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.

Castello Vicchiomaggio

@skpaula

A stunning medieval castle offering breathtaking views of the surrounding Chianti countryside, and often hosts cultural events and wine tastings. You can spend the night in this amazing hotel.

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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.

Montefioralle

@skpaula

A picturesque medieval village in the Chianti region, famous for its quaint streets, ancient buildings, and scenic vineyard views. Ideal for a peaceful getaway and wine tasting experiences.

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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.

Castello di Verrazzano

@skpaula

Famous for its winery and vineyards, this castle offers guided tours and wine tastings, allowing visitors to sample some of the region’s finest wines.

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Evening: Explore the town of Greve in Chianti, known for its central square and artisan shops.

Greve in Chianti

@skpaula

A charming town known for its picturesque piazzas, wine tasting opportunities, and the historic Greve Castle.

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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.

Castellina in Chianti

@skpaula

A quaint hilltop town with medieval architecture, offering panoramic views of the Chianti region, and known for its Etruscan roots and wine production.

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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.

Monteriggioni

@skpaula

A perfectly preserved medieval walled town, offering visitors a glimpse into Tuscany’s rich history, with its impressive fortifications and scenic surroundings

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Then head towards the ancient Etruscan town of Volterra, famous for its historic center and alabaster craftsmanship.

Volterra

@skpaula

An ancient hilltop town famous for its well-preserved Etruscan walls, Roman theater ruins, and medieval architecture, as well as its 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.

San Gimignano

@skpaula

Known as the “Medieval Manhattan” for its iconic skyline of medieval towers, this UNESCO World Heritage Site is renowned for its well-preserved medieval architecture and delicious gelato.

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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.

Siena

@skpaula

Discover the timeless beauty of Siena, where medieval streets lead to magnificent palaces and grand churches. From the iconic Piazza del Campo to the majestic Siena Cathedral, immerse yourself in history and culture at every turn in this enchanting Tuscan gem.

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In the afternoon, journey to Montepulciano, famous for its Renaissance architecture and Vino Nobile di Montepulciano wine.

Montepulciano

@skpaula

Perched atop a scenic limestone ridge, Montepulciano is a picturesque Tuscan town renowned for its exquisite Vino Nobile wine and breathtaking views of the surrounding countryside. Wander its ancient streets lined with Renaissance palaces, charming churches, and inviting wine cellars.

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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