Poggibonsi

Day Trips

Make the most of your day with our curated plans, packed with Poggibonsi's hidden gems and unique experiences!

day 1
Arrival in Poggibonsi
morning
:

Arrive in Poggibonsi and settle into your accommodation. Take a leisurely stroll around the charming town center, absorbing the rustic ambiance and breathtaking Tuscan landscapes. Enjoy your first Italian breakfast at a local café, indulging in fresh pastries and coffee.

afternoon
:

Visit the impressive Palazzo Comunale, an architectural gem that offers insights into the town's history. Spend time exploring the nearby ruins of the ancient castle, La Fortezza Medicea, and enjoy panoramic views of the surrounding countryside. Stop for a light lunch at a trattoria, trying out local specialties.

evening
:

As the sun sets, find a cozy trattoria to savor authentic Tuscan dishes paired with local wine. Experience the vibrant culture of Poggibonsi through a casual walk among the narrow streets, where you may encounter local artisans. End your day with a gelato from a nearby gelateria while listening to live music in the piazza.

day 2
Exploring San Gimignano
morning
:

Take a short trip to the enchanting medieval town of San Gimignano, known for its well-preserved towers. Explore the cobbled streets and visit the Collegiate Church of Santa Maria Assunta, famous for its stunning frescoes. Don't forget to sample the local Vernaccia wine at a vineyard.

afternoon
:

Spend time exploring the local shops that sell handmade pottery, textiles, and other traditional crafts. Enjoy lunch at a local café, where you can enjoy the serene views of the surrounding vineyards. Consider visiting the San Gimignano 1300 museum to learn about the town's history and evolution.

evening
:

Return to Poggibonsi and unwind with a traditional Italian dinner at a family-owned restaurant. Experience the local hospitality and try out dishes that reflect the region's culinary heritage. Finish the night with a peaceful walk alongside the River Elsa.

day 3
Wine Tasting in Chianti
morning
:

Embark on a wine tour in the beautiful Chianti region, famous for its vineyards and rolling hills. Visit several wineries to learn about the wine-making process and taste a variety of Chianti wines. Enjoy a scenic drive through the picturesque landscapes dotted with olive groves and charming villas.

afternoon
:

After a morning of tasting, indulge in a savory lunch at a winery featuring local dishes paired with wine. Take a leisurely stroll through the vineyards, soaking in the Tuscan sun and tranquil surroundings. Visit the small village of Castellina in Chianti for a little shopping and exploring.

evening
:

Return to Poggibonsi to relax and enjoy dinner at a rooftop restaurant with sweeping views of the Tuscan landscape. Share experiences from the day's adventures over glasses of local wine. Conclude your evening by taking a walk through the illuminated streets of Poggibonsi.

day 4
Cultural Exploration in Florence
morning
:

Take a day trip to Florence, the cradle of the Renaissance, and start your exploration at the iconic Duomo. Marvel at the intricate architecture both outside and within, and consider climbing to the dome for spectacular views. Afterward, visit the Galleria degli Uffizi to admire masterpieces by Botticelli and Michelangelo.

afternoon
:

Enjoy lunch at a bistro in Florence featuring traditional Florentine steak. Spend your afternoon soaking in the local art scene at the Accademia Gallery, home of Michelangelo's David. Wander through the bustling streets of Florence, looking for unique souvenirs and local artisan goods.

evening
:

Head back to Poggibonsi and treat yourself to a quiet dinner at a local osteria. Reflect on your enriching day filled with art and culture while savoring the flavors of homemade pasta. End the evening with a nightcap at a wine bar, reminiscing about your adventures.

day 5
Adventure in Siena
morning
:

Plan a visit to the historical city of Siena, renowned for its medieval architecture and the Palio horse race. Start your day at Piazza del Campo, one of Italy's finest squares, and visit the stunning Siena Cathedral. Explore the narrow streets lined with shops selling local crafts and delicacies.

afternoon
:

Have lunch at a traditional pizzeria in Siena, savoring authentic flavors of the region. Spend the afternoon visiting the Museo dell'Opera del Duomo, which showcases art and treasures from the cathedral. Take your time to admire the intricate details and grandeur of the buildings surrounding the piazza.

evening
:

Return to Poggibonsi and enjoy dinner at a restaurant known for its seasonal dishes. Share a meal with locals to exchange stories and experiences of your travels. Celebrate your time in Tuscany with a final gelato, soaking up the evening ambiance of the town.

day 6
Cooking Class Experience
morning
:

Dedicate your day to a unique cooking class where you will learn to make classic Tuscan dishes from scratch. Start with a tour of the local market, picking the freshest ingredients for your meal. Return to the kitchen to begin crafting your handmade pasta and sauces alongside a professional chef.

afternoon
:

During the cooking class, enjoy the fruits of your labor by sitting down to a leisurely lunch of the dishes you prepared. Share a glass of wine and engage in conversations about Italian cuisine and cooking techniques. Explore a little more of Poggibonsi, focusing on delicatessens or bakeries for local snacks.

evening
:

Celebrate your culinary successes with a casual dinner at a pizzeria, reminiscing about the day's delicious activities. Immerse yourself in the dining experience and try different types of pizza that Italy has to offer. Conclude your day enjoying a nightcap at a local bar, reflecting on your cooking accomplishments.

day 7
Outdoor Exploration and Nature Hike
morning
:

Begin your day with a hike in the stunning Chianti landscape, taking in the natural beauty of vineyards and olive groves. Follow the trails that offer breathtaking views, providing a perfect setting for photography enthusiasts. Pause for breakfast in the woods, enjoying the fresh air and tranquility.

afternoon
:

After your hike, head to a rustic farmhouse for a delightful lunch featuring local produce, cheeses, and meats. Engage with the friendly locals, learning about their way of life and the importance of the land. Spend the rest of your afternoon visiting nearby waterfalls or smaller villages, soaking in nature.

evening
:

Return to Poggibonsi and settle in for a relaxing dinner at a restaurant known for farm-to-table dining. Share stories of your day with fellow travelers or locals, creating bonds over good food. Wrap up your evening with a leisurely stroll around the town, observing daily life in Poggibonsi.

day 8
Relaxation and Spa Day
morning
:

Take a well-deserved break with a day focused on relaxation and rejuvenation at a local spa. Start your day with soothing treatments that incorporate traditional Tuscan ingredients. Enjoy a light breakfast styled like a spa retreat, featuring fresh juices and wholesome foods.

afternoon
:

Spend your afternoon indulging in various spa services tailored to rejuvenate you after days of exploration. Consider a massage or spa bath that utilizes local herbs and oils for a truly authentic experience. Have a healthy lunch at the spa's restaurant, featuring Mediterranean-inspired dishes.

evening
:

After a day of pampering, enjoy a low-key dinner at a nearby eatery that offers a tranquil setting. Reflect on your journey while savoring dishes that highlight local produce and cuisine. End your evening with a peaceful walk, letting the calming effects of the day linger.

day 9
Final Day and Souvenir Shopping
morning
:

Spend your last morning in Poggibonsi enjoying a leisurely breakfast at your favorite café, indulging in one last taste of local pastries. Take a moment to savor the ambiance and reflect on your wonderful experiences during your stay. Visit any remaining sites or favorite spots before departing.

afternoon
:

Dedicate your afternoon to souvenir shopping, exploring artisan shops for handmade crafts, wines, and culinary treasures to take home. Engage with local artisans and learn about their crafts, creating lasting memories. Have a light lunch at a café, soaking in the last rays of Tuscan sunshine.

evening
:

Finish your journey with a heartfelt dinner at a beloved local restaurant, sharing laughter and stories with newfound friends. Take a moment to appreciate the beauty that surrounds you as you enjoy your final meal. Depart Poggibonsi with unforgettable memories and a piece of Tuscany in your heart.

Discover Poggibonsi

Read more in our Poggibonsi 2025 Travel Guide.

Poggibonsi Travel Guide