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Five Days of Adventure in the Stunning Nature of Tuscany

Viewed by 115 travelers

Day 1: Cortona Exploration

Cortona, Italy on April 12, 2025

8:00AM

Breakfast at Caffè Signorelli

Start your day at this cozy café known for its artisanal pastries and locally sourced coffee. Don't miss their ricciarelli biscuits.
EUR10, 1 hour

9:30AM

Explore Cortona

Wander through the charming medieval streets of Cortona and visit the Diocesan Museum for a taste of local art and history.
EUR8, 2 hours

12:00PM

Lunch at Osteria del Teatro

Savour authentic Tuscan pasta dishes in a rustic setting. Their pici cacio e pepe is a must-try!
EUR20, 1 hour

1:30PM

Hiking in the Val di Chiana

Take a guided hike through the beautiful Val di Chiana landscape, famous for its rolling hills and stunning views.
EUR25, 3.5 hours

5:00PM

Wine Tasting at Avignonesi

Experience a delightful wine tasting at this renowned vineyard, known for its sustainable practices and excellent Vino Nobile di Montepulciano.
EUR30, 2 hours

7:30PM

Dinner at La Bucaccia

Enjoy traditional Tuscan dishes in a warm and welcoming atmosphere. Their wild boar stew will leave you with lasting memories.
EUR30, 1.5 hours
Find Hotels in Cortona

Day 2: Val d'Orcia Day

Val d'Orcia, Italy on April 13, 2025

8:00AM

Breakfast at Pasticceria Corsini

Indulge in delicious pastries and fresh coffee in this local pasticceria before heading out to explore.
EUR8, 1 hour

9:00AM

Visit Pienza

Head to the UNESCO World Heritage site of Pienza, known for its beautiful Renaissance architecture and pecorino cheese.
EUR5, 2 hours

12:00PM

Lunch at La Porta

This charming restaurant has breathtaking views and offers delicious dishes that incorporate local ingredients.
EUR25, 1 hour

1:30PM

Explore Bagno Vignoni

Enjoy the unique thermal waters of Bagno Vignoni, where you can relax and unwind in the ancient pools.
EUR15, 2 hours

4:00PM

Hike the Crete Senesi

Take in the stunning lunar-like landscape of Crete Senesi, perfect for trekking and photography.
Free, 2.5 hours

7:00PM

Dinner at La Cisterna

Savour hearty Tuscan cuisine at this rustic eatery, known for its rich ribollita and fine local wines.
EUR30, 1.5 hours
Find Hotels in Val d'Orcia

Day 3: Montepulciano Wonders

Montepulciano, Italy on April 14, 2025

8:00AM

Breakfast at Caffe Poliziano

Enjoy a delightful breakfast with local pastries and great coffee before exploring the town.
EUR10, 1 hour

9:00AM

Visit Montepulciano

Spend the morning exploring the charming streets of this hilltop town, known for its stunning views and wine.
Free, 2 hours

12:00PM

Lunch at Osteria Acquacheta

Renowned for their hand-rolled pici and delicious wines, this is a must-visit for lunch.
EUR25, 1 hour

1:30PM

Explore the Vino Nobile Wine Cellars

Visit the renowned wine cellars in Montepulciano to learn about their wine production and enjoy tastings.
EUR20, 2.5 hours

4:00PM

Biking in the Countryside

Rent bikes and explore the scenic countryside around Montepulciano, featuring beautiful vineyards and olive groves.
EUR15, 2 hours

6:30PM

Dinner at Ristorante La Grotta

This restaurant offers spectacular views of the rolling hills and a menu filled with delicious Tuscan dishes.
EUR35, 1.5 hours
Find Hotels in Montepulciano

Day 4: Chianti Region Adventure

Chianti, Italy on April 15, 2025

8:00AM

Breakfast at Bar Montalcino

Start your day with fresh local pastries and delicious espresso in Bar Montalcino, a local favourite.
EUR8, 1 hour

9:00AM

Wine Tour in Chianti

Experience an immersive wine tour through the vineyards of Chianti, learning about the winemaking process.
EUR40, 4 hours

1:00PM

Lunch at Osteria del Chianti

Enjoy a traditional Tuscan lunch with panoramic views over the rolling vineyards.
EUR25, 1.5 hours

2:30PM

Visit the Castello di Brolio

Explore the historic castle and grounds, known for its extraordinary history and stunning vistas.
EUR10, 2 hours

5:00PM

Truffle Hunting Experience

Join a delightful truffle hunting tour, led by experts and their trained dogs, in the heart of Chianti.
EUR70, 2 hours

7:30PM

Dinner at Ristorante Il Celliere

Relish Tuscan dishes paired with local wines at this rustic eatery, perfect for a post-adventure meal.
EUR30, 1.5 hours
Find Hotels in Chianti

Day 5: Fiesole Escape

Fiesole, Italy on April 16, 2025

8:00AM

Breakfast at Ristorante La Reggia

Enjoy a delightful breakfast with breathtaking views of Florence at this charming restaurant.
EUR10, 1 hour

9:00AM

Explore Fiesole's Archaeological Sites

Visit the ancient ruins and stunning amphitheatre in Fiesole, offering a fascinating glimpse into Tuscany's past.
EUR10, 2 hours

12:00PM

Lunch at Terrazza del Chianti

Feast on delectable Tuscan delights with views of Florence as a backdrop at this popular terrace restaurant.
EUR25, 1.5 hours

1:30PM

Hike to Monte Ceceri

Take a scenic hike on Monte Ceceri, known for its beautiful walking trails and sweeping views of the surrounding area.
Free, 2.5 hours

4:00PM

Relax at Villa Medici

Stroll through the lovely gardens of Villa Medici and enjoy the tranquil atmosphere.
EUR5, 1 hour

6:00PM

Farewell Dinner at La Sosta dei Barbarini

End your trip with a superb dinner featuring seasonally inspired dishes and excellent wines.
EUR40, 2 hours
Find Hotels in Fiesole
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