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Tuscan Road Trip: Chianti, San Gimignano, and Siena Itinerary

Last updated: 2024 Jun 14

Chianti Wine Tasting Delight

Morning

Start your day with a scenic drive through the vineyards of Chianti. Visit the Castle of Meleto (Castello di Meleto) and enjoy a guided tour of the historic castle followed by a wine tasting session.

Afternoon

For lunch, savor traditional Tuscan cuisine at Osteria de' Benci, known for its authentic dishes. Afterward, continue your wine exploration with a visit to the Brolio Castle (Castello di Brolio). Explore the castle and its vineyards, and taste the renowned Chianti Classico wines.

Evening

Conclude the day with a relaxing dinner at Borgo Antico Firenze, a charming restaurant with a cozy atmosphere, offering a mix of local and international flavors.

Bedtime

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Medieval Marvels in San Gimignano

Morning

Drive to the medieval hill town of San Gimignano. Explore the well-preserved San Gimignano, known for its iconic towers and medieval architecture. Climb one of the towers for panoramic views of the surrounding countryside.

Afternoon

Enjoy a leisurely lunch at Il Pizzaiuolo, a popular pizzeria in the heart of San Gimignano. Afterward, visit the Medici Riccardi Palace (Palazzo Medici Riccardi) and admire its Renaissance architecture and art collection.

Evening

Dine at La Ménagère, a unique dining concept that combines a restaurant, flower shop, and home decor store in a stunning setting. Indulge in a mix of traditional and innovative dishes.

Bedtime

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Siena: Art, Culture, and Cuisine

Morning

Head to the historic city of Siena. Visit the Siena Cathedral (Duomo di Siena) and marvel at its Gothic architecture and the stunning mosaics in the Piccolomini Library. Climb the Torre del Mangia for panoramic views of the city.

Afternoon

For lunch, enjoy a meal at Cantinetta Antinori, a renowned restaurant offering a selection of Tuscan dishes and wines. Afterward, explore the Piazza del Campo, the heart of Siena and site of the famous Palio horse race.

Evening

Dine at Enoteca Pinchiorri, a Michelin-starred restaurant known for its exquisite tasting menus and extensive wine list. Experience a culinary journey in a luxurious setting.

Bedtime

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Chianti Countryside and Culinary Delights

Morning

Spend the morning exploring the picturesque villages of Chianti. Visit Greve in Chianti and enjoy the local market and the charming streets. Stop by a winery for a tour and tasting.

Afternoon

Have a traditional Tuscan lunch at Ristorante del Fagioli, a family-run restaurant known for its homestyle cooking. After lunch, visit the Castello di Verrazzano for a wine tour and tasting.

Evening

Enjoy a relaxed dinner at Trattoria Sostanza, a local favorite famous for its butter chicken and Florentine steak. Experience the authentic flavors of Tuscany.

Bedtime

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Art and Architecture in Florence

Morning

Return to Florence and spend the morning exploring the Uffizi Galleries (Gallerie degli Uffizi). Admire masterpieces by Renaissance artists and enjoy the panoramic views of the city from the gallery.

Afternoon

For a late lunch, head to Trattoria Za Za, a popular restaurant near the Florence Central Market (Mercato Centrale). Afterward, visit the Accademia Gallery (Galleria dell'Accademia) to see Michelangelo's iconic David.

Evening

Conclude your trip with a farewell dinner at Cibrèo Trattoria, a renowned restaurant known for its innovative take on traditional Tuscan cuisine. Enjoy a memorable dining experience before departing the next day.

Bedtime

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