There are so many Tuscany tours to choose from to explore this region of Italy. From feeling the wind in your hair on a guided vespa tour to relaxing with a glass of Brunello di Montalcino while looking out at the wine region in Montalcino, Tuscany offers wonderful experiences full of majestic views and incredible memories.
Tuscany has a deep history full of rich culture. The best way to truly get to know this amazing Italian region is to explore with a local. Joining a guided tour is an amazing way to get to know Tuscany on a deeper level, whether you choose to join one of the many Tuscany tours, exploring by bike or vespa, or immersing yourself in the cuisine or wine.
I’ve put together some of the best tours in Tuscany. Keep reading to see how I would spend seven days in Tuscany, along with some of the best tour options and the highlights of exploring the Italian countryside.
Day 1, 2 – Florence
Your first two days in Tuscany will be spent in Florence, the heart of Renaissance art culture. During your time in Florence, dive into the art scene by visiting the Uffizi Gallery, home to works of art by Botticello, Leonardo da Vinco, and Michelangelo. You can wander the streets, getting to stumble upon Florence’s Duomo and the Ponte Vecchio. Indulge in authentic Tuscan cuisine such as the famous Florentine steak or try a ribollita, which is a savory vegetable soup. Italy is known for their gelato, and Florence has some of the best.
Insider Tip: Try a traditional flavor like pistachio or stracciatella or a newer flavor like lavender.
Day 3 – Siena and Val d’Orcia
On your 3rd day in Tuscany you will head to Siena and Val d’Orcia. Siena is a captivating town full of medieval charm. Highlights include the Siena Cathedral and the Palazzo Pubblico. Make sure you explore the 13th century Italian Gothic architecture by climbing to the top of the Torre del Mangia for incredible views over the city. From Siena, Tuscany tours will head to Val d’Orcia, which is one of the most beautiful areas in the region. Make sure to stop at the picturesque Cappella di Vitaleta, a popular church for photos, Bosco di Cipressi which is a photogenic group of Cyprus trees, and Bagno Vignoni, a quaint town famous for its thermal hot springs.
Insider Tip: Try the local Pecorino cheese in Val d’Orcia. Visit a local cheese shop or dairy farm to try the freshest version of this local specialty.
Day 4 – Pitigliano and Saturnia
Pitgliano is nicknamed the “Little Jerusalem” thanks to its ancient Jewish history. Perched on top of tufa cliffs, the narrow cobblestone streets create a unique atmosphere to the charming town. Stop by the Orsini Palace and explore the Renaissance palace while learning about Pitgliano’s history. You should also go to the Vie Cave and the Cathedral of Saints Peter and Paul. stop at a local trattoria for lunch for handmade pasta and a glass of local wine. In Saturnia, stop at the neutral thermal springs surrounded by the picturesque countryside. Spend the evening exploring the quaint town center strolling through the Italian alleyways and enjoying a leisurely dinner at a local restaurant.
Insider Tip: The thermal springs provide a unique photo opportunity, bring a waterproof phone case to be able to capture your experience at the Cascate del Mulino.
Day 5 – Maremma
Start your day in Maremma by visiting the capital of Grosseto. Explore the Medicean Walls surrounding the historic center, stop at a local cafe for a cappuccino and a pastry, and head to the Parco Naturale della Maremma. Here you can choose to take a guided hike or explore by horseback through the park’s beautiful coastal landscape. Surrounded by pine forests and sandy beaches, the landscape is equally as peaceful as it is stunning. Visit a coastal town like Castiglione della Pescaia for a delicious lunch of fresh seafood.
Insider Tip: For dinner, try a traditional Maremman dish like acquacotta or wild boar stew.
Day 6 – Pisa
A day in Pisa during Tuscany tours allows you to explore many attractions in the city, including the iconic Leaning Tower of Pisa. Arrive at Piazza dei Miracoli early to see the Leaning Tower of Pisa without the crowds, and then explore the Duomo and the Battistero to see the stunning Romanesque architecture. Try a traditional fish like pappa al pomodoro, which is a delicious soup made of tomato and bread. After lunch, visit the lively Borgo Stretto to do some shopping and people watching before checking out the Church of Santa Maria della Spina, a gothic church known for its intricate facade along the Arno River.
Insider Tip: Take a relaxing walk along the Arno River at night, admiring the illuminated buildings and the serenity of Pisa by night.
Day 7 – Lucca and Florence
Lucca is a charming town with a relaxed atmosphere full of history. A popular activity in the town is renting a bicycle and exploring the Renaissance walls by bike. This is an amazing way to see an overview of Lucca. You can bike to the Piazza dell’Anfiteatro which is a square that used to host ancient Roman gladiator games. Head to the Cathedral of San Martino to climb the bell tower and see the panoramic views of Lucca as well as the Romanesque architecture. Finish your week by heading back to Florence and having one last dinner in Tuscany.
Insider Tip: Make sure you venture out of the main streets and squares in Lucca to discover local shops, cafes, and artisan studios.
Read More: How many days in Tuscany?
Montalcino is a small medieval town located on top of a hill in the south of Tuscany. Its most famous wine is the Brunello di Montalcino, one of Italy’s most prestigious wines. It is made of 100% Sangiovese grapes grown in the region. It has a deep ruby-red color and has a complex flavor mixture of dark cherry, blackberry, and plum. Brunello di Montalcino is often paired with hearty Italian dishes like osso buco or aged cheeses. When on a wine tour of Montalcino, you can expect to try multiple different Montalcino wines, either a lunch of snacks consisting of local dishes and ingredients, and the opportunity to relax and take in the views over the Tuscan countryside. Montalcino is a fantastic town to visit on its own, or you can choose to take a Tuscany wine tour from Florence to visit the charming town and its incredible wineries.
Book now: wine tour from of Montalcino
When in Montepulciano, join one of the many Tuscany wine tours in the region, getting the opportunity to explore a local winery and get a feel for the history of local winemaking. Montepulciano is known for the production of Vino Nobile di Montepulciano, which is one of Italy’s oldest and most esteemed red wines. The town has a winemaking history which dates back to Etruscan era and was granted DOCG (Denominazione di Origine Controllate e Garantita, which is one of the highest classifications for Italian wines) in 1980. One of the most notable factors about this wine is its aging process, which is legally required to be at least two years in oak barrels and two months in the bottle. During Tuscany tours in Montepulciano you will get to explore historic wineries, tasting Vino Nobile wines, and gaining a deeper understanding of the complex winemaking heritage of the town. Montepulciano is a must visit destination for wine enthusiasts.
Book now: wine tour from Montepulciano
Wine tours in Chianti offer an incredible experience exploring one of Italy’s most famous wine regions. Chianti is known for its spectacular wines, specializing in Chianti Classico. The Chianti Classico was one of the first wines to be granted the DOCG award. Chianti has a deep flavor with characteristics that may include cherry, plum, red berry aromas, and hints of violet and earthy undertones. Chianti goes best with classic Tuscan dishes such as tomato-based sauces, grilled meats, and aged pecorino cheese. During a wine tour in Chianti, you can enjoy tastings of the Chianti Classico paired with breads and cheeses and the incredible views over the Tuscan landscapes.
Book now: wine tour from Chianti
You will love exploring the historic city of Siena on a bike tour. Biking through the beautiful surroundings and charming town, you will get to experience a unique side of Siena while discovering the rich history and pedaling through the amazing medieval architecture. You will get to bike through the one of a kind Tuscan countryside, through the many vineyards, the rolling hills, and the picturesque olive groves. Many Tuscany tours in Siena will take you to local wineries, giving you the opportunity to learn about the history of winemaking in the region, letting you try local wines, and providing snacks or lunch to enjoy the day with.
Book now: Siena bike tour
Lucca is famous for its well-preserved Ressaisance walls, its historic city center, and the charming atmosphere of the town. Many people choose to explore the historic wall surrounding the city by bike, giving you a unique perspective of the city. You can choose between Lucca bike tour of a leisurely city tour exploring the historic center or take an extensive tour into the countryside of Tuscany. Many tours offer a culinary experience, including stopping at local wineries or traditional Tuscan restaurants for tastings of regional wines and cuisine.
Book now: Lucca bike tour
Maremma is one of the most beautiful towns in the region and joining a Tuscany bike tour here will be a highlight of your trip. The Maremma region is famous for its beautiful landscape, offering stunning views of the coastline. There are many nature parks in the region, including the Maremma Regional Park and the Diaccia Botrona Nature Reserve. Bike tours through Maremma allow you to ride through diverse landscapes taking in the natural beauty of Tuscany. Full of history, you will get the opportunity to learn about the fascinating Etruscan heritage and the culture of the region. You can really immerse yourself in the region’s culture here by visiting Etruscan archaeological sites, historic villages, and local artisan workshops. There are many Tuscany tours in Maremma that include the opportunity to bike to local wineries, trying local wines and pairing them with traditional Tuscan cuisine.
Book now: Maremma bike tour
Tuscany Vespa Tours
Riding a Vespa through the rolling hills of Tuscany is an iconic and thrilling experience. The Vespa is an iconic symbol of Italian culture and taking in the scenic landscapes with the wind against you will be a highlight of your trip to Italy. During Tuscany Vespa tours, you are able to visit all of the hidden gems in the region that may not be accessible via car or train, exploring vineyards, olive groves, and cypress lined roads. Vespa tours will be guided by locals who know the region well, they will provide you insights about local history, culture, and traditions. Exploring the scenic route, you may also stop at a local trattoria for lunch to make your Tuscan well rounded with a classic dish paired with Tuscan wine.
Book now: Tuscany Vespa tours
Tuscany Food Tour
Tuscany is home to some of the best food in Italy. Joining a Tuscany food tour will be a highlight of your trip as you indulge in dishes like bruschetta, ribollita, and pappardelle al toscano. Visit historical hill towns like Pienza, Montalcino, and Montepulciano and experience a true farm to table experience. Many Tuscany tours pride themselves in letting visitors witness the production of olive oil, wine, cheese, and other local products before trying them. Some Tuscan food tours will include a cooking class, truffle hunting, or exploring local markets with a local to find the freshest ingredients. Tuscan staples include extra virgin olive oil, aged cheese like pecorino, and cured meats like prosciutto and salami.
Start planning your trip now: Airports in Tuscany