Last Updated on December 12, 2025
Tuscany is one of Italy’s most beloved region, celebrated for its rolling hills, medieval towns, world-class art, and unforgettable cuisine. Whether you’re visiting for the first time or returning for another dose of Italian magic, landing at Pisa International Airport (PSA) is the perfect gateway to begin your Tuscan adventure.
If your flight arrives in the morning, before transfer to Siena, you could choose to visit Piazza dei Miracoli, which is home not only to the iconic Leaning Tower, but also to the stunning Duomo and Baptistery.
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A 3–5 day itinerary offers the perfect blend of art, history, countryside, and food.
Siena, Medieval Splendor
Begin your Tuscan journey in Siena, one of Italy’s most well-preserved medieval cities.
Lose yourself in the magical atmosphere of its narrow alleys, wander through the winding streets and arrive and relax at the stunning Piazza del Campo, the heart of the city and site of the famous Palio horse race.
Visit the breathtaking Siena Cathedral (Duomo), with its intricate striped marble interior, and climb the Facciatone for panoramic views. Enjoy dinner in a traditional osteria with local specialties like pici pasta all’aglione or wild boar stew. We stayed in the historic city center to fully immerse ourselves in the experience.
San Gimignano, the Town of Fine Towers
A hilltop town famous for its medieval towers and preserved architecture. Known as the “Medieval Manhattan” of Tuscany. Wander the cobbled streets, climb Torre Grossa for sweeping views of the surrounding vineyards and hills, enjoy some Vernaccia di San Gimignano wine, and don’t miss the famous gelato in Piazza della Cisterna.
Florence, Art, Architecture and the Renaissance
Florence is an open-air museum, offering a blend of majestic art, architecture, and vibrant street life. We visited the Uffizi Gallery home to masterpieces by Botticelli and Da Vinci,the Accademia Gallery and Brunelleschi’s Dome. Don’t miss a walk along the Ponte Vecchio or a visit to the Pitti Palace. Enjoy lunch in the San Lorenzo Market. Florence deserves more than a day, but even in 24 hours, its magic will leave a lasting impression.
For a moment of peace, head to the Boboli Gardens behind Palazzo Pitti, or hike up to Piazzale Michelangelo for the best panoramic view of Florence, especially at sunset.
Beyond the famous landmarks, get lost in the artisan district of Oltrarno, where traditional crafts still thrive. Don’t leave without trying local dishes like lampredotto, or the legendary Florentine steak. Whether you’re a lover of art, history, food, or simply beauty, Florence has something unforgettable to offer.
When to Visit Tuscany
Tuscany is beautiful in every season, but each period offers a different experience depending on your preferences for weather, events, and tourist flow.
- Spring (March to May)
A wonderful time to visit. The countryside comes alive with flowers and greenery, temperatures are mild, and crowds are still manageable. It’s ideal for exploring hill towns, enjoying wine tours, and outdoor activities. - Summer (June to August)
High season. Expect warm to hot temperatures, especially in July and August. This is the busiest time, especially in major cities like Florence and Siena. However, it’s also when many festivals take place, such as Palio di Siena in July and August. - Autumn (September to November)
Arguably the best season for food and wine lovers. The harvest season offers wine festivals, olive oil tastings, and truffle hunts. Weather is still pleasant in September and October, but November can be cooler and quieter. - Winter (December to February)
Low season, with fewer tourists and lower prices. Cities like Florence and Pisa remain lively, but rural areas and smaller towns are quieter. It’s a good time for cultural visits and enjoying local cuisine by the fireplace.
Tips
- Transfers
Especially if you’re traveling during high season or around major events, don’t forget to book experiences, museum tickets, and airport transfers in advance to avoid delays and inconvenience.We have used and thank Pisa Airport Transfers – Italy, with whom we organized all our main transfers in Tuscany, starting from Pisa Airport where we were welcomed by Mario, our first driver! Our flight was even 45 minutes late, but he safely and calmly drove us to Siena, at night, making us feel completely relaxed.
In addition to the other transfers, the return one, from Florence to Pisa Airport, was especially important, and thanks to it we arrived on time for our flight without stress or worries.
- Transfers
- Siena
Visit early morning to enjoy Piazza del Campo without the crowds and see the intricate brickwork up close.
Book a guided tour of the Palazzo Pubblico to understand Siena’s rich medieval history and see frescoes you might otherwise miss.
Don’t just watch the Palio horse race, try to learn about the unique contrada rivalries and history behind the event.
- San Gimignano
Consider staying in agriturismos for an authentic touch.
- Florence
Buy your tickets for major museums like the Uffizi and Accademia in advance to skip long lines.
Visit the Mercato Centrale for fresh local food and an authentic Florentine culinary experience.
Explore hidden gems like the Brancacci Chapel or San Miniato al Monte church for quieter, breathtaking art and architecture.
