days or less on these four locales (applicable for most readers).

With that brief and incomplete overview provided, let’s delve into the key details required to actually plan your Tuscany road trip.

Do You Need a Car for This Tuscany Itinerary?

.

”

You’ll need to rent a vehicle, and we’d strongly recommend you avoid having a car for your time in Florence (if you decide to include the biggest city in Tuscany in your itinerary). Parking in Florence will be expensive and unnecessary – you really don’t need a vehicle.

To make this work, we would place Florence at the conclusion of your Tuscan travels.

You’ll want to rent a car from the airport when you arrive and head straight down to Siena, and then drop it off on the day you RETURN back in Florence (day 6, if you follow our itinerary below).

Then take the bus from the Florence Airport into the city, and spend a couple of days exploring before heading home!

That way, you don’t have to deal with traffic or parking in Florence, which can be a nightmare.

Here are a few things to know about renting a vehicle in Italy (keeping in mind that we’re American).

You Need an International Drivers License if You’re Coming From the US

Motorists can obtain them at AAA in the USA. While rental car staff may not ask for it at the counter, law enforcement will request to see it if one experiences an accident or gets pulled over. It`s best not to chance being without it.

Know Your Toll Roads

Roads requiring payment in Italy – called Autostrade – essentially serve a comparable purpose to Interstate highways within the United States.

They have anywhere from two to four lanes, high velocity limits, and are more or less a direct route between destinations. You can only enter and depart them at fixed points, but there are gas stations and casual restaurants at rest stops along the way.

Unlike here in the US, you must pay to use the highways, which are toll roads.

This is accomplished either by renting a transponder from the vehicle rental company, or by stopping at one of the entrance stations and obtaining a ticket, which is paid upon exit from the toll road. Credit cards are nearly always accepted nowadays based on experience.

Here’s a guide to help you understand road toll systems in Italy.

What If You Don’t Want to Drive in Tuscany?

Look, we completely understand the hesitation to drive in a foreign nation. Especially in a country like Italy, which doesn`t precisely have a reputation for hosting friendly, patient motorists.

If you don’t want to drive in Italy (or can’t drive in Italy), you can still make this itinerary work using a mix of public transportation and guided excursions.

You’ll want to base yourself in Florence and Siena – which are connected by train and bus, so they’re relatively easy to get between – and use them as a central location to do day trips out into the wider Tuscan countryside.

Sadly, that implies you’re going to pay more for guided trips to the Val d’Orcia and San Gimignano, and you’ll have less flexibility to freely explore without a vehicle.

Where to Start and End Your Tuscany Road Trip

Without a doubt, the best place to begin and conclude this road trip will be Florence. There are three main reasons we think that’s the case.

To start, if you’re flying in from outside of Italy, Florence offers the best choice in terms of finding flights. You’ll want to fly into the Florence Airport (FLR), NOT PISA INTERNATIONAL AIRPORT, which as one might assume, is actually situated in Pisa (about 45 minutes west of Florence).

Second, you’ll have the best selection of rental vehicles in Florence.

Thirdly, Florence is the closest significant urban center (with a reliable airport) to the main areas of Tuscany we discussed previously. It will take approximately one hour and 15 minutes to travel from Florence to Siena, your first destination on this Tuscany itinerary.

Another airport worthy of consideration – and this is actually the airport we flew into – is Bologna Guglielmo Marconi Airport (BLQ). It lies approximately 45 minutes north of Florence (meaning the travel time to Siena would be around 2 hours), but it presents a good alternative and you may be able to find somewhat cheaper rental cars and flights there.

Additionally, we are quite fond of Bologna, and recommend dedicating a day or two to exploring all it has to offer (check out our guide to spending one day in Bologna).

Plan on carrying out a sizable circular route throughout the region of Tuscany, and returning your mode of transportation to the identical airport from which you arrived (and flying back from, if applicable).

Is One Week in Tuscany Enough Time?

Spending just a couple days in Tuscany does not allow sufficient time to truly immerse yourself in and appreciate the region`s renowned slow-paced lifestyle and culture.

We think a week is the minimum timeframe needed to experience all four regions of Tuscany discussed above.

That duration will give you enough time to delve beneath superficial examinations of each location. That is why we chose to structure this guide around a 7 day exploration of Tuscany.

A good example of why this is important is Siena. Siena is extremely busy during the day when buses full of tourists get dropped off to wander through Piazza del Campo and the Duomo.

However, when those tour buses leave, Siena transforms into a much more peaceful destination – the narrow alleyways go from packed wall-to-wall with people to being nearly deserted.

For a two day visit to Tuscany, one won`t have time to experience Siena during early morning or evening hours when an altogether different and more comfortable atmosphere exists.

What should you do if you only have 3-5 days or so? Focus on one or two of the regions above rather than trying to experience everything.

We provide suggestions below for planning shorter versions of the itinerary, including 3- and 5-day options focused on Tuscany.

More time? Great! We also have suggestions on what to do with your extra time in a section below the main itinerary.

Where to Stay for Your Tuscany Road Trip

When deciding where to lodge, there are essentially three approaches one could take: reside in one place for the entire trip, and use it as a base for exploring the entire region, stay in a different place each night, or find a home base in each micro-region and stay there for a couple of nights each.

As you might expect, we prefer the last approach, which combines the benefits of staying in each part of Tuscany you visit (reducing drive time) without needing to move locations every night.

If you follow our itinerary below as written, you’ll stay in Florence, Siena, and the Val d’Orcia region for 2-3 nights each.

Additionally, we have prepared an extensive guide focused on assisting you in identifying the perfect accommodations in Tuscany. For more details, please refer to that guide.

Hotels in the City Center vs. Agriturismos?

The next decision you’ll need to make is what type of accommodation you’re looking for. Do you want to stay right in the center of all the activity in a hotel in the city center, or would you rather have a tranquil stay in the Tuscan countryside?

Our (strong) inclination is the latter – we solely lodged at Agriturismos in Tuscany, and loved each moment there.

You won’t need to worry about (or pay for) overnight parking, you’ll have a little more space (if you’re fortunate, a patio with some nice views), and you’ll be immersed in the warm atmosphere as you sip your morning coffee on the outdoor patio with a view of Cypress Trees and hilltop towns.

The upside of staying in the center of a city is, obviously, convenience. However, parking and navigating ZTL (the car-free zones in the city center of most of Tuscany’s towns and cities) make staying in a city with a car less appealing, at least in our estimation.

Our recommendation would be to spend your two nights in Florence in the city center (you won’t have a vehicle at this point, so parking isn’t as much of an issue), and stay in the countryside surrounding Siena and in the Val d’Orcia.

Where to Stay in Florence, Siena, and the Val d’Orcia

Let us briefly outline some recommended accommodation options based on our experience and research.

In Siena, we stayed at Il Palazzetto just outside of town for a few nights and enjoyed having our morning coffee with a scenic view of Tuscany from our front porch.

The accommodation is a farmhouse surrounded by olive trees, rolling hills, and Cypress trees in the countryside. They have several beautiful rooms and apartments on the property. The staff were very friendly and helpful in providing recommendations for sights, activities, and dining in Siena.

In the Val d’Orcia, we stayed at Agriturismo Il Casalino, a cute little farmhouse in the valley below Pienza with a spectacular perspective of Pienza up on the hill. Very friendly owner, and the location is truly excellent. Cypress trees and rolling hills as far as the eye can see!

In Florence, you’ll want to stay in the city center. We stayed at Pietrapiana Boutique Apartments, which are in a superb central location around ten minutes from the Duomo di Firenze. They’re compact, but they provide a little more space to unwind and relax.

Here’s our guide to where to reside in Florence for more detail.

7 Days in Tuscany: How to Plan an Amazing Tuscany Road Trip Itinerary

With a week in Tuscany, we strongly advise restricting your trip to Florence, Siena, the Val d’Orcia, and San Gimignano (plus a side trip to Volterra) to prevent driving for hours daily and, most significantly, missing out on the relaxed lifestyle that makes this part of Italy unique.

We`ve organized this itinerary as a loop starting and finishing in Florence, as mentioned earlier.

Now, here is the schedule for the trip day-by-day. The itinerary includes a map to help visualize the route.”

• Day 1: Siena
• Day 2: Siena
• Day 3: Val d’Orcia
• Day 4: Val d’Orcia
• Day 5: San Gimignano and Volterra (conclude in Florence)
• Day 6: Florence
• Day 7: Florence

Now that you’ve got a good outline of the geography and logistics, let’s get into precisely how to spend one week in Tuscany!

Either way, bypass Florence for now (you’ll return!) and head straight down to Siena, which should take you around 90 minutes, depending on traffic flow.

Nowhere can one truly immerse themselves in Tuscany`s medieval heritage quite like the mountaintop town of Siena, one of Italy`s most pristinely preserved medieval villages.

The striking city is characterized by its reddish-brown brick houses, grand Gothic sanctuaries and palaces, and soaring medieval towers. It’s home to some of the finest artistic and architectural works in the country thanks to its great wealth and influence during the 13th and 14th centuries.

Siena is also renowned for its historic equine race, which occurs on July 2nd and August 16th each year. The event has been happening within the city since the 15th century and highlights 10 riders from various districts racing bareback around central Piazza del Campo.

This is one of the most energizing – albeit extremely busy and pricey – times to visit.

Things to Do in Siena

Siena’s one-of-a-kind medieval architecture and distinctive charm have gained the city recognition as a UNESCO World Heritage Site. And it is now one of Tuscany’s most popular destinations.

This does mean, however, that it becomes rather busy throughout the year, with crowds comparable to even larger cities like Florence and Pisa.

There is an implication of Siena`s popularity that you ought to take into account.

Numerous visitors see Siena on a day outing from Florence, meaning it’s at its busiest in the middle of the day.

To experience the city at its most peaceful time, head out early in the morning or late in the evening and enjoy having space on your own. This is why we’ve suggested spending two days in Siena.

• A curated stroll through Siena. We participated in this guided walk on our first day and it expertly introduced us to the history and lifestyle of Siena. The excursion even included entry to the cathedral, a fascinating place to explore with a knowledgeable ambassador who points out subtleties you otherwise may overlook (though admission to the cathedral viewpoint is separate – more below).

• Piazza Del Campo. Siena’s impressive main square is encompassed by stunning Medieval palaces and historic buildings. Today, it’s a hub of social life in the city and a great place to take a stroll or stop for a beverage on the terrace of one of the charming cafes.

• The historic Duomo di Siena temple (and the vistas from Facciatone). Siena`s 13th century cathedral is considered one of the finest Gothic religious structures across Italy, featuring an intricate marble facade and lavishly decorated interiors adorned with intricate details. Visitors are particularly struck by the vibrant stained glass windows and amazing mosaic floors. Additionally, the panoramic views from the top of the incomplete church expansion at the now museum, known as Panorama dal Facciatone, provide a breathtaking overlook of the historic city below. While requiring a special ticket, accessing this viewpoint is worth the extra cost in our opinion.

• Partaking in Food and Drink in Siena. Siena offers a bounty of delicious culinary experiences. Establishments we’d advise trying for eating and drinking in Siena include Bakery Il Magnifico (renowned for Siena’s signature chewy almond cookies), Caffetteria Torrefazione Fiorella (for coffee at the counter), Du’ Cose Da Berna (advised by our agriturismo host), and La Prosciutteria Crudi e Bollicine Siena (for cured meats).

If you’re like us, the iconic pictures that popular culture strongly associates with Tuscany are rolling verdant hills, solitary cypress trees standing tall, and full-bodied red wines. Which, giving a preview, is exactly what you will discover in Tuscany (along with other gems as well).

The journey from Siena to the Val d’Orcia can take anywhere between one hour and one hour and 15 minutes, relying on the route and traffic flow.

The Val d’Orcia is quintessential Tuscany, with rolling green hills (at least in the spring and early summer before they turn brown) dotted with cypress trees used for farming, historic farmhouses, and picturesque hilltop towns.

The picturesque landscapes and unmatched natural beauty of the valley inspired numerous Renaissance artists during the 15th and 16th centuries to create paintings capturing what they saw.

Two days provides a good amount of time to take a brief road trip around the Val d’Orcia area. We’d suggest focusing your visit on the three primary towns of Montepulciano, Montalcino, and Pienza.

Things to Do in the Val d’Orcia

Pienza is located centrally between the two other towns. We’d recommend starting at Montepulciano or Montalcino on your first day and moving east or west with Pienza as the second stop to minimize travel time.

Many great lodging options exist in and around Pienza (for reference, we selected Agriturismo Il Casalino and were pleased) so it serves as a good home base in the region.

Another important note is that each town occupies a small space, so you’ll only need a couple hours to explore the town itself. You can spend the rest of your time savoring a leisurely lunch, drinking local wine with scenic views, and touring the winding countryside roads.

Montepulciano

This small community sits on the edge of a volcanic rock cliff face with far-reaching views over the surrounding valley.

Be sure to partake in wine tasting at De’ Ricci (Vino Nobile is the local red wine), climb the tower of Comune di Montepulciano for superb views of the valley unfolding to the west, and take a stroll along the winding Via di Gracciano nel Corso, the main street in town.

Montalcino

Situated at the heart of Tuscany’s renowned Brunello wine growing region, Montalcino is a must-see destination for red wine aficionados.

You can sample local Brunello wine at Ciacci Piccolomini D’Aragona (or any of the other vineyards south of Montalcino) where we gained a primer in Brunello, which is mainly made with the same grape varieties as Chianti, but is processed differently.

Exploring the well-preserved walls of the Fortezza di Montalcino citadel, the town`s medieval stronghold, as well as visiting the Romanesque Abbey of Sant`Antimo church next to the recommended winery, make for fascinating stops within the town`s history.

Pienza

A city from the Renaissance period renowned for its stunning panoramic perspectives of the landscape surrounding it. This viewpoint was our favored perspective.

The village also made its mark producing Pienza`s renowned Pecorino di Pienza cheese, which you can sample at La Taverna del Pecorino (try it baked with honey topping if available – pecorino con miele).

Also, don`t miss coffee with a view at the lovely Bar il Casello.

Both towns sit at the western end of Tuscany near the ocean. They are situated around 30km from each other and could take anywhere from 40 minutes to 1 hour to drive between. So be certain to factor this into your day if you do want to visit both locations.

San Gimignano is a lovely medieval town and another of Tuscany’s heritage sites designated by UNESCO. The small town once had over 70 soaring medieval towers shaping its skyline, earning it the exceptional title of the “Manhattan of the Middle Ages”.

Today just a handful of these towers still stand, but the town remains known as Italy’s “City of Towers”.

Nearby Volterra is marginally less renowned than its famous neighbor (unless you`re a Twilight fan, in which case you likely know it).

The less visited walled hilltop town is still a great place to explore and is worth the effort, with several historically and archaeologically important sites including a world-renowned Etruscan museum and a couple of Roman archaeological locations.

You’ll additionally discover notably smaller groups than San Gimignano, so it’s an ideal spot to escape the chaos for a couple of hours.

Things to Do in San Gimignano

San Gimignano is a relatively small town, and it is one of the most visited places in Tuscany.

Wandering the narrow roadways, you’ll likely find yourself packed tightly with other visitors if you’re there in the summer months between 11:00 am and 5:00 pm (particularly on a weekend).

However, it’s understandable why numerous visitors flock here – the towers of San Gimignano are an iconic aspect of Tuscany’s landscape.

• Having lunch in San Gimignano. San Gimignano is a lovely place to make the most of Tuscany’s world-class cuisine. Enjoy a meal on the terrace at Le Vecchie Mura for excellent food and scenic views. And don’t forget to grab some tasty gelato from Gelateria Dondoli (they also have gelato making classes).

• Drink Vernaccia Di San Gimignano. Produced in the vineyards surrounding the town, Vernaccia is Tuscany’s most renowned white wine. You can sample Vernaccia in most eateries and bars around town, or head to the Vernaccia di San Gimignano Wine Experience to learn more.

• Ascend the Torre Grossa. The bell tower of the Palazzo Communale (town hall) is the tallest remaining tower in San Gimignano, measuring approximately 54 meters high. You can climb approximately 66 meters of steps to reach the tower’s summit and enjoy beautiful views over the town. While there, spend 15 minutes admiring the artwork in the attached Palazzo Comunale – though not extensive, it is certainly worth a brief visit.

• Parco della Rocca park. This pleasant hilly area is the highest point in San Gimignano and is home to the ruins of a medieval stronghold. Today it’s a nice spot to take a stroll or stop for a relaxing picnic with amazing views over the town (the best perspective is from here).

Things to Do in Volterra

Also situated atop rocky high ground, the small town of Volterra possesses stunning panoramic perspectives of Tuscany, and even the sea on clear days.

There’s not a lot going on in town, and we found it to be pretty inactive on a random weekday afternoon in mid-October.

However, it’s gorgeous and is an important piece of history on the Italian Peninsula. It’s worth visiting for the walking tour and Etruscan Museum alone.

An afternoon in Volterra is well worth the drive from San Gimignano, in our view. You only need about half a day to see the highlights. Here are some of our favorite things to do in Volterra.

• The Museum of Etruscan Civilization. Volterra has been home to shifting inhabitants throughout history (continuously populated since the 8th century B.C.), including the Etruscans, who left impressions on the city. The museum of Etruscan artifacts within boasts one of the most extensive collections globally, worthy of several hours` examination.

• Strolling Tour.This twilight walking tour of Volterra (NOT THAT TWILIGHT) was one of our most beloved encounters all through Tuscany. It protected the history of the city in only one hour. The period of the tour fluctuates every day, and it is well worth the small donation (solely money) to hear about Volterra’s history from a local person, like the deed of sparing the primary entrance into town from destruction amid World War 2.

• Roman Ruins. One of the other intriguing elements featured here pertains to another group residing in the town over numerous years, the Romans. Archaeological excavations throughout the town have uncovered extensive Roman foundations in several locations, with the most notable example being the Roman Theater situated on the northern side of town ( here). There is one other, more freshly disclosed Roman amphitheater further north beyond the town, which was uncovered in the 2000s.”

As one of the richest and most powerful cities in all of Europe, if not the world, during the 15th century, it explains the unmatched elegance and grandeur still evident today.

Known as the ‘Birthplace of Renaissance’, Florence is a center of world-class art and architecture.

Its two impressive art galleries are home to more masterworks than you can possibly fathom, while the city itself is one giant open-air museum, with exquisite churches and grand Renaissance palaces on every corner.

It’s difficult not to become enamored with Florence, regardless of the huge volumes of visitors who descend on the Italian city throughout the entire year.

Things to Do in Florence

Florence, despite its small size compared to other Italian cities, still has plenty to see and do.

Two days provides sufficient time to experience the top attractions and visit the primary galleries.

However, try to avoid visiting the Uffizi Gallery and Galleria dell’Accademia on the same day. Even for the most avid art aficionado, it’s simply too much data to absorb all at one time.

• Piazza del Duomo & Ascending the Dome. Situated at the heart of the city, Piazza del Duomo is home to several important landmarks, including the 13th century Cathedral and its renowned dome, the Baptistery, and Giotto’s Bell Tower. With only two days, we’d prioritize seeing Brunelleschi’s Dome up close. By climbing the 463 steps to reach the top of the iconic structure, you can admire the striking frescoes and take in amazing views over the interior and surrounding area. Aim to do so in the morning for fewer visitors, and book ahead here.

• The Uffizi Gallery. This world renowned collection of artworks from the Renaissance and European periods contains approximately one hundred rooms of exhibits. Many of the pieces were brought together by the powerful Medici family over centuries between the 15th to 18th centuries. We would strongly advise taking a guided tour to add context and substance to your visit – it can otherwise feel overwhelming. We did this tour and found our experience to be truly exceptional!”

• The Gallery of the Academy and Michelangelo’s David. One of Florence’s major galleries is widely known for a specific artwork, Michelangelo’s statue of David, which is among the most famous sculptures globally. It’s worth exploring the gallery on a guided tour ( the tour I did) to learn more about the iconic statue and other pieces in the collection.

• Explore Oltrarno. Located across Ponte Vecchio on the opposite bank of the Arno River flowing through Florence`s historic center is the neighborhood of Oltrarno, one of our favorite areas of the city. Full of charming little piazzas, traditional eateries, and cozy bars, it`s a wonderful place for a leisurely stroll or afternoon drink. Check out Le Volpi e l’Uva for an excellent selection of Italian wines, and Gelateria Della Passera for what Alysha considers the finest gelato in Florence.

• Indulging in delightful cuisine offerings in Florence. The Tuscan region is renowned for its wonderful cuisine, and one can sample some of the finest examples in its capital city of Florence. Begin mornings savoring coffee from Coffee Mantra, delight in savory pizza from award-winning Ciro and Sons, and be sure to try the Pappardelle al Cinghiale (pasta and wild boar sauce) at Da Garibardi. The city also hosts two noteworthy food markets, Centrale and Sant’Ambrogio, which are must-visits for food aficionados.

More Than a Week in Tuscany? Here’s What We’d Add to Your Itinerary

The two places that were really enjoyed by many but missed if strictly following the above Tuscany itinerary as written are Chianti and Lucca, which are located west of most of this route.

With a few extra days, spending one or two days in each place would be advised. Both areas can certainly be covered in a single day respectively, but allocating two days affords the opportunity to explore at a more leisurely pace. You can absolutely experience Chianti as a half day excursion, either from Siena or Florence.

You`ll notice that we haven`t included Pisa here, which is in the same vicinity as Lucca. We much prefer Lucca to Pisa, both because Lucca offers a more interesting city experience overall, and because Pisa sees considerably more tourists.

If you absolutely must see the leaning tower of Pisa, then we’d add it as a day trip from Lucca (but we wouldn’t stay the night in Pisa, if avoidance can be achieved).

One must-do activity when visiting Lucca is climbing one of the various towers located in the city center, as the walled town is situated in a narrow valley encircled by mountains.

We climbed the Torre Guinigi, and the view from the top with the towers and churches of Lucca and the surrounding hilly landscape was sublime.

Another thing not to miss is Piazza dell’Anfiteatro, which is a piazza built on the site of an ancient Roman amphitheater. The piazza retains the same oval shape today, though the restaurants on it leave something to be desired.

Chianti Classico, similar to other notable Italian D.O.C.G. wines like Prosecco and Brunello, is a red wine crafted in a distinctive way primarily from Sangiovese grapes grown in the Chianti region.

It is one of Tuscany`s most renowned wines. If you don’t enjoy red wine, I have some unfortunate news for you – Tuscany is all about the red wines (except for vernaccia, a white wine originating from San Gimignano!).

As one might imagine, Chianti is all about tasting the wine. Now, on the itinerary above, you’ve covered a few different famous red wines from Tuscany like Brunello and Rosso di Montepulciano, and Chianti is somewhere in between the two in terms of prestige and cost.

The optimal way to experience the wines of Chianti is through a wine tour. In terms of guided excursions, there are two possibilities. You can either opt for a tour concentrating deeply on a single winery, usually covering a cellar visit and thorough tasting (but you’ll need to travel out to the winery yourself), or a tour taking you around numerous wineries.

Since you will have use of an automobile, we would propose the initial option, which offers a deeper, more intimate encounter. We participated in this wine tour of a tiny organic winery in Chianti and absolutely cherished it.

If time permits, we’d also recommend a stop at the lovely town of Badia a Passignano, a charming small town in the heart of Chianti.

Pro tip: If you’re acquiring Chianti Classico at home or elsewhere in Italy, confirm it says “Chianti Classico” (rather than just “Chianti”, which we learned can be made in other parts of Tuscany) and has an emblem of a rooster somewhere on the bottle, which is how you know it’s authentic.

Planning a Shorter Tuscany Road Trip Itinerary (3-5 Days)

If you have fewer than 7 days in Tuscany, our recommendation would be to focus your time on specific regions within Tuscany (see the geography overview above for how we’d break it up) rather than trying to see it all.

The initial thing to consider is whether you want Florence incorporated into your itinerary. You may have already visited it previously, or you may have more interest in the charming hilltop villages in the southern part of Tuscany.

If including Florence in your itinerary while also having constrained time, we’d recommend establishing yourself in Florence, and taking day trips to Siena, Lucca, or Chianti from there. In this scenario, we’d strongly advise against renting a vehicle!

We actually have a 3 day Florence itineraryfor you to basically copy, which includes a day excursion on the third day out into broader Tuscany.

If you have three days and Florence isn`t included, then we`d focus on one region (and we`d select either Siena or the Val d`Orcia).

If you have five days or so, focus on two regions – Siena and the Val d’Orcia.

You could organize your own itinerary based on your personal interests by utilizing the advice provided in the primary outline above!

5 Days in Tuscany: Siena and the Val d’Orcia

These two regions are quintessential Tuscany, at least in our view. Tuscany is famous for many aspects, but somewhere near the top of the list must be cypress trees and hilltop towns perched atop rolling hills as far as the eye can see.

That’s what you’ll find between Siena and the Val d’Orcia. If you only have five days, we’d split it between these two regions and completely avoid Florence and San Gimignano.

Here’s what that itinerary looks like: 

• Day 1: Drive to Siena
• Day 2: Siena + Monteriggioni
• Day 3: Val d’Orcia (Montalcino)
• Day 4: Val d’Orcia (Pienza & Montepulciano)
• Day 5: Val d’Orcia & Drive to Florence

3 Days in Tuscany: Siena & Around

Siena is a fantastic city, and like what was previously mentioned is likely the finest example of a charming hilly town within Tuscany. It’s a bigger city than the vast bulk of the additional smaller towns on this itinerary, and its beauty continues around each turn.

If you have three days in Tuscany, Siena makes for an excellent home base since it`s central to both San Gimignano and the Val d’Orcia, which renders a day trip more possible.

One idea for a shorter itinerary like this that is centered around Siena would be to take a day trip from Siena to reach either San Gimignano or the Val d`Orcia region.

The tradeoff of visiting one of those places means you have less time to explore Siena (you really only need about one and a half days, we think).

• Day 1: Arrive in Siena
• Day 2: Day Trip from Siena
• Day 3: Siena + Drive to Florence

In regards to the day trips, we`d strongly advise going with the company behind the walking tour we enjoyed in Siena. They offer a smaller group visit to the Val d’Orcia (Montepulciano and Pienza) and one heading west to San Gimignano and Volterra.

3 Days in Tuscany: The Val d’Orcia

As we have already covered multiple times, we love the Val d’Orcia.

The sole issue with the Val d’Orcia is that it is somewhat far from Florence, meaning you will spend a significant time in the vehicle between the two locations (roughly 90 minutes each way) for just a couple of days spent there.

However, we think exploring this region is worthwhile. This section of Tuscany is undoubtedly our preferred part.

Spending a relaxed couple of hours along the shores of Oak Creek.

• Day 2: Pienza & Montepulciano)
• Day 3: Morning Scenic Drive + Drive Back

---