5 days (and more) in La Toscana
La Toscana (Tuscany)
Explore the picturesque landscapes and timeless charm of Tuscany's Chianti region on this enchanting itinerary. Immerse yourself in the heart of Italy's wine country as you wander through rolling vineyards, quaint medieval villages, and historic castles. Whether it's savoring a glass of Sangiovese at a family-run winery or admiring the sunset over the vineyard-dotted hills, this journey through Chianti promises unforgettable moments at every turn.
What you will find
- Some basic recommendations
- The proposed 5-day itinerary
- Options for you to expand your stay in Tuscany or even go broader
Basic recommendations
Hotels with charm
- Castello Vechiomaggio
- La Rimbecca
Wine tasting around Chianti
- Castello di Verrazano
- Castello di Querceto
Regional dishes
- Bistecca alla Fiorentina
- homemade pasta (like Picci) al ragú de cinghiale or with truffle
- Cacciucco
- Pappa al pomodoro
And more!
Itinerary
Day 1: Castello Vechiomaggio
Afternoon: Arrive in Florence and take a car to start your journey around La Toscana. Drive to Castello Vechiomaggio which can be your first stay.
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Evening: Spend the evening relaxing at the castle, enjoying the picturesque surroundings and tasting some of their wines (tomorrow you will check the enemy's wine too).
Dinner: If it is on a Friday you might want to try and get a spot in Giulio's table. If not enjoy a quite dinner in the Castello - just lovely.
Day 2: Chianti Tasting
Morning: Start the day with a visit to the charming village of Montefioralle, known for its medieval charm and beautiful views.
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Afternoon & lunch: Take a guided tour, wine tasting and lunch at Castello di Verrazzano, one of the oldest wineries in Chianti, and, as mentioned, the enemy of Castello Vechiomaggio.
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Evening: Explore the town of Greve in Chianti, known for its central square and artisan shops.
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Stay overnight near Castellina in Chianti. We stayed in a very cozy and authentic bed and breakfast that I will be happy to recommend if you contact me.
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I recommend going for dinner to Re Gallo for q bistecca a la Fiorentina and nice wine.
Day 3: San Gimignano & Volterra
Take the car and head to the nearby medieval walled town of Monteriggioni, known for its well-preserved fortifications and panoramic views.
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Then head towards the ancient Etruscan town of Volterra, famous for its historic center and alabaster craftsmanship.
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In the evening, discover the UNESCO World Heritage site of San Gimignano, known for its medieval towers and picturesque streets.
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Return to the same hotel for another night's stay (or not). I am personally a fan of having hotel-hubs so you don’t have to pack and unpack and you have a sense of “home”. However, this is up to you.
This day can be divided into two if you want to relax a bit more.
Day 4: Siena & Montepulciano
Spend the morning exploring the historic city of Siena, known for its stunning cathedral, Piazza del Campo, and Palazzo Pubblico.
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In the afternoon, journey to Montepulciano, famous for its Renaissance architecture and Vino Nobile di Montepulciano wine.
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Enjoy wine tasting at one of the local wineries and explore the town's charming streets and shops.
Return to the same hotel or a new one for the final night's stay.
Day 5: Departure
Check out of the hotel and depart home, or extend your stay in Tuscany to further explore the region's beauty and attractions.
Want to extend your stay?
Tuscany is a huge region and there are tons of little towns and places that are worth visiting.
My first choice would probably be to add Florence as part of your trip if you have not visited it yet. If not, maybe spending 2 more days in Tuscany and finishing with 2 day in Rome can be a great oportunity. However, you can also link Tuscany with Pisa and Cinque Terre. The options are infinite - it depends on what you want and the time you have.
Therefore, let's me just name some of the most beautiful towns and places focusing on Tuscany, taking Siena as the southernmost-point visited and Volterra as the northernmost-point.
If you head south (which would be my first choice), I would recommend visiting:
- Montalcino
- Pienza
- San Quirico d’Orcia
- Bagno Vignoni
(…)
If you head north, I would recommend visiting:
- Lucca
- Colle di Val d’Elsa
(…)
As said, you can always mix this with:
- Days in Florence
- Days in Rome
- A day in Pisa
- Some days around Cinque Terre
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