Enchanting Siena: A 7-Day Cultural and Culinary Journey in Tuscany

Day 1: Historic Core

Siena, Italy on August 30, 2025

9:00am

Breakfast at La Taverna di San Giuseppe

Start your day with traditional Tuscan breakfast offerings in a charming, rustic setting known for freshly brewed coffee and pastries.
EUR10, 1h0m

10:30am

Visit Piazza del Campo

Explore the famous shell-shaped square at the heart of Siena, renowned for the Palio horse race and surrounding medieval architecture.
Free, 1h0m

11:45am

Tour Siena Cathedral (Duomo di Siena)

Discover the stunning Romanesque-Gothic cathedral famous for its intricate marble floors and beautiful frescoes. Check opening hours: 10:30am - 7:00pm.
EUR15, 1h30m

1:15pm

Lunch at Osteria Le Logge

Enjoy authentic Tuscan cuisine with locally sourced ingredients in a cozy, historic atmosphere close to the cathedral.
EUR30, 1h15m

3:00pm

Explore Museo Civico di Siena

Visit this museum to admire medieval art and artifacts related to Siena’s rich history, housed in the Palazzo Pubblico. Open 10:00am - 7:00pm.
EUR12, 1h30m

5:00pm

Leisurely Walk Along Via di Città and Via Banchi di Sopra

Discover charming shops, cafés, and local boutiques while soaking up everyday Siena life along these iconic streets.
Free, 1h0m

7:30pm

Dinner at Antica Trattoria Papei

Dine on traditional Sienese dishes such as pici pasta and robust Tuscan wines in a friendly and historic setting.
EUR35, 1h30m
View Hotels

Day 2: Art & Views

Siena, Italy on August 31, 2025

8:30am

Breakfast at Nannini Caffè

Indulge in espresso and Italian pastries from one of Siena's beloved cafes, specialising in quality coffee blends.
EUR8, 1h0m

9:30am

Climb Torre del Mangia

Ascend this iconic tower on Piazza del Campo for sweeping panoramic views of Siena and the Tuscan countryside. Open 10:00am - 7:00pm.
EUR10, 1h0m

11:00am

Visit Pinacoteca Nazionale di Siena

Explore Siena’s national gallery, home to a masterful collection of Sienese Renaissance artworks. Open 10:00am - 7:00pm.
EUR12, 1h30m

1:00pm

Lunch at La Prosciutteria Siena

Sample delicious Tuscan cured meats and cheeses served in generous platters in a relaxed and lively space.
EUR20, 1h0m

2:30pm

Walk in Orto de’ Pecci

Relax in this peaceful public garden offering views over the city walls and Mediterranean flora, ideal for a refreshing afternoon pause.
Free, 1h0m

4:00pm

Visit Basilica di San Domenico

Explore this gothic church notable for its frescoes and relics of Saint Catherine of Siena. Open 9:00am - 7:00pm.
Free, 1h0m

6:30pm

Aperitivo at Enoteca Italiana

Enjoy a glass of local wine and light snacks in this renowned wine bar housed in Fortezza Medicea, Siena’s fortress.
EUR15, 1h0m

8:00pm

Dinner at Ristorante Da Enzo

Feast on refined Tuscan dishes with an emphasis on seasonal ingredients in a charming intimate setting.
EUR40, 1h30m
View Hotels

Day 3: Tuscan Countryside

Siena, Italy on September 1, 2025

7:30am

Early Breakfast at Your Accommodation

Enjoy a light breakfast with fresh bread, cheese, and local fruit before your day trip.
Varies, 0h45m

8:30am

Day Trip to San Gimignano

Travel 45 minutes from Siena to this medieval hill town famous for its towers, views and Vernaccia wine. Explore picturesque streets and artisan shops.
EUR20 (bus/train), 6h0m

1:00pm

Lunch at Cum Quibus, San Gimignano

Enjoy a Michelin-starred meal offering creative interpretations of Tuscan dishes in an elegant atmosphere.
EUR50, 1h30m

3:30pm

Visit Torre Grossa & Museo Civico

Climb the tallest tower for views over San Gimignano and visit the civic museum with medieval and Renaissance art.
EUR10, 1h30m

5:30pm

Return to Siena

Relax on the return journey and prepare for a quiet evening.
Included, 1h0m

7:00pm

Dinner at La Chiacchera

Savour authentic Tuscan home cooking in a rustic trattoria, perfect after a full day of sightseeing.
EUR30, 1h30m
View Hotels

Day 4: Wine & Cooking

Siena, Italy on September 2, 2025

8:00am

Breakfast at Bar Pasticceria Nannini

Sample fresh pastries and excellent espresso to start your day in a lively café.
EUR8, 0h45m

9:30am

Half-Day Cooking Class in Siena

Learn to prepare classic Tuscan dishes using fresh, local ingredients with a hands-on chef-led workshop lasting approx. 4 hours.
EUR80, 4h0m

1:30pm

Enjoy the Meal You've Prepared

Sit down to enjoy the delicious food you've cooked, paired with local wines.
Included in cooking class, 1h30m

3:30pm

Relax at your hotel or explore local markets

Take a restful afternoon or wander through the daily Mercato di Piazza Matteotti for fresh produce and artisan products.
Free, 1h30m

6:00pm

Sunset Walk to Fortezza Medicea

Enjoy views across Siena from this 16th-century fortress and its surrounding parklands. The fortress hosts various events and sometimes wine tastings.
Free, 1h0m

8:00pm

Dinner at Osteria Le Logge

Experience a refined dinner featuring Tuscan specialities and excellent service in a central location.
EUR40, 1h30m
View Hotels

Day 5: Historic Estates

Siena, Italy on September 3, 2025

8:00am

Breakfast at Pasticceria Valentini

Enjoy classic Italian bakery treats and coffee in a family-run shop close to Piazza del Campo.
EUR7, 0h45m

9:00am

Day Trip to Chianti Wine Region

Spend the day visiting renowned wineries in the Chianti Classico area, sampling wine and olive oil while enjoying stunning landscapes about an hour’s drive from Siena.
EUR60 tour, 7h0m

12:30pm

Lunch at a Chianti Winery

Relish regional dishes paired with the estate’s own wines in a picturesque vineyard setting.
Included in tour, 1h30m

5:00pm

Return to Siena

Return to your accommodation for a restful evening.
Included, 1h0m

7:30pm

Dinner at Trattoria La Torre

End your day with traditional Tuscan fare in an intimate medieval setting near the city centre.
EUR35, 1h30m
View Hotels

Day 6: Museums & Gardens

Siena, Italy on September 4, 2025

8:30am

Breakfast at Caffè Paszkowski

Enjoy a luxurious breakfast in this elegant historic café in Piazza del Campo.
EUR12, 1h0m

9:30am

Visit Santa Maria della Scala

Explore this former hospital turned museum complex with archaeological sites, frescoes, and contemporary exhibitions. Open 10:00am - 7:00pm.
EUR12, 2h0m

12:00pm

Visit Orto Botanico dell'Università di Siena

Discover Sicily’s oldest botanic garden featuring diverse plants from Tuscany and worldwide, a short walk from the city centre.
EUR5, 1h0m

1:30pm

Lunch at Antica Osteria da Divo

Dine inside ancient Etruscan caves in one of Siena’s highest-rated restaurants offering innovative Tuscan cuisine.
EUR50, 1h30m

3:30pm

Afternoon Stroll in Giardino della Lizza

Relax in these peaceful public gardens offering views over the city walls and shaded walking paths.
Free, 1h0m

5:00pm

Shopping and Coffee Break on Via di Città

Enjoy a leisurely final afternoon browsing local shops and sitting down for an Italian coffee or gelato.
EUR10, 1h0m

7:30pm

Farewell Dinner at La Taverna di San Giuseppe

Celebrate your Siena visit with rich, traditional dishes and excellent wine in the warm atmosphere of this beloved trattoria.
EUR40, 1h30m
View Hotels

Day 7: Departure Day

Siena, Italy on September 5, 2025

8:00am

Light Breakfast at Your Accommodation

Enjoy a simple breakfast before your check-out or departure.
Included, 0h30m

9:00am

Last Walk Around Piazza del Campo

Take a final stroll through Siena’s iconic square to enjoy the morning calm and capture last photographs.
Free, 0h30m
View Hotels