Tuscan Delights: 7-Day Siena and Surroundings Adventure Itinerary

Enjoy a delightful breakfast at Bar Il Palio, known for its morning ambiance. Today's adventure takes you to the picturesque Chianti region. Start with a visit to the Abbey of Sant'Antimo (Abbazia di Sant'Antimo), a serene and ancient abbey surrounded by vineyards.

For lunch, experience the rustic charm of 53100 Street Food & Wine, offering a variety of local delicacies. Post-lunch, embark on the Total Immersion Wine Tour in Chianti, where you'll visit renowned wineries, taste exquisite wines, and enjoy the idyllic Tuscan countryside.

Return to Siena and dine at SaporDivino Restaurant, where you can relish a menu inspired by the day's wine adventures. Cap off the evening with a visit to the Piccolomini Library (Libreria Piccolomini) within the Siena Cathedral, known for its exquisite frescoes.

Start with a breakfast at Archivio del Gusto, a place known for its artisanal pastries. Then, set out to the medieval hill town of San Gimignano. Explore its well-preserved architecture and visit the San Gimignano Cathedral Entry Ticket and the San Gimignano Torre Grossa and Duomo Tickets for panoramic views.

Enjoy a traditional Tuscan lunch at Osteria da Divo, housed in a former 14th-century palace. Afterward, take a leisurely stroll through the town, visiting local artisan shops and savoring the famous gelato.

Return to Siena and dine at La Taverna di San Giuseppe, a cozy restaurant offering a menu of Tuscan specialties. Conclude the day with a relaxing evening walk around the Basilica of San Domenico (Basilica di San Domenico) and the nearby Fonte Gaia (Gaia Fountain).

Enjoy a breakfast at Vineria Tirabusciò Siena, a charming spot with a variety of morning treats. Today, you'll visit the historic town of Montalcino. Explore its winding streets and visit the Montalcino Fortress (Fortezza di Montalcino) for panoramic views of the surrounding countryside.

Have a delightful lunch at Il Bargello, known for its Tuscan cuisine. Afterward, indulge in a Montalcino Brunello Wine Tasting Experience at a local enoteca, savoring the world-renowned wines of the region.

Return to Siena and dine at Enoteca I Terzi, a restaurant celebrated for its wine selection and delectable dishes. After dinner, take a serene walk to the University of Siena and enjoy the peaceful atmosphere of the historic institution.

Start with breakfast at PARTICOLARE di Siena, a place known for its morning offerings. Then, head to the nearby medieval walled town of Monteriggioni. Explore the well-preserved fortifications and enjoy the panoramic views from the town's walls.

For lunch, visit i Parolai Tapas Bar for a unique culinary experience. Post-lunch, participate in a From Siena Chianti Farm Cooking Class, where you'll learn to prepare traditional Tuscan dishes using fresh, local ingredients.

Dine at La Prosciutteria Crudi e Bollicine Siena, a restaurant specializing in cured meats and sparkling wines. After dinner, take a self-guided stroll through the Piazza del Mercato and the charming streets of the Contrada della Torre, one of Siena's historic neighborhoods.

Enjoy a leisurely breakfast at Casato Ristorante Wine Bar, known for its morning ambiance. Spend the morning exploring the lesser-known sites of Siena, such as the Siena Highlights Self-Guided Scavenger Hunt and City Tour, which will take you to hidden gems and provide a unique perspective on the city.

For lunch, visit Old Wild West for a change of pace with some American-style cuisine. Afterward, take a guided walking tour with a local expert, experiencing the city's history and culture from a different angle with the Siena Private Custom Tour with a Local Guide.

Dine at Osteria Enoteca Sotto Le Fonti, a restaurant located in a historic building, offering a refined menu and an extensive wine list. After dinner, enjoy a relaxed evening at the Siena Jazz Foundation, listening to live music in an intimate setting.

Enjoy your final breakfast in Siena at La Prosciutteria Crudi e Bollicine Siena, savoring the flavors of the region. Spend the morning visiting any of your favorite spots in Siena for a last look, or take a moment of quiet reflection at the Baptistery of San Giovanni (Battistero di San Giovanni).

For a memorable farewell lunch, head to Enoteca I Terzi, where you can enjoy the best of Tuscan cuisine and bid adieu to the city. After lunch, take some time to pack and prepare for your departure, or if time allows, take a short trip to the nearby {adjacentCities[1]}, Florence, for a brief exploration.

As the sun sets on your Tuscan adventure, reminisce over a delightful dinner at SaporDivino Restaurant, sharing your favorite moments and experiences. Conclude your evening with a walk to the Porta Camollia, one of the ancient gates of Siena, and take in the views of the city one last time.