San Casciano in Val di Pesa

Day Trips

Make the most of your day with our curated plans, packed with San Casciano in Val di Pesa's hidden gems and unique experiences!

day 1
Arrival and Evening Stroll
morning
:

Arrive in San Casciano in Val di Pesa and check into your accommodation. Take some time to unwind and absorb the beautiful Tuscan landscape. Enjoy a leisurely breakfast at a local café, featuring fresh pastries and coffee.

afternoon
:

Explore the picturesque town, visiting its charming shops and historic sites like the Pieve di San Casciano. Stop for lunch at a traditional trattoria, savoring the flavors of Tuscan cuisine. Spend the afternoon wandering the vineyards that surround the town, taking in the stunning views.

evening
:

As the sun sets, find a spot in the main square to enjoy an aperitivo, soaking in the local atmosphere. Delight in a delicious dinner at a renowned restaurant, indulging in homemade pasta and regional wines. Afterward, take a leisurely stroll through the candle-lit streets, appreciating the beauty of the town at night.

day 2
Wine Tasting Experience
morning
:

Start your day with a breakfast featuring local cheeses and fresh bread. Head to a nearby vineyard for a guided wine tour to learn about the winemaking process in this renowned region. Participate in a wine tasting session to sample Chianti wines paired with bites of artisanal snacks.

afternoon
:

Visit a local olive oil producer to explore the world of Tuscan olive oil. Enjoy a tasting to understand the difference between various oils and how they complement local cuisine. Take a late afternoon leisurely bike ride through the countryside, soaking in the intoxicating Tuscan scenery.

evening
:

After freshening up, dine at a local pizzeria where you can try authentic wood-fired pizzas. Engage with locals and fellow travelers to share stories of your Italian adventure. Cap off your evening with gelato from a nearby gelateria, experiencing a classic Italian treat.

day 3
Cultural Immersion in Art
morning
:

Visit a local art gallery showcasing works from regional artists, immersing yourself in the rich cultural history of Tuscany. Participate in an art workshop where you can try your hand at painting or pottery. Enjoy a coffee break at a quaint café, reflecting on your morning activities.

afternoon
:

Explore the local museum to learn more about the history and traditions of San Casciano in Val di Pesa. Join a guided walking tour to discover hidden gems and lesser-known spots in the town. Break for lunch at a family-run osteria, sampling traditional dishes.

evening
:

Experience an interactive cooking class where you can create your own Tuscan meal from scratch. Engage with the chef and fellow participants as you learn the secrets of Italian cooking. Enjoy the fruits of your labor during a communal dinner, mingling over dishes you crafted together.

day 4
Outdoor Adventures
morning
:

Rise early for a guided hike in the surrounding Chianti hills, taking in breathtaking views and the serene landscape. Look out for local wildlife and wildflowers blooming in the countryside. Post-hike, reward yourself with a hearty breakfast featuring local ingredients.

afternoon
:

Spend your afternoon exploring nearby castles and ancient ruins, diving into the region’s rich history. Sample artisanal chocolates and confections at a local chocolatier. Enjoy lunch in a scenic garden restaurant, surrounded by nature.

evening
:

Return to San Casciano for a leisurely evening at a wine bar, sampling local wines. Join a small group for a storytelling session about Tuscan folklore and legends. Wrap up your day with an evening walk along the scenic pathways of the town.

day 5
Exploring Smaller Towns
morning
:

Take a day trip to nearby San Gimignano, known for its medieval towers. Enjoy breakfast in the town square, surrounded by stunning architecture. Visit the local markets to buy handcrafted goods and souvenirs.

afternoon
:

Tour the famous Gelateria Dondoli, awarded for its delicious gelato, before heading to a wine estate to continue your wine tasting journey. Afterward, visit the impressive cathedral in the town center. Enjoy a leisurely lunch at a terrace restaurant with spectacular views.

evening
:

Return to San Casciano to have dinner at an elegant restaurant that highlights local agricultural products. Enjoy live music in the piazza, indulging in the ambiance and energy of an Italian evening. Spend the rest of your night relaxing with a espresso, recounting the day's adventures.

day 6
Farm Stay Experience
morning
:

Transfer to a nearby agriturismo to immerse yourself in authentic Tuscan farm life. Participate in morning farm activities, learning about organic farming practices. Enjoy a hearty farm-fresh breakfast prepared with ingredients sourced from the estate.

afternoon
:

Engage in a seasonal workshop, such as cheese making or gardening, enhancing your understanding of local gastronomy. Walk around the farm, taking photographs and enjoying the beautiful landscape. For lunch, have a rustic meal featuring produce from the land.

evening
:

Participate in a memorable farmhouse dinner, sharing dishes that showcase the flavors of the region. Enjoy homemade desserts prepared by the family. As night falls, gaze at the stars from the comfort of the farm, savoring the tranquility of rural life.

day 7
Relaxation Day
morning
:

Dedicate your morning to relaxation with a visit to a local spa that offers traditional Tuscan treatments. Enjoy a rejuvenating massage or facial, feeling the stress melt away. Reward yourself with a leisurely breakfast of fresh fruit and pastries at the spa.

afternoon
:

Spend the afternoon leisurely exploring the serene countryside, either by foot or bicycle. Find a quiet spot for a picnic lunch, immersing yourself in nature. Consider settling down with a good book, surrounded by olive groves and vineyards.

evening
:

Return to San Casciano to enjoy a light dinner at a vineyard restaurant known for its eco-friendly practices. Take in the scenic views during sunset, sipping on a local wine. After dinner, enjoy an evening of stargazing, reflecting on your relaxing day.

day 8
Gastronomic Tour
morning
:

Begin your day with a visit to a local market to explore fresh produce, cured meats, and artisanal cheeses. Enjoy breakfast featuring local delicacies such as schiacciata and cured meats. Engage with local vendors and learn about their products.

afternoon
:

Join an organized food tour that takes you through some of the finest eateries in the area, sampling a variety of traditional dishes. Experience a behind-the-scenes look at how local specialties like ribollita and pici are made. Take a break to savor a leisurely lunch, indulging in Tuscan specialties.

evening
:

End the culinary adventure with a multi-course meal at one of San Casciano's best restaurants, enjoying carefully paired wines. Experience the communal Italian dining culture, sharing food and stories with fellow food lovers. Conclude the day with an evening walk, absorbing the essence of the town.

day 9
Final Day and Departure
morning
:

Spend your last morning savoring a leisurely breakfast while overlooking the Tuscan hills. Take a final stroll through the town, visiting any last-minute shops or favorite spots one last time. Capture photos of your favorite moments for memories.

afternoon
:

Prepare for departure with a stop at a farm stand for some local products to take home. Enjoy a farewell lunch at a favorite café or restaurant, reflecting on your incredible journey through Tuscany. Make your way back to your accommodation to pack.

evening
:

As your adventure comes to an end, savor a final gelato while reminiscing about your experiences. Depart from San Casciano, carrying the essence of Tuscany in your heart and mind. Look forward to returning someday to this enchanting part of Italy.

Discover San Casciano in Val di Pesa

Read more in our San Casciano in Val di Pesa 2025 Travel Guide.

San Casciano in Val di Pesa Travel Guide