New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Free AI trip planner

5 Days of Luxury in Tuscany

5 Days of Luxury in Tuscany Itinerary

Last updated: 2024 Jun 29

Welcome to Tuscany and Wine Tasting Extravaganza

Morning
Start your luxurious journey in Tuscany with a visit to the charming town of Montalcino. Begin your day by exploring Montalcino, a picturesque hilltop town known for its stunning views and rich history. Wander through its narrow streets, visit local shops, and soak in the authentic Tuscan atmosphere.
Afternoon
In the afternoon, head to the impressive Montalcino Fortress (Fortezza di Montalcino). This historic fortress offers panoramic views of the surrounding vineyards and countryside. Explore its ancient walls and imagine the battles that once took place here. Afterward, enjoy a leisurely lunch at Osteria di Porta al Cassero, known for its delectable Tuscan cuisine.
Evening
For an unforgettable evening experience, indulge in VIP Private Montalcino Wine Tasting in Paradiso with Dinner. This exclusive tour will take you to one of Montalcino's finest wineries, where you'll savor exquisite Brunello wines paired with a gourmet dinner. The combination of fine wine, delicious food, and breathtaking scenery will set the perfect tone for your luxurious trip.
Bedtime
Find amazing hotels in Tuscany.

Historical Sites and Gourmet Delights

Morning
Begin your second day with a visit to the serene Abbey of Sant'Antimo (Abbazia di Sant'Antimo). This beautiful Romanesque abbey is nestled in the Val d'Orcia countryside and offers a peaceful retreat from the hustle and bustle. Take a moment to appreciate its stunning architecture and tranquil surroundings.
Afternoon
After exploring the abbey, embark on an exciting adventure with Val d'Orcia: Horse Trekking Trip and Picnic under the Oak. This unique tour allows you to experience Tuscany's natural beauty on horseback while enjoying a delightful picnic under an ancient oak tree. It's a perfect way to connect with nature and unwind.
Evening
As evening falls, treat yourself to an exquisite dining experience at Ristorante Il Leccio in nearby Sant'Angelo in Colle. Known for its elegant ambiance and gourmet dishes, this restaurant offers a true taste of Tuscan cuisine. Savor each bite as you reflect on your day's adventures.
Bedtime
Find amazing hotels in Tuscany.

Scenic Tours and Culinary Experiences

Morning
Start your third day with an invigorating activity by joining Pienza: Scenic hiking on the Gladiator's movie location. This guided hike takes you through some of Tuscany's most iconic landscapes featured in famous films like Gladiator. Enjoy breathtaking views as you explore these cinematic locations.
Afternoon
After your hike, head over to Pienza for lunch at La Terrazza del Chiostro, which offers stunning views over Val d'Orcia along with delicious regional dishes made from fresh local ingredients.
Evening
In the evening, immerse yourself in Tuscan culinary traditions by participating in Cooking Class in a Brunello Winery - Private experience. Learn how to prepare traditional Tuscan dishes using locally sourced ingredients while sipping on world-renowned Brunello wines produced right at this winery.
Bedtime
Find amazing hotels in Tuscany.

Truffle Hunting and Wine Adventures

Morning
Kick off your fourth day with an extraordinary experience by joining Trequanda: Tuscan Truffle Hunting Experience with Lunch. This unique tour will take you through the beautiful forests of Trequanda, where you'll hunt for prized truffles guided by an expert truffle hunter and their trained dogs. After the hunt, enjoy a sumptuous lunch featuring the truffles you've found, paired with local wines.
Afternoon
In the afternoon, continue your culinary journey with a visit to Montepulciano: Winery and Perfume Laboratory Sensory Tour. This exclusive tour combines wine tasting with a sensory experience in a perfume laboratory. Discover how scents and flavors intertwine as you sample exquisite wines and create your own personalized fragrance.
Evening
For dinner, head to Osteria Acquacheta in Montepulciano. Known for its rustic charm and delicious steaks cooked over an open flame, this restaurant offers an authentic taste of Tuscan cuisine. Savor each bite as you reflect on your day's adventures.
Bedtime
Find amazing hotels in Tuscany.

E-Bike Exploration and Farewell Dinner

Morning
Pienza: Guided E-bike Tour through the Val d'Orcia is the perfect way to start your final day in Tuscany. This guided e-bike tour takes you through the stunning landscapes of Val d'Orcia, allowing you to cover more ground while enjoying the fresh air and breathtaking views. Stop at various points of interest along the way to capture memorable photos.
Afternoon
After your e-bike adventure, treat yourself to a relaxing afternoon at Caffè La Posta in Pienza. Enjoy a leisurely lunch featuring local specialties while soaking in the charming atmosphere of this historic town.
Evening
Val d'Orcia: Magical 3-Course Dinner under the Oak Tree is the perfect way to conclude your luxurious trip to Tuscany. This enchanting dining experience takes place under a centuries-old oak tree in Val d'Orcia. Savor a delectable three-course meal prepared with fresh local ingredients as you dine al fresco surrounded by nature's beauty.
Bedtime
Find amazing hotels in Tuscany.

Top Tuscany Travel Videos

Adjacent Cities

kayakFind the right stay during your trip.
Got a question about your trip?