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3-Day Scenic Tour from Siena to the Chianti Region: Wine, Villages & Tuscan Charm

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Day 1: Siena to Castellina

Siena to Castellina in Chianti, Italy on April 25, 2025

8:00am

Breakfast at La Prosciutteria, Siena

Start your day with a delicious Italian breakfast featuring fresh pastries and strong espresso at this popular deli and café. Opens at 8:00am.
EUR8, 0h30m

9:00am

Explore Piazza del Campo, Siena

Stroll around Siena's historic heratage core and admire the stunning shell-shaped square and the medieval architecture that surrounds it.
Free, 1h

10:30am

Drive to Castellina in Chianti

Enjoy a scenic 40-minute drive through Tuscan countryside headed toward Castellina, a charming town in Chianti known for its vineyards and Etruscan history.
EUR0, 0h40m

11:30am

Visit Rocca di Castellina

Explore this medieval fortress with panoramic views across the Chianti vineyards. The site highlights the history and culture of the area.
EUR5, 1h

12:45pm

Lunch at La Bottega di Giovannino

Savor authentic Tuscan dishes paired with Chianti wines at this cozy trattoria located in the heart of Castellina. Open midday for lunch.
EUR25, 1h15m

2:00pm

Chianti Classico Wine Tasting at Castello di Verrazzano

Visit this renowned winery for a guided tasting tour that includes cellar exploration and sampling Chianti Classico wines. Open 10am–6pm.
EUR20, 1h30m

4:00pm

Check in at local agriturismo accommodation

Relax and enjoy the peaceful countryside setting before dinner. Options available include agriturismos offering scenic views and Tuscan hospitality.
Variable, N/A

7:30pm

Dinner at Ristorante Oltre il Giardino

Dine on Tuscan specialties with fresh, local ingredients paired with excellent Chianti wines in a charming garden setting.
EUR40, 1h30m
Find Hotels in Siena to Castellina in Chianti

Day 2: Villages & Wine

Castellina to Greve in Chianti, Italy on April 26, 2025

8:00am

Breakfast at accommodation

Enjoy a traditional Tuscan breakfast with fresh bread, local jams, and coffee to start your day.
Included, 0h30m

9:00am

Drive to Greve in Chianti

A short 30-minute drive takes you to Greve, a vibrant market town that is the gateway to Chianti wine country.
EUR0, 0h30m

9:45am

Visit Piazza Matteotti & Local Market

Explore the triangular square surrounded by cafés and shops. Enjoy the lively local market (held Saturdays) for Tuscan products.
Free, 1h

11:00am

Wine Tasting at Castello di Montefioralle

Tour this picturesque winery and historic village onsite with tastings of Chianti Classico varieties. Open from 10am.
EUR15, 1h30m

1:00pm

Lunch at Enoteca Falorni

Dine on local specialties and extensive Chianti wines at this renowned enoteca famous throughout Tuscany.
EUR30, 1h15m

2:30pm

Visit Greve Wine Museum

Learn about Chianti's winemaking traditions and history at this small but informative museum in Greve. Open until 6pm.
EUR5, 1h

4:00pm

Leisurely walk to surrounding vineyards or visit La Pesa winery

Enjoy a stroll through the scenic vineyards nearby or schedule a visit/tasting at La Pesa, open in the afternoon.
Variable, 1h

7:30pm

Dinner at Trattoria da Tito

Experience warm hospitality and classic Tuscan dishes in Greve’s traditional trattoria favored by locals.
EUR35, 1h30m
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Day 3: Radda & Return

Greve to Radda in Chianti, Italy then back to Siena on April 27, 2025

8:00am

Breakfast at accommodation in Greve

Fuel up with a light Tuscan breakfast at your lodging before heading out to Radda.
Included, 0h30m

9:00am

Drive to Radda in Chianti

A scenic 30-minute drive brings you to Radda, known for its medieval charm and peaceful vistas over vineyards.
EUR0, 0h30m

9:45am

Visit Radda’s Historic Center

Wander cobblestone streets and medieval walls, visiting small shops and galleries in this authentic Tuscan town.
Free, 1h

11:00am

Castello di Radda Wine Tasting

Enjoy an uplifting tasting session at one of Radda’s notable wineries specializing in Chianti Classico. Open mid-morning to early afternoon.
EUR20, 1h

12:30pm

Lunch at La Bottega di Volpaia (on route back)

Stop for a delicious lunch in Volpaia, a picturesque village with excellent farm-to-table dining options, open around noon.
EUR30, 1h15m

2:00pm

Drive back to Siena

Return to Siena with beautiful views of the Chianti hills, ending your memorable trip after an approximate 45-minute drive.
EUR0, 0h45m
Find Hotels in Greve to Radda in Chianti
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