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Family Friendly Siena Countryside Getaway

Viewed by 56 travelers

Day 1: City Center Exploration

Siena, Italy

9:00AM

Breakfast at Pasticceria Nannini

Start your day with delicious pastries and coffee at this charming local bakery.
€10, 1 hour

10:30AM

Visit Piazza del Campo

Take a leisurely stroll around the iconic square, and marvel at the stunning architecture of the Palazzo Pubblico.
Free, 1.5 hours

12:30PM

Lunch at Osteria La Piana

Enjoy a traditional Tuscan lunch with the family at this cosy trattoria, known for its authentic local cuisine.
€15 per person, 1.5 hours

2:30PM

Explore the Siena Cathedral

Admire the beautiful architecture and intricate designs of this historic cathedral, a UNESCO World Heritage site.
€8, 1 hour

4:00PM

Relax at Villa Borghese Public Gardens

Unwind in the peaceful surroundings of the gardens, perfect for a leisurely family walk or a restful break.
Free, 1 hour

7:00PM

Dinner at Trattoria La Torre

Indulge in a delightful dinner featuring Tuscan specialties at this family-friendly restaurant with a cosy atmosphere.
€20 per person, 2 hours
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Day 2: Chianti Countryside

Chianti, Italy

9:00AM

Breakfast at Bar-Pasticceria Il Bandino

Start your day with a hearty breakfast of pastries and cappuccino at this local favourite.
€8, 1 hour

10:30AM

Visit Castello di Brolio

Explore the historic castle and its beautiful gardens, with stunning views of the Chianti countryside.
€12, 2 hours

1:00PM

Lunch at Ristorante Malborghetto

Enjoy a leisurely lunch at this charming countryside restaurant, offering delicious Tuscan dishes and local wines.
€18 per person, 1.5 hours

3:00PM

Wine Tasting at Fattoria di Montemaggio

Relax and enjoy a family-friendly wine tasting experience at this picturesque winery, surrounded by vineyards and rolling hills.
€10 per person, 1.5 hours

5:00PM

Scenic Drive through Chianti Countryside

Take a leisurely drive through the picturesque Chianti region, soaking in the breathtaking views of vineyards and olive groves.
Free, 2 hours

7:30PM

Dinner at Osteria Castelvecchio

End your day with a delightful dinner at this charming restaurant, known for its warm hospitality and delectable Tuscan cuisine.
€20 per person, 2 hours
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More About Siena, italy

Trip Packing List: Italy (Florence/Siena/Pisa/Lucca) + 1 night London — March 16–20, 2026
Packing List
8-Day Italy: Rome (2), Pompeii (1), Florence (1 + base), Venice (1), Pisa (1), Siena & San Gimignano (1)
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Itinerary created by AI-assisted, human-reviewed

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