Tuscan Escape: Siena, San Gimignano & Chianti Countryside Itinerary

Embark on a self-guided exploration of the picturesque town, visiting iconic sites such as the San Gimignano Tower (Torre Grossa) and the San Gimignano Cathedral (Duomo). Enjoy a delightful breakfast with a view at La Taverna di San Giuseppe, known for its panoramic terrace.

Participate in a San Gimignano Cheese and Wine Tasting Tour, where you'll sample the renowned Vernaccia wine and local cheeses. Later, take a leisurely drive to the Castle of Meleto (Castello di Meleto), exploring the historic grounds and vineyards. For lunch, enjoy a picnic with provisions from the castle's own kitchen.

Return to San Gimignano and spend a relaxed evening exploring the town's artisan shops and galleries. Dine at Osteria Le Logge, where the menu is a blend of traditional and innovative dishes, reflecting the rich history and culture of Tuscany.

Begin your day with a visit to the Siena Cathedral (Duomo), using your skip-the-line entry. Explore the magnificent cathedral and the Piccolomini Library at your own pace. Afterward, enjoy a delightful breakfast at La Taverna di San Giuseppe, with its panoramic views of San Gimignano's skyline.

Spend a leisurely afternoon at the Siena Private custom tour with a local guide, allowing you to discover the hidden gems and history of this ancient city. For lunch, indulge in the regional cuisine at Osteria La Porta in Monticchiello, a short drive from Siena.

As the sun begins to set, unwind at the Relax in a Tuscan Villa with Local Wine and Typical Products, where you can enjoy the serene countryside, sipping on local wines and savoring Tuscan appetizers. Conclude the day with a sumptuous dinner at La Bottega del Nobile in Montepulciano, known for its elegant ambiance and refined menu.

Embark on the From Siena Chianti and Castles Tour with Wine Tastings, immersing yourself in the scenic landscapes and visiting well-preserved castles. Enjoy a hearty breakfast at Ristorante Il Falconiere, set in the heart of the Chianti countryside.

Savor the flavors of Tuscany with a visit to Chianti Winery, where you'll indulge in a wine tasting session. Later, enjoy a leisurely lunch at La Grotta di Montepulciano, nestled in the hills of Montepulciano and offering panoramic views.

Take a private custom tour with a local guide, exploring hidden gems and secret spots known only to the residents. Conclude the day with a memorable dinner at Il Canto del Maggio, where the menu is a fusion of Tuscan tradition and contemporary creativity.

Embark on the From Siena Val D'Orcia Wine Tour, visiting vineyards and cellars while taking in the breathtaking views of the Val d'Orcia. Enjoy a delightful breakfast at Trattoria da Burde, known for its rustic Tuscan dishes.

Explore the charming village of Montalcino, famous for its wine. Visit a Brunello di Montalcino Winery and indulge in a tasting session. For lunch, enjoy the warm hospitality and regional cuisine at Trattoria Mario, a favorite among locals and visitors alike.

Relax in the thermal waters of Bagno Vignoni, a unique village with a large thermal pool at its center. Later, enjoy a leisurely dinner at La Bottega del Nobile, where the menu is a celebration of the finest local ingredients and flavors.

Begin your day with a visit to the Pisa Cathedral (Duomo) and the iconic Leaning Tower of Pisa (Torre di Pisa). After marveling at these architectural wonders, enjoy a traditional Pisan breakfast at Enoteca I Terzi, known for its local wines and gastronomic delights.

Explore the Cinque Terre, a stunning coastal area comprised of five picturesque villages. Enjoy the breathtaking views and a delicious seafood lunch at Osteria dell'Orsa, known for its fresh, regional dishes.

Conclude your Tuscan adventure with a visit to the vibrant Mercato dell'Usato di Pisa, a flea market where you can find unique souvenirs and antiques. For your final dinner, indulge in the innovative cuisine of Osteria Acquacheta, known for its creative dishes and welcoming atmosphere.