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3 Days In Tuscany- 5 Different Creative Ways To Plan Your Trip

Even if you have only 3 days in Tuscany, you’ll be able to feel that there’s a certain magic to this region that can’t be found anywhere else in the world. With its rolling hills and cypress trees, charming medieval towns, and vineyards, this is a place where beauty seems to be everywhere you look. The sun-drenched landscape is like a painting that changes with the seasons, from the vibrant greens of spring to the golden hues of autumn.

Here, time seems to slow down, and you’re reminded to savor each moment. Whether you’re exploring the narrow streets of Florence, sipping wine in the countryside, or simply taking in the breathtaking views, Tuscany is a place that will leave you feeling enchanted and inspired. If you’re planning to visit the beautiful region of Tuscany anytime soon, keep reading, this Tuscany in 3 days itinerary planner will surely help you make your trip even more amazing.

Let’s start from the beginning…

Getting Around Tuscany

tuscany for first timers

Exploring the region’s picturesque countryside and charming towns is an incredible experience, and with just 3 days in Tuscany, you’ll want to make the most of your time. Fortunately, there are many ways to get around Tuscany to see all the highlights. Renting a car gives you the most flexibility, allowing you to venture off the beaten path and discover some of the region’s finest hidden gems. You can use this link to compare the deals from all car rental companies in the area and get up to 30% off. 

If you prefer public transportation, taking the train is a great option for exploring Tuscany’s major cities such as Florence and Siena. Buses are also available to visit smaller towns and villages while renting a scooter or bike offers a unique and adventurous way to explore the region. Whichever way you choose, getting around Tuscany is easy and provides a great opportunity to experience the region’s rich culture, stunning landscapes, and delicious cuisine.

Best Time To Visit Tuscany

visit Tuscany for the first time

The best time to visit Tuscany depends on your preferences and what you want to experience. Spring and fall offer mild temperatures and fewer crowds, making it a great time to explore Tuscany’s picturesque towns and countryside. The blooming flowers and lush greenery of spring provide a beautiful backdrop for scenic drives and bike rides, while fall offers the opportunity to experience the region’s wine harvest and festivals. 

Summer is the peak tourist season, with warmer temperatures and longer days ideal for outdoor activities and sun-soaked adventures. However, expect crowds and higher prices during this time. Winter is the off-season, with cooler temperatures and shorter days, but it’s an excellent time to experience Tuscany’s Christmas markets and cozy indoor activities. 

Helpful Resources For Visiting Tuscany

If you’re looking for a cheap flight to Florence, this Qatar Airways link will get you up to 15% off (I use it too for most of my bookings).

Travel insurance is an essential requirement for traveling to Italy, and if you don’t already have one, SafetyWing offers affordable plans that cover medical expenses, as well as other miscellaneous travel expenses like delayed flights and lost baggage.

Auto Europe is providing a special discount on car rentals in Florence, which can offer up to 25% off (for more info on their services check out our Auto Europe review).

If you’re looking for train and bus rides in Italy, you can use Busbud to book transportation to and from Florence and get up to a 10% off when using my link.

You can save up to 15% on all properties in town by using our special offer through Booking. If you’re looking for a hotel in Florence, you may also like our Hotel Lungarno review.

It’s important to obtain a visa if required, and you can check if you need a visa and apply through iVisa. They take care of all necessary arrangements for you, making the process much easier and personally, I use their services all the time.

We also have a guide to hidden gems in Italy and a list of things you can find only in Italy to help you discover more about the country.

Finally, to help you plan your trip to Italy, we have prepared a guide to visiting Italy on a budget and a guide to planning a 10-day Italy itinerary.

Best Tours To Take In Tuscany

Tuscany offers a plethora of tour options that cater to all types of travelers. From food and wine tours that showcase the region’s culinary excellence to historic tours that transport visitors back in time to the Renaissance era, and nature tours that allow for an immersive exploration of Tuscany’s breathtaking landscape, there is something for everyone. With expert local guides who are passionate about the area, visitors can delve deeper into the rich culture and history of Tuscany. Here are some of our favorite tours that will hopefully help you make the most out of your trip to Tuscany.

This Florence walking tour is a great way to get introduced to the main highlights of Tuscany’s capital.

If you’re into cooking tours, you’ll love this pizza and gelato preparation class in Florence.

If you’re in Siena and don’t have a lot of time to spend this guided walking tour with skip-the-line tickets is a great choice.

For one of the best culinary experiences in the region, check out this Montalcino food tour (with wine tasting).

How To Spend 3 Days In Tuscany?

Arcetri Astrophysical Observatory

Tuscany is an exciting region and as soon as you arrive, you’ll notice why it’s one of the most visited regions of Italy. Tuscany was the birthplace of Renaissance (meaning you’ll find a lot of historical sites, museums, and galleries), it’s one of the best culinary destinations in Italy, and it has charming rolling countryside, and even a few beautiful beaches. That’s why we have prepared a few different creative itineraries for different kinds of travelers, so whether you’re into history, food, wine, or nature, or are looking to explore with your loved one/family, we have you covered.

3 Days In Tuscany- Itinerary For Wine Lovers

Tuscany is a famous wine region in Italy, known for producing some of the world’s finest wines. With its beautiful countryside, rolling hills, and vineyards, Tuscany offers an ideal setting for wine enthusiasts to indulge in their passion. This itinerary allows you to explore the wine cellars, learn about the winemaking process, and taste some of the best wines that Tuscany has to offer. 

Day 1- Chianti 

chianti 3 days in tuscany

Begin your wine adventure with a visit to the Chianti region, famous for its world-renowned wine production. Start your tour at the Castello di Brolio, a medieval castle that offers a stunning view of the surrounding vineyards. Afterward, visit the nearby Ricasoli Winery, the oldest winery in Italy, and enjoy a wine-tasting experience paired with local cheeses and cured meats.

Day 2 – Montepulciano


Head south to the Montepulciano region, known for its Vino Nobile di Montepulciano (famous wine variety). Visit the Poliziano Winery and take a tour of their underground cellars, followed by a tasting of their award-winning wines. After lunch, head to the Avignonesi Winery to learn about biodynamic winemaking methods and enjoy their organic wines.

Day 3- Montalcino

montalcino 3 days in tuscany

End your trip with a visit to the charming town of Montalcino, famous for its Brunello di Montalcino wine. Start your day with a visit to the Castello Banfi Winery, where you can take a tour of their vineyards and cellars and indulge in a tasting of their Brunello di Montalcino wine. Afterward, visit the Il Paradiso di Frassina Winery, known for its unique approach to winemaking by playing classical music to its vines.

Finally, explore the town of Montalcino and enjoy a traditional Tuscan lunch at one of the local restaurants. Our two favorite recommendations are Moro, famous for its traditional Tuscan cuisine, particularly its handmade pasta, fresh seafood, and grilled meat, all prepared with locally sourced ingredients, and Locanda Demetra, famous for its homemade pasta and special sauce and the beautiful views of the surrounding countryside.

Enjoying this post? Then you may also like our list of hidden gems in Venice or our guide to Venice in one day.

3 Days In Tuscany– Itinerary For History Buffs

Tuscany is a region steeped in history, with numerous ancient towns and landmarks. Florence, the region’s capital, is a treasure trove of Renaissance art and architecture, home to world-famous museums and landmarks but the region is also home to plenty of other noteworthy attractions, including the famous Siena Cathedral, the Etruscan tombs of Volterra and the hilltop fortress of Monteriggioni, etc. This itinerary will help you cover most of the region’s most popular historical sites.

Day 1- Florence

Palazzo Vecchio

Begin your trip to Florence, the birthplace of the Renaissance. Start your tour at the iconic Duomo, a stunning cathedral with a colorful marble facade and a breathtaking dome designed by Brunelleschi. From there, head to the Uffizi Gallery (get a cheap skip-the-line ticket), one of the most important art museums in the world, housing masterpieces by Botticelli, Michelangelo, and da Vinci. Continue by taking a walking tour and cover some of the city’s main highlights like the Ponte Vecchio, Il Duomo, and Piazzale Michelangelo). Finally, visit the Palazzo Vecchio, a medieval fortress turned town hall that showcases a fascinating blend of Gothic and Renaissance architecture.

If you’re looking for some more suggestions, check out our list of unusual things to do in Florence.

Day 2- Siena


Explore the medieval town of Siena, known for its narrow streets, beautiful piazzas, and rich history. Start your tour at the Piazza del Campo, the heart of the city and the site of the famous Palio horse race. From there, visit the Siena Cathedral, a Gothic masterpiece with stunning frescoes and a unique black-and-white striped facade. Finally, explore the Palazzo Pubblico, the town hall that houses the famous fresco series “The Allegory of Good and Bad Government” by Ambrogio Lorenzetti.

Day 3- San Gimignano

san gimignano

End your trip in the beautiful medieval town of San Gimignano, known for its majestic towers and breathtaking views. Start your tour at the Collegiate Church of San Gimignano, a Romanesque church with stunning frescoes and a beautiful marble facade. From there, explore the town’s famous towers, including the Torre Grossa, the tallest tower in San Gimignano that offers panoramic views of the surrounding countryside. Finally, visit the Museum of Sacred Art, which houses a stunning collection of religious art and artifacts from the region’s rich history.

3 Days In Tuscany– Itinerary For Foodies

Tuscany is a foodie paradise, offering some of the best culinary experiences in Italy. From hearty pasta dishes like Pappardelle alla lepre to the famous Chianina beef, and delicate desserts like Cantucci and Vin Santo, every meal is a treat for your taste buds. But it’s not just about the food – it’s the whole experience that makes Tuscany special. Imagine sitting at an outdoor cafe, surrounded by the stunning Tuscan countryside, savoring a delicious plate of fresh pasta and sipping a glass of local wine. Tuscany truly is a culinary dream come true and our itinerary will help you make the most out of it.

Day 1- Florence

florence food

Begin your trip in Florence, a city known for its hearty, rustic dishes that shaped Tuscan cuisine throughout the years. Start your tour at the Mercato Centrale, a bustling indoor market with vendors selling fresh produce, meat, cheese, and more. From there, head to the nearby Trattoria da Mario for a classic Tuscan lunch of pasta al ragù, grilled meat, and red wine.

Next, visit the Officina del Gelato for a sweet treat of artisanal gelato made with local ingredients. Lastly, take a walking tour and explore some of the city’s iconic sights before ending this delicious day with the traditional aperitivo in one of the local wine bars.

Day 2- Montepulciano

Montepulciano 3 days in italy

Explore the charming town of Montepulciano, known for its delicious wine and traditional cuisine. Start your tour at the Piazza Grande, the town’s central square, and visit the Palazzo Comunale, a beautiful medieval town hall that houses a collection of art and artifacts. From there, head to the nearby Osteria Acquacheta for a lunch of hearty meat dishes and local wines. Finally, visit the Cantina Contucci, a historic winery that offers wine tastings and tours.

Day 3- Greve 

greve 3 days in tuscany

End your trip in the picturesque town of Greve in Chianti, known for its beautiful countryside and world-famous wine. Start your tour at the Mercato delle Cose Buone, a weekly market that showcases the region’s best food and drink. From there, head to the nearby La Cantina del Gallo Nero for a lunch of delicious pasta dishes and Chianti Classico wines. Finally, visit the Castello di Verrazzano, a stunning Renaissance castle that offers wine tastings and tours of its vineyards and cellars.

3 Days In Tuscany– Itinerary For Nature Lovers

Tuscany’s nature and countryside offer stunning landscapes of rolling hills, lush vineyards, and olive groves. The region is home to several natural parks, such as the Maremma Natural Park and the Apuan Alps, where you can hike, bike, or horseback ride while enjoying the breathtaking views. The countryside also provides opportunities to explore charming medieval towns, such as San Gimignano and Volterra, where you can experience the slow-paced lifestyle and traditional Tuscan cuisine. Don’t miss the chance to immerse yourself in the beauty and serenity of the region’s natural wonders even if you have only 3 days in Tuscany.

Day 1- Montalcino

Montalcino view

Start your trip in the beautiful town of Montalcino, known for its stunning countryside and world-famous wine. Begin your tour at the Fortezza di Montalcino, a beautiful fortress that offers panoramic views of the surrounding hills. From there, head to the nearby La Crocina di Montalcino for a lunch of traditional Tuscan dishes and local wines. Finally, visit the Fattoria dei Barbi, a historic winery that offers wine tastings and tours of its vineyards.

Day 2 – Val D’Orcia

val d orcia

Explore the breathtaking Val d’Orcia, a UNESCO World Heritage Site known for its rolling hills, charming villages, and beautiful landscapes. Start your tour at the Abbey of Sant’Antimo: A beautiful Romanesque abbey located in a peaceful valley. Attend a Gregorian chant performed by the monks and take in the serene atmosphere. You can also take a hike in the Crete Senesi, a region famous for its scenic rolling hills and clay formations or enjoy a picnic in the nature.

In the afternoon, you can visit the town of Pienza, a Renaissance gem that offers stunning views of the surrounding countryside. From there, head to the nearby Agriturismo Il Rigo for a lunch of farm-to-table cuisine made with local ingredients. Finally, visit the nearby Bagno Vignoni, a picturesque village with a beautiful thermal bath that offers stunning views of the surrounding hills.

Day 3- Maremma

Maremma 3 days in italy

End your trip in the beautiful Maremma region, known for its stunning coastline and pristine nature reserves. Start your tour at the Parco della Maremma, vast protected area covers over 10,000 hectares of forest, hills, and coastline, offering a diverse range of ecosystems and wildlife. Maremma is also home to many rare and endangered bird species, making it a prime destination for birdwatching. Head to the Orbetello Lagoon or the Nature Reserve of Diaccia Botrona for the best birdwatching opportunities.

From there, head to the nearby Osteria Etrusca for a lunch of fresh seafood and local wines. After lunch, you can relax on the beach or take a swim in the crystal-clear waters of the Tyrrhenian Sea or explore the ancient ruins of Roselle or the Necropolis of Sovana to learn about the fascinating Etruscan culture that once blossomed in the Maremma region. Finally, visit the nearby town of Castiglione della Pescaia, a charming seaside town that offers beautiful beaches and stunning views of the Tyrrhenian Sea.

3 Days In Tuscany– Itinerary For Couples

Tuscany is the perfect romantic getaway for couples, with its picturesque countryside, charming towns, and luxurious accommodations. Take a hot air balloon ride over the rolling hills, sip wine at sunset, and enjoy intimate dinners at local restaurants. Stroll through quaint villages hand in hand, explore historic castles and gardens, or indulge in a couple’s massage at a spa. With its breathtaking scenery and endless opportunities for romance, Tuscany is the perfect destination for couples looking to spend 3 days in Tuscany on a romantic getaway.

Day 1- Siena

visit Tuscany for the first time

Start your day with a visit to the Piazza del Campo, one of the most beautiful squares in Italy, where the famous Palio horse race is held twice a year. Climb the Torre del Mangia, a medieval tower offering stunning views of the city, and enjoy a romantic moment with your partner.

After taking in the breathtaking views, head to the Duomo di Siena, one of the most spectacular Gothic cathedrals in Italy. The cathedral is home to masterpieces by Michelangelo and other renowned artists, and its intricate marble façade is a true work of art.

Later in the afternoon, explore the winding streets of Siena’s historic center, taking in the architecture, browsing shops and boutiques, and stopping for an espresso or a glass of local wine at one of the many charming cafes.

As the sun sets, head to a traditional Tuscan trattoria, such as La Taverna di San Giuseppe, for a romantic candlelit dinner featuring local specialties like ribollita soup and bistecca alla Fiorentina. After dinner, take a stroll around the city, enjoying the romantic atmosphere and the twinkling lights of the medieval buildings.

Day 2- San Gimignano

San Gimignano

Explore the charming town of San Gimignano, known for its beautiful medieval towers and romantic atmosphere. Start your tour at the Piazza della Cisterna, a beautiful square that offers stunning views of the surrounding countryside. Take a leisurely stroll through the narrow streets of San Gimignano and admire the well-preserved medieval architecture. Be sure to visit the town’s two main squares, Piazza del Duomo and Piazza della Cisterna, which are lined with historic buildings and charming cafes.

From there, head to the nearby Osteria Le Cantine for a romantic lunch of local cuisine and wines and don’t forget to try the local gelato (supposedly, Italy’s finest). In the afternoon, head to the Rocca di Montestaffoli, a hilltop fortress that offers panoramic views of the surrounding countryside. Watch the sunset with your partner and enjoy a romantic moment in one of the most beautiful towns in Tuscany.

Day 3- Cortona

cortona tuscany

Start your day with a walk around the town’s historic center. Marvel at the beautiful architecture, narrow streets, and charming piazzas. Don’t miss the Piazza della Repubblica, which is the heart of the town and home to the Palazzo Comunale, the Clock Tower, and the beautiful Gothic-style Duomo di Cortona.

Afterward, head to the Museo dell’Accademia Etrusca to learn more about Cortona’s fascinating Etruscan history. The museum houses a vast collection of Etruscan artifacts, including pottery, jewelry, and sculptures. There are also several rooms dedicated to medieval and Renaissance art.

For lunch, stop at one of the local trattorias and enjoy some delicious Tuscan cuisine. Make sure to try the pici pasta with wild boar ragu or the bistecca alla fiorentina, a famous Florentine steak.

In the afternoon, take a stroll along the town’s ancient walls for breathtaking views of the surrounding countryside. You can also visit the Fortezza Medicea, a 16th-century fortress that offers stunning views of the town.

Finally, end your day with a visit to the beautiful Basilica di Santa Margherita, a 14th-century church that is dedicated to Cortona’s patron saint. The church is known for its beautiful frescoes and peaceful atmosphere.

3 Days In Tuscany– Itinerary For Families

If you’re traveling with your family, you’ll be happy to hear that there are many family-friendly activities you can all enjoy together. Here’s our 3 days in Tuscany itinerary for families.

Day 1- Florence

florence dome

Start your trip in the beautiful city of Florence, known for its art, history, and culture. Start your day early by visiting the iconic Florence Cathedral, also known as the Duomo, with its stunning Renaissance dome designed by Brunelleschi. Climb up to the top of the dome for panoramic views of the city. From there, continue to the Piazza del Duomo, home to the city’s most famous landmarks, including the Cathedral of Santa Maria del Fiore, Giotto’s Campanile, and the Baptistery of St. John.

Next, head to the Uffizi Gallery, one of the most famous art museums in the world. Marvel at masterpieces by Botticelli, Michelangelo, and Leonardo da Vinci, among many others. After lunch, take a stroll across the Ponte Vecchio, the oldest bridge in Florence, lined with shops selling jewelry and other luxury goods.

In the afternoon, visit the Accademia Gallery to see Michelangelo’s famous sculpture, David. Alternatively, explore the fascinating history and architecture of the Palazzo Vecchio, the town hall of Florence.

As the sun sets, climb up to Piazzale Michelangelo for panoramic views of Florence and enjoy a romantic dinner in one of the city’s many trattorias or osterias. Finish the day with a gelato from one of Florence’s famous gelaterias.

Day 2- Pisa

pisa tower italy on a budget

Head to the beautiful town of Pisa, home to the famous Leaning Tower of Pisa. Start your tour at the Piazza dei Miracoli, a beautiful square that houses the tower, the Cathedral of Santa Maria Assunta, and the Baptistery. After lunch, visit the nearby Museo dell’Opera del Duomo, which houses many of the original sculptures from the Piazza dei Miracoli. Complete your day by visiting the Palazzo Blu art museum or the botanical garden, or climb the medieval walls of the city for a panoramic view.

Day 3- Lucca

lucca tuscany

Explore the beautiful town of Lucca, known for its well-preserved Renaissance walls and charming old town. Start your tour at the Piazza dell’Anfiteatro, a beautiful square that was once a Roman amphitheater. From there, head to the nearby Guinigi Tower, a medieval tower with a garden at the top. Finally, visit the nearby Parco Avventura Sospeso nel Verde, an adventure park with zip lines, rope bridges, and other outdoor activities for the whole family.

A Few Other Destinations For Your Tuscany Itinerary


There are plenty of destinations to explore in Tuscany beyond the traditional favorites and there are just too many places to fit in a 3-day itinerary. That’s why we feel it wouldn’t be fair not to mention a few other beautiful places in Tuscany.

Livorno, a port city on the coast, is famous for its seafood, beaches, and historic district. Carrara, located in the Apuan Alps, is famous for its marble quarries, and you can take a guided tour of the quarries or visit the Carrara Marble Museum to learn more about this fascinating material.

Pienza is another beautiful small town in the Val d’Orcia known for its charming streets, beautiful architecture, and excellent pecorino cheese and Cortona is a charming hill station in the province of Arezzo known for its stunning views, charming streets, and Etruscan history.

Finally, Abetone, a ski resort located in the Apennine Mountains, offers stunning views and opportunities for skiing, hiking, and outdoor activities depending on the time of year. All of these destinations offer unique experiences that are well worth exploring during your trip to Tuscany.

How did you like our guide to spending 3 days in Tuscany? Did you get some useful suggestions for your upcoming trip? Did you ever visit Tuscany and if so, what did you like the most? Feel free to share your thoughts in the comments below.

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Thursday 4th of May 2023

Wow, such a comprehensive guide, thank you.

Passport Symphony

Thursday 4th of May 2023

Thank you for the support, Gregg