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5-day Trip to Florence, Siena, and San Gimignano

5-day Trip to Florence, Siena, and San Gimignano Itinerary

Last updated: 2024 Jun 14

Exploring the Beauty of Florence

Morning
Start your day with a delicious breakfast at Trattoria La Casalinga to fuel up for a day of exploration. Afterward, visit the iconic Basilica of Santa Maria Assunta (Duomo di San Gimignano) and admire its stunning architecture.
Afternoon
Enjoy a leisurely walk through the historical center of Florence and visit the renowned Florence Balloon Flight Over Tuscany for a breathtaking aerial view of the city. For lunch, head to Il Latini and indulge in traditional Tuscan cuisine.
Evening
Experience the vibrant nightlife of Florence by dining at All'Antico Vinaio, a popular sandwich shop, and then enjoy a drink at Perseus, a cozy bar known for its craft cocktails.
Bedtime
Find amazing hotels in Florence, Italy.
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Basilica of Santa Maria Assunta (Duomo di San Gimignano)

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Florence Balloon Flight Over Tuscany

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Art and Culture in Florence

Morning
Start your day with a visit to the world-famous Uffizi Gallery to admire masterpieces by artists such as Botticelli and Michelangelo. Afterward, enjoy a coffee at Caffè Gilli, a historic café in the heart of Florence.
Afternoon
Explore the historic Ponte Vecchio and its surrounding area, known for its unique shops and jewelry stores. For lunch, savor traditional Tuscan dishes at Ristorante Buca Mario.
Evening
Immerse yourself in the local atmosphere by dining at Trattoria I'Brindellone, a traditional trattoria, and then enjoy a live music performance at Jazz Club Firenze.
Bedtime
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Uffizi Gallery

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Jazz Club Firenze

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Discovering the Charm of Siena

Morning
Take a day trip to Siena and start your morning with a guided walking tour of the city, including a visit to the Siena Cathedral and the Piccolomini Library. Enjoy a delicious lunch at Osteria delle Tre Panche, known for its authentic Tuscan cuisine.
Afternoon
Explore the medieval streets of Siena and visit the Basilica of San Domenico. For a unique experience, take part in a Siena Contrada Museum Visit to learn about the city's historic neighborhoods. Enjoy a snack at La Cantinetta Wine Bar, known for its selection of local wines.
Evening
Indulge in a traditional Tuscan dinner at La Giostra, a renowned restaurant known for its romantic atmosphere and delicious cuisine.
Bedtime
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Siena Cathedral

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Piccolomini Library

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Wine Tasting in San Gimignano

Morning
Travel to San Gimignano and start your day with a visit to a local winery for a San Gimignano Vineyard and Cellar Tour with Wine Tasting. Enjoy the beautiful vineyards and taste the region's finest wines. For lunch, savor Tuscan specialties at Osteria Cipolla Rossa.
Afternoon
Explore the charming medieval town of San Gimignano and visit the Museo Civico e Torre Grossa for panoramic views of the surrounding countryside. For a unique dining experience, enjoy a meal at Borgo Antico, a restaurant located in a historic building.
Evening
End your day with a relaxing dinner at Osteria Santo Spirito, known for its cozy atmosphere and traditional Tuscan dishes.
Bedtime
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Farewell to Florence

Morning
Take a guided tour of the Basilica di Santa Croce, the final resting place of many renowned Italian figures. Enjoy a leisurely breakfast at Trattoria Sabatino, known for its delicious pastries.
Afternoon
Visit the charming Piazza della Signoria and its surrounding attractions, such as the Palazzo Vecchio. For lunch, try the famous Florentine steak at Trattoria da Mario.
Evening
End your trip with a memorable dinner at La Bussola, a restaurant known for its seafood specialties, followed by gelato at Gelateria Carapina, a popular gelateria in Florence.
Bedtime
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Basilica di Santa Croce

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Piazza della Signoria

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