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Writer's pictureAriela Bankier

Tuscany in 3 days: How To Plan the Perfect Three Day Itinerary in Tuscany


Planning the Perfect 3-Day Vacation in Tuscany: Top Tips from Someone Who Does This For a Living...


While I highly recommend spending at least 5-7 days in this breathtaking region to fully appreciate its beauty and offerings, I realize that not everyone can stay for that long. If you are in Tuscany for just a few days, know that it is absolutely possible to have an amazing experience even with just 3 days. But there are some things to keep in mind before you start planning.


So: what should you consider when crafting your itinerary? How can you maximize your time and ensure a memorable vacation within this limited timeframe? And what are the must-visit sites in Tuscany? Hopefully this post will provide you with valuable insights and guidance for your trip.


When planning your trip to Tuscany (or any destination, really), remember that the internet can be both your greatest ally and a potential source of trouble.

We all do research before our trips. And while I fully acknowledge the wealth of valuable information available online, I also recognize the unfortunate reality that some of it is misleading. From partial information and unreliable reviews to paid promotions and articles crafted by self-proclaimed experts recycling random snippets of data, it's easy to be misled.


Over the years I've encountered too many disappointed travelers who blindly trusted online recommendations or tips from Facebook groups, only to find that some restaurants and attractions gained popularity not for their quality, but due to effective digital marketing strategies. Take everything that you find online with a grain of salt, and, obviously, consider using an expert to craft your itinerary. Custom built itineraries are almost surpsingly well-priced, and offer excelelnt value for money.



The perfect 3-Day Itinerary in Tuscany is different for every person. It's really depends on your Personal taste. Begin by understanding what matters most to your group, and what isn't that important.

When my team and I create an itinerary for our clients, we begin by asking them to complete a detailed questionnaire. We do this because it's incredibly important to gain a clear understanding of each traveler's preferences and interests before we make any sort of suggestion for the itinerary itself. People are different, and have very different ideas regarding "the perefect Tuscan vacation". One shoe can never fit all :)

I enourage you to take a moment to reflect on what YOU truly love. What would your ideal vacation in Tuscany look like?


For instance, do you envision three days filled with breathtaking art, stunning architecture, and endless servings of hearty pasta paired with exquisite Chianti wine?

Or perhaps you’re a nature enthusiast who prefers hiking among the vines, sipping spritz cocktails on the beach, and sailing between the beautiful islands of Tuscany (yes, there are indeed several stunning islands to explore!).

Are you drawn to charming, ancient towns, the essence of Italian village life, and leisurely strolls?

Once you identify your primary interests and envision your ideal getaway, planning a solid itinerary becomes significantly easier. Of course, you may still want to include the “must-see” attractions in your schedule, but the overall experience will be better suited to you and your group, making it far more enjoyable.


If possible, go beyond the classic route. Many of the region's treasures hide off the beaten path...

Most websites/Facebook groups/blogs recommend sticking to the classic itinerary—Florence, Chianti, San Gimignano, Lucca, and Siena—during a three-day stay in Tuscany. This is understandable: each of these destinations is renowned for its beauty and charm. However, there is a lot to be said for exploring beyond the well-trodden path. There is an abundance of hidden gems waiting to be discovered, and adding just one unique experience to your itinerary can elevate a typical vacation into something truly unforgettable.


With these general tips in mind, let's move on to some specific examples.





3 Day Itinerary Tuscany: An Itinerary For Art Lovers

Florence, the capital of Tuscany, is renowned as one of the world's most beautiful cities. It's widely regarded as a true open-air museum, and an ideal destination for art enthusiasts. Here, you'll encounter breathtaking masterpieces created by legendary medieval and Renaissance artists, including Giotto, Masaccio, Michelangelo, and Leonardo da Vinci. The city is adorned with stunning churches featuring exquisite frescoes and is home to world-famous museums that draw millions of visitors each year. If art ignites your passion, allocate at least one full day to Florence, though two days would allow for a deeper exploration of this magnificent city.


Florence: the Must See Attractions

Key attractions include the Uffizi Gallery, which showcases remarkable works by Botticelli, Michelangelo, Leonardo da Vinci, Giotto, Caravaggio, and many others. Don't miss the Accademia Gallery, where Michelangelo's iconic statue, “The David,” resides. Additionally, visit the Santa Croce Church, known for its stunning frescoes and the tombs of notable figures such as Michelangelo and Galileo Galilei. Other highlights are the Bargello museum, the Santa Maria Novella church, the San Marco Monastery, and the magnificent Duomo of Santa Maria del Fiore, featuring Brunelleschi’s dome—an architectural marvel in its own right. To make the most of your experience, consider booking a small group or a private walking tour of the city center, or a guided visit to one of the city's best museums. Your visit will be richer and far more interesting with the expertise of a professional guide.


Siena: Definitely a Must See for Art Lovers

Siena may not be as renowned as Florence, but it is stunning, and definitely merits a visit. Even with only half a day to spare, you can explore the city's main attractions: the magnificent Duomo, one of Europe’s largest and most beautiful cathedrals; the iconic Piazza del Campo, where the famous Palio horse race occurs twice a year; and the historic Palazzo Pubblico, Siena's town hall. Take some time to wander through the ancient streets that have remained largely unchanged since the 14th century, and savor a delightful meal at one of the traditional Italian trattorie nestled among the red-brick alleys.

In the afternoon, venture out to the countryside for some wine tasting in the picturesque Chianti hills. If you need specific recommendations, or of you'd liek to join a wine tasting experience, simply email us at ariela@hamagaf.com


Pisa and Lucca: Beautiful Art and Architecture

Combining these two enchanting cities promises a perfect day for art enthusiasts. Pisa is renowned for its iconic Leaning Tower, alongside magnificent monuments like the stunning Duomo and the Baptistery. Lucca is a simply charming, and a joy to explore. Be sure to visit the Duomo of San Martino and the Church of San Michele, though for many, the best part about a visit to Lucca is the chance to wander through the vibrant streets and quaint piazzas.

You can rent a bike to ride along the impeccably preserved Renaissance ramparts, too, all while savoring the city’s lively food and wine scene. One of our favorite wine tasting experiences takes place in Lucca, and we warmly invite you to join us! Email us for details.

Pisa's Piazza dei Miracoli - the Duomo, the baptisterum, and the Leaning Tower

3-Day Itinerary in Tuscany for Travelers Who Enjoy Ancient Villages and Italian Cuisine

If you've already explored Florence, climbed the Tower of Pisa, toured Siena, and soaked in the charm of Lucca, it’s time to venture into the countryside and uncover some of Tuscany's enchanting ancient villages. Driving along the picturesque Tuscan roads, surrounded by rolling hills, vineyards, and farms, embodies the essence of a true Tuscan experience.

If you are based in Florence, you could focuse on some of the classic villages in the Chianti region, such as Greve in Chianti and Montefiorale, a hamlet that has remained unchanged for over a millennium. Castellina in Chianti and Gaiole in chianti are charming as well.

This is the perfect area to taste some excellent chianti wine, of course.


Alternatively, consider visiting Pienza and Montalcino in the enchanting Orcia Valley, in southern Tuscany. Few villages match the allure of these two popular destinations. Pienza boasts delightful alleyways, delectable cuisine, and stunning vistas, while Montalcino is renowned for one of Italy's most celebrated wines—the Brunello di Montalcino.


If you’re looking to recharge and unwind, consider adding a visit to the thermal baths in Rapolano Terme to your itinerary. A soak in the mineral-rich healing waters is the perfect way to soothe your body and soul after two intense days of sightseeing.

For more inspiration, especially if you're eager to explore off the beaten path, feel free to consult our travel guide Tuscany for the Shameless Hedonist, or reach out to us for a tailor-made itinerary.


If you'd like something different, why not visit Volterra and the Etruscan coast? Volterra is a small town renowned for its rich Etruscan heritage, which you can explore at the charming local Etruscan museum. The drive to Volterra is as breathtaking as the town itself, offering stunning views along the way! After visiting the museum, the Duomo, and the famous alabaster workshops, head south to the beautiful Etruscan coast and make a stop in Bolgheri.

Bolgheri is one of the most enchanting villages in Tuscany, a must-visit for any food and wine enthusiast. Some of best wine tours take place in this stunning region. Don’t forget to spend some time on the beach, savoring a spectacular Tuscan sunset while enjoying a refreshing cocktail in hand.


Tuscany is larger than you might expect. Contrary to the common assumption of many travelers, Tuscany boasts a significant size. When planning your vacation, aim to select destinations that are within a manageable driving distance from each other. Otherwise, you risk spending excessive time on the road and not enough enjoying the experiences that await you.

3 Day Tuscany Itinerary for Nature Lovers

If you have a passion for hiking, serene lakes, and hidden walking paths, know that Tuscany is also a true paradise for nature enthusiasts. There's an abundance to explore, from the northern mountains of the Garfagnana and Apuan Alps to the eastern forests near Arezzo, and down to the wild parks and stunning beaches of the Maremma in the south.

The Garfagnana boasts pristine hiking trails, ancient fortresses (be sure to look up Fortezza Verrucole), hidden lakes, and diverse wildlife.

In the Maremma, nature lovers can discover several attractions, such as the beautiful Parco della Maremma, renowned thermal springs (check out Terme di Saturnia), and some of Italy's finest beaches.

The Casentino Forest, located near Arezzo, is a wild expanse teeming with wildlife, enchanting waterfalls, and fantastic hiking opportunities.

What’s more, all three areas remain relatively undiscovered by mainstream tourism, making them a true gem for those seeking tranquility and natural beauty.


Tips for Visiting Tuscany: What is the Most Beautiful Part of Tuscany?

If you require assistance in navigating the abundance of online recommendations and creating the perfect itinerary tailored specifically for YOUR GROUP (not someone else’s), we’re here to help!

In addition to our custom built itineraries, we also offer food tours, wine tastings, winery visits, cooking classes, scenic hikes, and a diverse range of unique tours and activities. We'd love to help you discover the best of Tuscany, email us for a free quote: ariela@hamagaf.com


The rolling hills of the Val d'Orcia - Orcia Valley in Tuscany








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