With its iconic cities, beautiful hilltop towns, world-famous wineries, and glistening, golden light, it’s no surprise that spending a few days in Tuscany is one of the most popular additions to first-timers’ Italy itineraries!
If you’re planning your first trip to the region and are curious about how to make the most of a short but sweet 3 days in Tuscany, this guide is for you (and if you happen to have more time in the region, here’s our recommended Tuscany road trip itinerary).
We’ve spent months traveling Tuscany in-depth over the years, and have experienced the region in just about every way possible: on a budget, on a splurge, with a car, via train, as a couple, with extended family… and no matter which style of trip we take, we always walk away enchanted by the region’s food, beauty, wine, and warm people.
When it comes to the logistics of planning a trip to Tuscany, though, we know that it can be tough to narrow down exactly how to structure your trip–especially when many of the best places to visit in Tuscany are small towns that can be a bit harder to access than major cities are.
While you can’t see more than a small sample of Tuscany in 3 days, you can absolutely see enough to make your trip incredibly memorable.
Here’s everything you need to know about planning a 3 day trip to Tuscany!
Where Exactly is Tuscany, Italy?
At the very beginning of your planning journey and curious about what exactly Tuscany is–beyond being a collection of idyllic photos of hilltop towns and rolling hills?
Tuscany is one of Italy’s 20 administrative regions and a fairly large one at that!
Located on the western coast of the country (yes, Tuscany has beaches and even islands!), Tuscany is considered part of Central Italy.
It’s bordered primarily by the regions of Emilia-Romagna (home of Bologna) to the northeast and Umbria to the southeast, though it also touches Lazio (home of Rome) to the south, Marche to the east, and Liguria (home of Cinque Terre) to the northwest.
Florence is the capital city of the region of Tuscany.
How We Structured These Ideas for 3 Days in Tuscany
In a region as big as Tuscany, designing the perfect itinerary for your visit is less about seeing it all than about prioritizing what you want to see.
For one example, to drive from Florence to Saturnia (Tuscany’s most iconic hot spring) takes more than 3 hours each way–and with hundreds of places worth visiting in Tuscany, you’ll likely find the drive isn’t worth it if you only have a few days to spare.
To help you narrow it down, we’ve outlined a handful of short Tuscany itineraries in this blog post, each filled with places that we adore that are also popular with first-time visitors.
We’ve intentionally kept this guide to spending a few days in Tuscany fairly high-level, and avoid getting bogged down into too many details about how to spend time in a particular destination.
Where possible, we’ve linked to the relevant blog posts that we’ve published about each place–but with 100+ blog posts about Italy on Our Escape Clause, it’s safe to say we haven’t been able to link to them all!
If you’re curious about our coverage of a certain destination, you can also use the search bar in the top right-hand corner of the screen (or on the pop-out menu, on mobile) to see what blog posts we have about a given city or town.
Should you rent a car for 3 days in Tuscany?
When planning a trip to Tuscany, the first question you need to ask yourself when choosing an itinerary is whether or not you want to drive.
Do you need to rent a car in Tuscany?
No, ultimately it’s not necessary: between trains, buses, and organized day trips, you can enjoy a wonderful and fulfilling trip without getting behind the wheel, especially when you’ll only be in Tuscany for 3 days!
However, if you’re a confident driver who hopes to easily and independently access smaller villages without train stations (or with train stations that are a few kilometers away from town–a common issue with hilltop towns), get off the beaten path, or stay in the countryside (including renting a villa, for example), then you’ll need a car for visiting Tuscany.
We’ve enjoyed Tuscany both with and without a car over the years and while there’s no right or wrong answer to this question, there may be a clear right answer for you!
The 3 day Tuscany itineraries we’ve outlined below feature options both with and without a car, so see what style of trip appeals to you!
If you’re on the fence about whether driving in Tuscany for a few days sounds idyllic or stressful, check out our driving tips in our Tuscany road trip guide–they’ll give you a good idea of what to expect.
If you do decide to rent a car in Tuscany, we recommend searching through Discover Cars, which will allow you to compare prices and inclusions of multiple companies at the same time and choose the best car for you from there.
Exciting 3 Day Tuscan Itinerary Ideas (Perfect for First-Timers)
With hundreds of places to visit and experiences to enjoy (like a cooking class, for example!), there is a near-infinite number of ways to structure a 3 day Tuscany itinerary.
To help you narrow it down and get a feel for what you can accomplish with a few days in Tuscany, we’ve designed each of these sample itineraries to focus on some of the most popular places in Tuscany for first-time visitors.
One of these options is designed to visit with a car and two are organized around visiting Tuscany without a car, but you can easily mix and match depending on your wish list and travel style!
Classic Introduction to Tuscany Without a Car: Florence, Hill Towns, and Wineries
For the most classic 3 day introduction to Tuscany (no car needed), this Florence-focused itinerary is a great option.
It’s also the one we recommend in our suggested 2 week Italy itinerary!
Day 1 and 2: Florence
Start your first couple of days in Tuscany by diving deep into the region’s beloved capital city!
Our recommended 2 day Florence itinerary covers how to make the most of your time here in more detail, but a few things to look forward to include visiting Florence’s iconic Duomo, strolling across the Ponte Vecchio, enjoying lots of Tuscan food, and browsing markets for cheese, leather, and more.
Of course, the famous Uffizi Gallery (we loved this tour) and Galleria dell’Accademia (home of Michelangelo’s David) are must-visits as well!
And, no visit to Florence is complete without seeking out some of the best views of the city, whether that’s from the top of the Duomo, Piazzale Michelangelo, Palazzo Vecchio (one of our favorites), or beyond.
Day 3: Organized Day Trip to Hill Towns and Wineries
After exploring the best of Florence for a couple of days, it’s time to take to the hills!
Organized day trips to the Tuscan countryside, like this wildly popular one, can be an incredible value if your goal is to sample a variety of what makes this part of the world so special, without worrying about transportation (including a designated driver!), parking, or time.
This excellent day trip includes visits to the beautiful city of Siena and the classic hilltop town of San Gimignano, plus lunch at a family-operated vineyard in the Chianti wine region.
While fast-paced, the itinerary is very doable with a small group run by a knowledgeable guide–but it would be logistically difficult to visit all of those places in one day alone, and without a car, almost impossible.
Classic Introduction to Tuscany With a Car: Siena, Montepulciano, the Val d’Orcia
Looking to plan a quick 3 day road trip through Tuscany?
If so, this itinerary through some of Tuscany’s most beautiful towns, villages, and rolling hills is for you!
Day 1: Siena
The medieval military rival of Florence, the beautiful city of Siena is a (slightly) less crowded and smaller option for basing yourself during 3 days in Tuscany–and as a bonus, it’s much closer to the famed Val d’Orcia than Florence is!
While in Siena, don’t miss the striking, oval-shaped Piazza del Campo (home to the famous, bi-annual Palio di Siena horse race), the mesmerizing Siena Cathedral, or the view from the Torre de Mangia.
To see the best of the Duomo di Siena, we loved taking the Gate of Heaven tour to access the building’s rooftops and terraces–it’s one of our favorite things to do in Siena!
Don’t miss the view from the Panorama by the Unfinished Facade when exploring the cathedral complex, either. That’s where we snapped this photo of what is arguably Siena’s most famous view:
Day 2: Montepulciano + Wine Tasting
On the second day of your mini 3 day Tuscan road trip, head directly to Montepulciano!
This hilltop town is a favorite among visitors to Tuscany, ourselves included, and is famous for its wine, views, and beautiful town center.
Start your morning in the historic center of Montepulciano (like virtually all Tuscan hilltop towns, you’ll need to park outside the center and climb a bit to the top–but it’s worth it!).
Be sure to see the beautiful Piazza Grande, step inside one of Montepulciano’s famous wine cellars, admire the views from the Medici Fortress, and browse the shops and cafes (we love Caffe Poliziano and stop by every time we visit Montepulciano–don’t miss the views from the terrace out back!).
After enjoying Montepulciano itself–and possibly stopping outside the center to enjoy the Church of San Biagio–wine lovers can head to a nearby vineyard for a wine tasting.
Don’t want to drive any further?
Don’t worry–Montepulciano’s wine cellars located right in town have you covered (we loved Cantina de Ricci, and this organized visit is also a great way to explore).
Day 3: The Val d’Orcia
Located about an hour south of Siena by car, the legendary Val d’Orcia is home to some of Tuscany’s most cherished and iconic landscapes–and the landscape itself is even recognized as a UNESCO World Heritage Site!
Rolling hills framed by tall cypress trees, golden light, picturesque towns, and some of Tuscany’s most iconic photo spots (like the Chapel of Madonna di Vitaleta, for example) can all be found here.
Towns like Pienza, Montalcino, and Monticchiello make excellent destinations when exploring the Val d’Orcia, and we recommend visiting at least two of them during your final day in Tuscany, but simply driving through the landscape and appreciating the views is also a good portion of the fun!
If you have your heart set on visiting any of the most famous photography spots in and around the Val d’Orcia, be prepared for crowds–especially if you’re visiting in the high season and/or around sunset.
There’s no doubt that the views in this ethereal valley are truly something special, though: there’s a reason that the Val d’Orcia is so enduringly popular with photographers, painters, and travelers alike.
Independent Tuscany Itinerary Without a Car: Florence, Lucca, Pisa, and Siena
Want to avoid both driving in Tuscany and taking any kind of organized tour?
If so, this easy 3 day Tuscany itinerary–which can be completed entirely by train–is for you!
This itinerary is simplest to accomplish by train when based in Florence, but if you plan carefully and don’t mind a couple of longer train rides with transfers (travel between Siena and Lucca isn’t direct, but doable), you can technically stay in any of the highlighted cities on this route.
I will add a twist, though: if you’d like to rent a car for just one day, you could also take the third day of this itinerary to visit a couple of smaller villages–perhaps San Gimignano and Volterra–on a mini road trip, combining the best of both worlds for your Tuscan getaway!
Day 1: Florence
With only one day in Florence, you won’t be able to cover as much as in our first Tuscan itinerary suggestion above–but despite its world-class art and fame, Florence is a fairly small city!
Over a single (well-planned) day, you can easily pay a visit to the Duomo, seek out a viewpoint or two, visit David in the Galleria dell’Accademia or the Uffizi (or if you’re a true Renaissance art-lover, both), wander across the Ponte Vecchio, and go piazza-hopping through the historic center.
If you close out your day by admiring the view from Piazzale Michelangelo at sunset followed one last gelato while people-watching in a piazza (we’re partial to Piazza Signoria for this), you’re bound to walk away feeling like you’ve enjoyed a beautiful introduction to Florence.
For more detail, here’s our recommended one day Florence itinerary!
Day 2: Siena
From one stunning Tuscan city to the next: on the second day of your Tuscany vacation, hop a train south to Siena!
Once you arrive and make your way up to the historic center, you’ll want to follow the same outline as suggested in the second itinerary recommendation above: Piazza del Campo, Siena’s beautiful Duomo, and the view from the Panorama should all be on your priority list.
If you do thorough justice to the Duomo Complex (as you should!), enjoy a leisurely lunch, and perhaps stop by the fresco-covered Santa Maria Della Scala Hospital, you’ll find that you can easily fill a day trip to Siena from Florence!
Day 3: Lucca + Pisa
When planning a 3 day trip to Tuscany without a car or the desire to book an organized day trip, by far the simplest destinations to round out visits to Florence and Siena with are Lucca and Pisa (where you can, of course, climb the iconic leaning tower).
Lucca in particular is one of our favorite cities in Tuscany, and is famous for its intact town walls, for being the “City of 100 Churches” (more than one complete with a mummy!), its oval-shaped Piazza dell’Anfiteatro, and its unique Torre Guinigi, where you can enjoy a garden in the sky while admiring views of Tuscany.
Relaxed, easy to wander through, and absolutely beautiful, it’s an amazing place to visit in Tuscany!
Pisa, while not generally quite as well-loved as Lucca among repeat Tuscany visitors (ourselves included), is of course home to a very famous tower… that’s even more beautiful in person than it is in photos.
While we wouldn’t recommend spending a full third of your trip to Tuscany in Pisa, and you’ll definitely want to book your tower climb in advance, if you’ve long dreamed of seeing the Leaning Tower of Pisa, combining a stop there with a visit to Lucca is a great way to round out 3 days in Tuscany.
If you time the trains right, Lucca and Pisa are only about 30 minutes apart and are therefore easy to combine into one excellent day trip from Florence.
Tips for Spending a Few Days in Tuscany
Narrow down which part of Tuscany you hope to visit.
Tuscany is a surprisingly big region, as well as a (perhaps not so surprisingly) rural one, especially once you step off the beaten path!
After enough trips to Tuscany that we’ve lost track of how many times we’ve visited, we still haven’t seen everything we hope to–and part of the reason for that is that the distances involved are really too far to be able to day trip to every point in Tuscany from another.
With only a few days to enjoy the region, we recommend concentrating your itinerary geographically, if possible.
Florence, in north central Tuscany, can easily be combined with places like Lucca and Pisa to the west, as well as the Chianti wine region to the east, and San Gimignano to the southwest.
The area surrounding Siena is perfect for accessing places like Volterra, Monteriggioni, the Val d’Orcia, and Montepulciano (via a day trip).
Montepulciano itself makes a wonderful base for exploring the famous Val d’Orcia to the west (including towns like Pienza and Montalcino), as well as Cortona (the town from Under the Tuscan Sun).
Some famous places, like Saturnia, are surprisingly far away to access on a first-time Tuscany itinerary, though certainly doable if it’s a priority for you!
Don’t rule out guided day trips–especially to wineries!
If your goal is to see a wide variety of the Tuscan countryside in one day, enjoy a wine tasting without worrying about anyone in your party being safe to drive afterward (and given the generous pours at Tuscan wine tastings, odds are that no one drinking will be!), or some combination of both, absolutely do not rule out signing up for an organized day trip in Tuscany!
While not all day tours around the world offer good value for money, in Tuscany they are generally a very good value (as long as they fit into your budget, of course).
Generally, with a tour, a first-time visitor will be able to see more with less time and access memorable experiences like farmhouse lunches with perfect views that–while certainly not impossible to source independently–require far more work to access alone than simply signing up for a day trip.
Some of our most memorable moments of travel in Tuscany have taken place as part of guided experiences!
With 3 days in Tuscany, this popular day trip (offered by one of our favorite tour companies in Italy) is a particularly good option for several itineraries.
Renting a car for part of your trip is often an excellent compromise.
While we’ve outlined the possible 3 day Tuscany itineraries included here to be all-or-nothing when it comes to renting a car, you absolutely don’t have to plan your trip that way!
If you’d like the best of both worlds, you can base yourself in a city like Florence, Siena, or Lucca, and then rent a car for just one day to explore the countryside independently.
Not only does this option cut down on the costs of renting a car, but it’s also immensely less stressful than being responsible for a rental car overnight when staying in a city, where navigation and parking are significant challenges.
If you’re visiting Tuscany with a car, decide where to park before you leave.
This is one of our favorite tricks to keeping stress levels down when driving into a new town in Tuscany: know where the public parking lots are and, when heading out for the day, put your directions on for that particular spot rather than just the town.
This dramatically cuts down on the risk of accidentally driving into a ZTL zone/limited traffic zone (and therefore getting a ticket) and also makes the trip into town far less stressful.
Now, in the interest of full disclosure, this doesn’t always work–occasionally the parking lot you have picked out will be full, or you’ll luck out and find street parking along the way–but in general, it will definitely make your few days in Tuscany much easier.
Be prepared for steep climbs when spending a few days in Tuscany.
Tuscany is known for its delightful hilltop towns, full of winding, narrow streets and plenty of foot traffic.
Combine the above description of Tuscany that we all know and love with the very concept of a Tuscany road trip, and an obvious question emerges: where are the cars?
Usually, they’re in parking garages built literally under the hilltop towns or on the outskirts of historical centers… which means you often have to walk up steep hills to reach the center.
Some cities, like Siena, have escalators installed to help alleviate this problem–but in general, be prepared for a little bit of a leg workout when visiting small towns in Tuscany!
FAQ For Spending 3 Days in Tuscany
Is 3 days enough for Tuscany?
While a lifetime probably isn’t long enough to uncover all of Tuscany’s secrets and hidden gems (we’ll try our best!), if your goal is to balance an introduction to Tuscany with a chance to see other parts of Italy as well, a few days in Tuscany is definitely enough to enjoy your first trip.
With a full 3 days in Tuscany, you’ll have a chance to see a Tuscan city or two, sample the countryside, learn about the iconic cuisine, sip local wine, and admire views from hilltop towns.
While there’s a good chance you’ll say goodbye after a few days in Tuscany already ready to plan your next trip back, you’ll also have enough time to enjoy a nice variety of what makes the region so special.
What are the best places to visit during your first trip to Tuscany?
Some of the most popular places to visit in Tuscany include Florence (the capital city of the region), Siena, Montepulciano, Pisa, Lucca, the Chianti wine region, San Gimignano, and the Val d’Orcia.
However, anywhere that tickles your fancy is well worth visiting!
Some of the other incredible places to visit in Tuscany include Saturnia (as well as many lesser-known hot springs like Bagno Vignoni), Arezzo, Cortona, the island of Elba, and the beach town of Forte dei Marmi.
In addition to specific towns and cities, unique experiences, like this Tuscan cooking class we loved, horseback riding in the countryside, and Vespa tours (we adored this one) also top many Tuscany bucket lists!
Is Tuscany or Florence better to visit?
This is a common point of confusion with first-time visitors, but Florence is in Tuscany–in fact, Florence is the capital city of the region!
For that reason, Florence is one of the easiest bases to use in order to take day trips to Tuscan hill towns and wineries in the countryside, which is often what people are referring to when they talk about visiting Tuscany for the first time.
Do you need a car in Tuscany?
You can easily make an argument for or against renting a car in Tuscany, but here’s the shortest answer: while you do not need a car to enjoy a trip to Tuscany, there’s a good chance you will want one in order to pull off your dream trip!
However, while driving in Tuscany is easier than in some places in Italy, it’s best suited for confident drivers who drive regularly as part of their daily lives.
What is the best month to visit Tuscany?
While we would never turn down a trip to Tuscany in any month of the year, our personal favorite months to visit Tuscany are September and October, for crisp fall weather, slowly diminishing crowds (though the crowds seem to stick around longer every year), and the wine harvest.
November, when the olive harvest happens and fresh olive oil hits the shelves (it’s never tastier than the moment it’s pressed!) is also a favorite.
April and May are also very popular, in order to enjoy all the best of spring in Tuscany, including bustling markets and blooming flowers, and also have a chance to visit Tuscany before schools let out and crowds pick up for the summer.
Winter is very quiet in Tuscany, especially in small towns, but is also the least expensive time to visit.
Read More About Visiting Tuscany
Ready to keep planning your upcoming 3 days in Tuscany?
We’d love to help!
You can browse our 100+ Italy blog posts here, or check out these guides:
- Secret Florence: Off the Beaten Path Spots + Traveling Slowly in Tuscany
- The Outsized Charm of Tiny Montefioralle, Italy
- How to Take the Perfect Day Trip to Florence from Rome
- 25 Best Movies Set in Italy (By Genre!)
- How to Plan the Perfect Honeymoon in Tuscany
Hi Kate: My husband and I are coming to this beautiful reagion in October and would love to have you guide us around. Please let me know what we should do at this point. We have been to florence and have seen all the tourist attrations. We want to visit the wine country of tuscany and the villages. We only have 3 days. October 1-4. If you can be our guide we will not rent a car. We are not sure where to make our base. Please let me know your thoughts and if you are interested in being a part of this adventure. we are a bit older, 70 and 66. Thanks for talking with us.
Hi guys,
Thank you so much for thinking of us! However, we’re not travel agents or tour guides (and in fact, being an official tour guide in Italy is quite an involved process that involves years of study and requires a license).
Our travel guides are meant to help independent travelers plan their trips, and if you decide to go that direction, we’re always happy to answer a few questions!
Hope you guys have a fantastic time in Tuscany. 🙂
Hi Kate, do you have any lodging recommendations in Florence? Planning to spend 2 nights and 3 days in Florence on our 10 days in Italy. Thanks!!
Hi Rachel,
Yes, absolutely! This is the guide I’ve updated most recently with Florence hotels: https://www.ourescapeclause.com/2-weeks-in-italy-itinerary
Hope you guys have a fantastic trip!
Hi there, I am going in Tuscany this coming March 2025, arriving March 12, going to Florence on March 15. We are getting our rental car from Florence main train station. My question is can you advise me where to base in that short period of time? Our main goal is to visit Siena, leaning tower of Pisa, San G and second is to visit wineries for wine tasting. Are those number of days doable to do all of this? Or we have to add one more day. I am just worried that it might be too quiet in Tuscan region during those dates. Pls advise! Thank you!
Hi Marie!
First things first: it definitely won’t be too quiet in Tuscany in March! Relish what quiet you find, as it’s increasingly hard to find any time of year in the most popular places in the region. 🙂
If I’m understanding right, you’re saying that you have part of the 12th (the day you arrive), the 13th, and the 14th explore Tuscany outside of Florence, and then on the 15th you head to Florence and will visit the city.
So, if I have it right, yes, you can visit all four of the places you mentioned (Siena, Leaning Tower, San Gimignano, wineries) briefly in that amount of time!
Personally, I wouldn’t allot too much time to Pisa and the Leaning Tower–a half day max should do it. If you just want to see the tower, you could even stop by on your way back to Florence on the 15th. We have a couple of posts about Pisa, this one covers my thoughts on climbing the tower specifically: https://www.ourescapeclause.com/climbing-the-leaning-tower-of-pisa/
There are some beautiful wineries outside of San Gimignano, Tenuta Torciano is a fairly famous one that we loved. If you want to do several wine tastings, you might consider signing up for an organized day trip from either Florence or Siena rather than driving yourselves, as you’ll need a designated driver with the way Tuscan wineries pour! If someone in your group is willing to drive, though, you can easily combine a stop at a winery with visiting San Gimignano, which is fairly small.
Siena can easily eat up a full day or more, it’s the largest and most time consuming place on your list. You can get a decent snapshot of it in a day, though! Here’s our post about it: https://www.ourescapeclause.com/siena-day-trip/
If you want to stay in town somewhere, I’d opt to base yourself in Siena or San Gimignano for ease, since you already want to see them both. If you’d rather stay in an agriturismo, though, one near-ish San Gimignano would make sense geographically.
Depending on how fast you sightsee, you might also look into visiting Monteriggioni, which is small, beautiful, and right between Siena and San Gimignano.
Hope you have a wonderful trip!