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Family Friendly Siena Itinerary

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Day 1: Explore Siena

Siena, Italy

8:00AM

Breakfast at Bar Pasticceria Nannini

Start your day with delicious pastries and coffee at Bar Pasticceria Nannini, a local favorite in Siena.
Bar Pasticceria Nannini is located in the heart of Siena, you can walk there from most accommodations.
EUR 10, 1 hour

10:00AM

Visit Siena Cathedral

Explore the stunning Siena Cathedral with its intricate marble facade and beautiful interior. Don't miss the Piccolomini Library inside.
Siena Cathedral is a short walk from Bar Pasticceria Nannini.
EUR 15, 2 hours

1:00PM

Lunch at Osteria Le Logge

Enjoy authentic Tuscan cuisine at Osteria Le Logge, known for its delicious pasta dishes and local wines.
Osteria Le Logge is located near Piazza del Campo.
EUR 20, 1.5 hours

3:00PM

Walk around Piazza del Campo

Stroll around Siena's main square, Piazza del Campo, and marvel at the historic Palazzo Pubblico and Torre del Mangia.
Piazza del Campo is a short walk from Osteria Le Logge.
Free, 1 hour

5:00PM

Gelato at Gelateria di Piazza

Indulge in some of the best gelato in Siena at Gelateria di Piazza, a local favorite with unique flavors.
Gelateria di Piazza is near the cathedral.
EUR 5, 30 minutes

6:00PM

Dinner at Antica Osteria da Divo

End the day with a delicious dinner at Antica Osteria da Divo, offering traditional Tuscan dishes in a cozy atmosphere.
Antica Osteria da Divo is located in the historic center of Siena.
EUR 30, 2 hours
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Day 2: Day Trip to San Gimignano

San Gimignano, Italy

8:00AM

Breakfast at Gelateria Dondoli

Start your day with a refreshing breakfast at Gelateria Dondoli, known for its award-winning gelato and coffee.
Gelateria Dondoli is located in the center of San Gimignano.
EUR 10, 1 hour

10:00AM

Explore San Gimignano's Towers

Visit the iconic medieval towers of San Gimignano and enjoy panoramic views of the Tuscan countryside from above.
The towers are scattered throughout the town and can be easily explored on foot.
EUR 9, 2 hours

1:00PM

Lunch at Ristorante Dorando

Have a leisurely lunch at Ristorante Dorando, a charming restaurant offering Tuscan specialties with a view.
Ristorante Dorando is located near the town center.
EUR 25, 1.5 hours

3:00PM

Wine Tasting at Rocca di Castagnoli

Experience a wine tasting at Rocca di Castagnoli, a renowned winery in the region known for its Chianti Classico wines.
Rocca di Castagnoli is a short drive from San Gimignano.
EUR 20, 1 hour

5:00PM

Return to Siena

Head back to Siena and relax at your accommodation after a day of exploring San Gimignano.
Drive back to Siena for an evening of rest.
Gas cost, 1.5 hours

7:00PM

Dinner at Ristorante Le Campane

Enjoy a delicious dinner at Ristorante Le Campane, known for its authentic Tuscan dishes and warm hospitality.
Ristorante Le Campane is located in the heart of Siena.
EUR 30, 2 hours
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Day 3: Visit Pienza and Montepulciano

Pienza and Montepulciano, Italy

8:00AM

Breakfast at Caffè Poliziano

Start your day with a tasty breakfast at Caffè Poliziano, a charming cafe in Montepulciano known for its pastries and coffee.
Caffè Poliziano is located in the town center of Montepulciano.
EUR 10, 1 hour
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Day 4: Relax at Terme di Saturnia

Saturnia, Italy

8:00AM

Breakfast at Bar Eden

Start your day with a light breakfast at Bar Eden, offering a selection of pastries and coffee in Saturnia.
Bar Eden is located in the town center of Saturnia.
EUR 5, 1 hour
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Day 5: Discover Florence

Florence, Italy

8:00AM

Breakfast at Le Vespe Café

Kickstart your day with a delicious breakfast at Le Vespe Café, a popular spot in Florence known for its pastries and coffee.
Le Vespe Café is centrally located in Florence, near the Duomo.
EUR 10, 1 hour
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Day 6: Enjoy Chianti Region

Chianti Region, Italy

8:00AM

Breakfast at La Bottega Del Nobile

Start the day with a hearty breakfast at La Bottega Del Nobile, a cozy cafe in the Chianti region offering local specialties.
La Bottega Del Nobile is located in the town center of Chianti.
EUR 15, 1 hour
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Day 7: Siena Gardens and Parks

Siena, Italy

8:00AM

Breakfast at Bar il Lumiere

Begin the day with a relaxing breakfast at Bar il Lumiere, a charming cafe near the gardens in Siena.
Bar il Lumiere is a short walk from the main gardens in Siena.
EUR 10, 1 hour
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More About Siena

Trip Packing List: Italy (Florence/Siena/Pisa/Lucca) + 1 night London — March 16–20, 2026
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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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