Only have a weekend to discover Tuscany? No problem! In this article, you’ll find a complete 3-day itinerary designed to immerse you in the region’s beauty: art, nature, delicious food, historic villages, and unforgettable views. From the Renaissance charm of Florence to the rolling hills of Chianti and the medieval poetry of Siena, this route takes you to the heart of authentic Tuscany. At the end, you’ll discover the best way to enjoy it all stress-free with a tailor-made private tour.
Day 1: Florence – Art, History, and Hidden Views
Morning
- Start at the Florence Cathedral: visit Santa Maria del Fiore and climb Brunelleschi’s Dome (booking required) for a breathtaking view of the city.
- Walk through Piazza della Signoria: admire Palazzo Vecchio and the statues under the Loggia dei Lanzi.
- Uffizi Gallery: if you love art, this museum is a must-see (book in advance!).
Recommended lunch: Trattoria Cammillo or I’Brindellone for authentic Florentine cuisine.
Afternoon
- Oltrarno and artisans: cross Ponte Vecchio and explore workshops on Via Maggio and in Santo Spirito.
- Boboli Gardens or Bardini Gardens: relax and enjoy stunning views.
- Oblate Library terrace: have a sunset coffee with a direct view of the Dome.
Evening
- Dinner with a view at one of the panoramic terraces (e.g. La Loggia or SE.STO on Arno).
- Romantic stroll along the Arno and maybe a gelato from Gelateria dei Neri.
Day 2: Chianti – Medieval Villages, Vineyards, and Castles
Morning
- Drive from Florence to Greve in Chianti (about 50 mins).
- Visit the Market Square and the Wine Museum.
- Wine tasting at a historic winery (e.g. Castello di Verrazzano or Montefioralle Winery).
Tip: If you have a driver or private NCC, you can enjoy the wines stress-free.
Lunch in a farmhouse with views over the hills.
Afternoon
- Continue to Radda in Chianti and Castellina in Chianti: charming villages with ancient walls, wine shops, and panoramic views.
- If you love castles, visit Castello di Brolio, residence of the Ricasoli Barons.
Evening
- Return to Florence or overnight stay in a relais among the vineyards.
- Dinner at your accommodation or at a typical restaurant like “La Cantinetta di Rignana”.
Day 3: Siena and the Val d’Orcia – History and Postcard Landscapes
Morning
- Early departure to Siena (about 1h20).
- Visit Piazza del Campo, the Cathedral, and the Piccolomini Library.
- Walk through the historic districts known as “contrade”.
Typical lunch: Enjoy pici cacio e pepe or ribollita at restaurants like Osteria Le Logge.
Afternoon
- Head towards the Val d’Orcia: stop at Pienza (cheese and views), San Quirico d’Orcia, and maybe a photo stop at the Chapel of Madonna di Vitaleta.
- If time allows, take a relaxing bath at Bagno Vignoni hot springs.
Evening
- Sunset aperitivo on a terrace in Pienza or Montalcino.
- Dinner with Brunello di Montalcino, then either stay overnight or return to Florence.
Practical Tips for a Perfect Weekend in Tuscany
- Getting around: a car is useful, but with an NCC (private driver), the journey is more relaxed and flexible.
- Best time to visit: April–June and September–October offer ideal weather and fewer crowds.
- What to pack: comfortable shoes, sunglasses, camera, and a sense of wonder.
- Reservations: book museums, wineries, and restaurants in advance, especially on weekends.
Experience Tuscany in a Weekend with Tuscany Private Tours
With limited time, every moment counts. That’s why having a knowledgeable local guide makes all the difference. With Tuscany Private Tours, the private driver and guided tour service by Maurizio Bellini, you can:
- Get a custom itinerary tailored to your interests
- Travel in total comfort with a private chauffeur
- Access authentic and lesser-known experiences
- Optimize your time without sacrificing quality
Visit tuscanyprivatetours.net and plan your weekend in Tuscany like a true insider
