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7-Day Scenic Tuscany Road Trip: Exploring Tuscany’s Iconic Landscapes and Culinary Delights

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Day 1: Florence Arrival

Florence, Italy on May 1, 2025

9:00am

Breakfast at Caffè Gilli

Enjoy a traditional Italian breakfast with fresh pastries and espresso at this historic café located in Piazza della Repubblica.
EUR8, 0h45m

10:00am

Uffizi Gallery

Visit the renowned Uffizi Gallery to view masterpieces of Renaissance art by Botticelli, Michelangelo, and Leonardo da Vinci.
EUR20, 2h30m

1:00pm

Lunch at Trattoria Mario

Dine at this beloved Florentine trattoria serving authentic Tuscan cuisine in a casual setting.
EUR25, 1h15m

3:00pm

Ponte Vecchio and Historic Center Walk

Stroll across the iconic Ponte Vecchio and explore Florence’s historical center including Piazza della Signoria.
Free, 1h30m

6:00pm

Dinner at La Giostra

Savor elegant Tuscan dishes and renowned bistecca alla Fiorentina in an intimate atmosphere.
EUR50, 2h
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Day 2: Chianti Wine Region

Chianti, Tuscany, Italy on May 2, 2025

8:30am

Breakfast at Hotel

Start with a hearty Italian breakfast at your hotel before heading out to the countryside.
Included, 0h45m

10:00am

Castello di Brolio Wine Tour

Tour the historic Castello di Brolio estate and enjoy a wine tasting experience featuring Chianti Classico wines.
EUR30, 2h

1:00pm

Lunch at Osteria Le Panzanelle

Enjoy rustic Tuscan dishes accompanied by local wine in a charming setting in the heart of Chianti.
EUR30, 1h30m

3:00pm

Drive through Chianti Hills

Take a scenic drive through rolling vineyards and olive groves, stopping for photos and short walks.
Free, 2h

7:00pm

Dinner at Ristoro di Lamole

Dine in perched terrace restaurant with views over the Tuscan countryside, offering local specialties.
EUR40, 2h
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Day 3: Medieval Siena

Siena, Tuscany, Italy on May 3, 2025

8:00am

Breakfast at Pasticceria Nannini

Taste Siena’s famous cantucci biscuits with morning coffee at this historic bakery.
EUR10, 0h45m

9:30am

Piazza del Campo & Torre del Mangia

Explore Siena’s stunning main square and climb the Torre del Mangia for panoramic views.
EUR15, 2h

12:00pm

Siena Cathedral (Duomo di Siena)

Visit the striking black-and-white marble cathedral with intricate frescoes and sculptures.
EUR12, 1h

1:30pm

Lunch at Antica Trattoria Papei

Enjoy traditional Tuscan fare with a local ambiance near the historic center.
EUR30, 1h30m

3:30pm

Wander Medieval Streets

Spend the afternoon discovering small shops, and historic churches, and savoring gelato.
Free, 2h

7:00pm

Dinner at La Taverna di San Giuseppe

Dine on refined Tuscan cuisine in a cozy medieval cellar setting.
EUR45, 2h
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Day 4: Val d'Orcia Landscapes

Pienza & Montalcino, Tuscany, Italy on May 4, 2025

7:30am

Breakfast at Hotel

Fuel up for the day with a buffet breakfast at your accommodation.
Included, 0h45m

9:00am

Pienza Town Walk

Explore this Renaissance town known for its pecorino cheese and panoramic views of the Val d'Orcia.
Free, 1h30m

11:00am

Visit to Pecorino Cheese Farm

Tour a local farm to see cheese production and taste fresh pecorino varieties.
EUR20, 1h

12:30pm

Lunch at La Bandita Townhouse

Enjoy a lunch of modern Tuscan cuisine in a stylish setting in Pienza.
EUR35, 1h30m

3:00pm

Montalcino & Brunello Wine Tasting

Drive to Montalcino for wine tasting at a renowned Brunello winery such as Castello Banfi.
EUR40, 2h

7:30pm

Dinner at Osteria Le Potazzine

Dine on organic, locally sourced dishes paired with excellent Brunello wines.
EUR50, 2h
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Day 5: Montepulciano and Surrounds

Montepulciano, Tuscany, Italy on May 5, 2025

8:00am

Breakfast at Bar Il Teatro

Enjoy coffee and fresh pastries in Montepulciano’s historic center.
EUR8, 0h45m

9:30am

Montepulciano Town Tour

Walk the medieval streets and visit Piazza Grande and the Cathedral.
Free, 1h30m

11:00am

Wine Cellar Tour & Tasting

Visit one of Montepulciano’s famous wine cellars to learn about and taste Vino Nobile di Montepulciano.
EUR25, 1h30m

1:00pm

Lunch at La Grotta

Savor traditional dishes in a grotto-style restaurant right in the town center.
EUR30, 1h30m

3:00pm

Drive to San Quirico d’Orcia

Visit this charming village, known for its Horti Leonini gardens and historic architecture.
Free, 1h30m

6:00pm

Dinner at Ristorante Il Falcone

Enjoy elegant Tuscan fare with beautiful views of the Val d’Orcia countryside.
EUR45, 2h
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Day 6: San Gimignano & Countryside

San Gimignano, Tuscany, Italy on May 6, 2025

8:00am

Breakfast at Bar San Francesco

Start your day with cappuccino and pastries at this lively local café.
EUR7, 0h45m

9:00am

Explore San Gimignano Historic Center

Wander through this UNESCO medieval town known for its towers, museums, and artisan shops.
EUR10, 2h

11:30am

Gelateria Dondoli

Taste award-winning gelato in a picturesque town square setting.
EUR5, 0h30m

12:00pm

Lunch at Cum Quibus

Treat yourself to creative Tuscan dishes made from fresh local ingredients.
EUR40, 1h30m

2:00pm

Villa La Foce Gardens

Visit the magnificent gardens overlooking Val d’Orcia, open from 10am to 5pm.
EUR15, 1h30m

6:00pm

Dinner at La Mandragola

Enjoy a relaxed meal with countryside views and traditional Tuscan dishes.
EUR35, 2h
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Day 7: Return to Florence

Florence, Italy on May 7, 2025

8:00am

Breakfast at Hotel

Prepare for the return trip with a leisurely breakfast.
Included, 0h45m

10:00am

Drive back to Florence

Scenic drive north through the Tuscan countryside heading back to Florence, about 1.5 to 2 hours drive.
Fuel costs approx EUR20, 2h

12:30pm

Lunch at Mercato Centrale

Sample diverse Tuscan street foods and fresh local products at Florence’s central market.
EUR15, 1h

2:00pm

Boboli Gardens

Relax and stroll through the expansive Boboli Gardens behind Pitti Palace, open until 7pm.
EUR10, 1h30m

5:00pm

Evening Stroll and Final Aperitivo

End your trip with an evening walk around the Arno River and sip an aperitivo at La Terrazza Rooftop Bar.
EUR15, 2h
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