15-day Self-Drive Tour – Tuscan Vineyards
For lovers of Tuscan wines and authentic flavors, this self-drive tour offers the perfect blend of culture, nature, and culinary discoveries. You will travel through the heart of Tuscany, visiting beautiful cities such as Pisa, with its famous Leaning Tower, Florence, the birthplace of art and architecture, and Siena, with its medieval charm and lively, welcoming atmosphere. The journey concludes with a relaxing stay along the Tuscan coast, where you can enjoy the sun, sea, and peace. Along the way, you'll experience the rich Tuscan wine culture at local wineries and savor the regional flavors. This is a unique journey through picturesque towns, rolling landscapes filled with vineyards, and gastronomic delights – perfect for foodies and those seeking the true essence of Tuscany.
Highlights of this Tour
✓ The charming town of Lucca with its historic charm.
✓ Pisa, known for its Leaning Tower.
✓ The historic center of Florence, with the Duomo and Uffizi Gallery.
✓ The medieval city walls of Siena and Piazza del Campo.
✓ The Chianti region and its rolling hills.
✓ The town of San Gimignano, famous for its towers.
✓ The city of Massa Marittima, with its medieval charm.
✓ The beaches of the Tuscan coast, near Castiglione della Pescaia.
15-day Self-Drive Tour – Tuscan Vineyards
☀️ Day 1 - 4 incl.
Agriturismo 168 Luxury Wine Estate near Pisa
Start your journey at this beautiful agriturismo, located amidst 30 hectares of vineyards. The accommodation offers comfortable apartments and charming cottages. Enjoy activities such as mountain biking, fishing, wine tasting, and vineyard tours. For relaxation, you can unwind by the pool, in the sauna, or take part in yoga or cooking classes. Breakfast can be served in your apartment or on the shared terrace. Ideally located for exploring the Tuscan countryside and cities like Lucca and Pisa.
➤ Read more about agriturismo 168 here.
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Appartments
The agriturismo has 10 apartments, spread across the villa and two separate cottages. The apartments are comfortably and stylishly furnished, with amenities like air conditioning, satellite TV, and a DVD player. Some apartments are equipped with a dishwasher.
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What to see and do
The agriturismo is in a region ideal for both hikers and cycling enthusiasts. The area offers a variety of routes, from easy to more challenging trails, with panoramic views of the Tuscan landscape. Pisa and Lucca are just a short drive away. Pisa is famous for its Leaning Tower, but the city has much more to offer, including the Piazza dei Miracoli and its charming streets. Lucca is known for its well-preserved city walls and picturesque Piazza dell'Anfiteatro, built on the ruins of a Roman amphitheater.
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☀️ Day 4 - 8 incl.
Agriturismo 67 Welcoming Wine Estate near Florence
This charming agriturismo, located in the Tuscan hills surrounding Florence, offers a peaceful setting amid vineyards with stunning views. The former winery has been carefully converted into welcoming vacation homes, preserving traditional Tuscan charm. You can enjoy the pool, the shared barbecue area, and participate in wine tasting activities.
➤ Read more about agriturismo 67 here.
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Appartments
The agriturismo has eight apartments, each maintaining authentic Tuscan style with warm colors and natural materials. Each apartment has its own terrace or patio with a table and chairs. At the pool, each apartment has its own spot with loungers and an umbrella. The apartments are equipped with air conditioning, a TV, a kitchen with a 4-burner gas stove, a microwave, and some have a dishwasher and an oven.
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What to see and do
The agriturismo is just 15 kilometers from Florence, a city famous for its rich history and culture. In the historic center, you can visit the famous Duomo, Ponte Vecchio, and the Uffizi Gallery, recognized worldwide as one of the most beautiful museums. From the agriturismo, you can also visit Arezzo, a city known for its medieval charm and antique markets – perfect for those wanting to explore Tuscany beyond the big tourist crowds.
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☀️ Day 8 - 12 incl.
Agriturismo 41 Authentic Wine Estate in Chianti
Located in the beautiful Chianti region, just 10 kilometers from historic Siena, this authentic agriturismo offers the perfect mix of tranquility, nature, and Italian tradition. Surrounded by olive trees and vineyards, it offers stunning views of the Tuscan landscape. Siena, with its rich history and charming streets, is just a 20-minute drive away.
➤ Read more about agriturismo 41 here.
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Suites and rooms
The agriturismo has rustic Tuscan-style suites and rooms, located in a house near the pool and reception. Some rooms and suites have their own terrace, and some suites include a kitchenette. Breakfast is included.
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What to see and do
The agriturismo is perfectly located to explore the region. Siena is a must-visit, with its famous Piazza del Campo, impressive Duomo, and charming streets. Other cities such as San Gimignano, Volterra, and Montepulciano are easily accessible. For those wishing to dive deeper into Tuscan culture and gastronomy, the agriturismo offers wine tastings and meals prepared with local, organic ingredients.
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☀️ Day 12 - 15 incl.
Agriturismo 21 Peaceful Wine Estate near the Coast
This agriturismo is the perfect end to your Tuscan journey. Located in the quiet Maremma region, in southern Tuscany, this authentic farm offers a peaceful environment far from the crowds. After a thorough renovation of the original farmhouse, the owners opened their doors to guests, welcoming you with typical Tuscan hospitality.
➤ Lees hier meer over agriturismo 21.
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Appartments
The agriturismo has 10 cozy apartments, each with a well-equipped kitchen. Ground-floor apartments have their own terrace, while upper-floor apartments have shared seating areas in the garden. You can enjoy the large pool in the beautifully landscaped garden and use the shared barbecue area. Twice a week, a local dinner is served at the restaurant, and wine tastings are available upon request.
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What to see and do
The agriturismo offers a calm setting to relax, but it is also a great base to explore the region. The towns of Massa Marittima and Castiglione della Pescaia are nearby, and the beach is just 40 minutes away – perfect for a relaxing day by the sea.
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Travel Information
With My Italy’s self-drive tours, you explore Italy at your own pace, with your own car. If you'd rather fly and rent a car on site, that’s perfectly fine too! You arrange your own flight and rental car, so you have full freedom. We provide charming agriturismos where you can relax and that serve as the perfect base for unforgettable day trips.
Pricing
Starting price per person for 14 nights, self-catering (breakfast not included).
The price shown is the starting price per person for 14 nights, based on a stay in a double apartment (self-catering). Flights and car rental are not included. My Italy will send you a tailored proposal with the final price, depending on your travel dates and the apartment type you choose.
How to book your road trip:
1. Fill out the inquiry form with your desired start date.
2. We check availability and send you a proposal with the price.
3. If availability is an issue, we offer a suitable alternative.
4. Want to book? You'll receive the booking form.
5.Once completed, you’ll get a confirmation voucher.
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Would you like to stay for less or more than 15 days? Please mention this in the “questions or requests” section of the inquiry form.
