Pisa and Chianti in One Day: Private Tour with Lunch and Wine Tasting
From the Leaning Tower to rolling Tuscan vineyards, all in a single unforgettable day.
This private Pisa and Chianti wine tour takes you from the iconic Piazza dei Miracoli to the heart of the Tuscan countryside, combining two of Tuscany's most celebrated destinations into one well-crafted full-day experience. You travel in comfort with a dedicated driver and vehicle, with no shared groups or fixed crowds to navigate. Every stop is designed to offer genuine access to the region's history, landscape, and culinary culture.
The morning begins in Pisa, where you will have free time to explore one of Italy's most recognizable UNESCO World Heritage Sites at your own pace. The afternoon shifts entirely to the Chianti countryside, where cypress-lined roads, sun-drenched vineyards, and medieval hilltop towns define the scenery.
A traditional three-course Tuscan lunch at a family-run estate forms the centerpiece of the afternoon, complete with guided tastings of regional wines, extra virgin olive oils, and balsamic vinegars. The day concludes with a visit to San Gimignano, a perfectly preserved medieval town known for its distinctive towers and panoramic views over the Sienese hills.
Tour Highlights
Visit the Leaning Tower, Cathedral, Baptistery, and Monumental Cemetery at Pisa's Piazza dei Miracoli, a UNESCO World Heritage Site.
Drive through the Chianti wine region along a scenic route lined with vineyards, cypress avenues, sunflowers, and medieval villages.
Enjoy a traditional three-course Tuscan lunch at a local estate with views of San Gimignano's towers on the horizon.
Take part in a guided tasting of five regional wines, including Chianti, Vernaccia di San Gimignano, and Super Tuscan varieties.
Visit the vineyard and cellar to learn firsthand about the production process behind some of Tuscany's most celebrated wines.
Explore San Gimignano, a UNESCO-listed medieval town famous for its intact towers, historic walls, and far-reaching countryside views.
Travel exclusively as a private group with door-to-door pickup and drop-off at your Florence accommodation.
Itinerary
Your professional driver collects you directly from your hotel, B&B, or any agreed location in Florence. You travel in a comfortable private vehicle throughout the entire day.
The first stop is Pisa, where you will have free time to explore the Piazza dei Miracoli at your own pace. The square contains the Leaning Tower, the Cathedral, the Baptistery, and the Monumental Cemetery, all of which form part of a single UNESCO World Heritage Site.
After Pisa, the route heads into the Chianti wine region, passing through rolling hills, vineyard-covered slopes, and cypress-lined roads. The landscape here represents the most iconic version of the Tuscan countryside.
At a family-run estate near San Gimignano, you will visit the vineyards and cellar before sitting down to a traditional three-course Tuscan lunch. The meal is accompanied by tastings of five wines, five extra virgin olive oils, and three balsamic vinegars, each with explanations of the production process.
The afternoon continues with a transfer to San Gimignano, where you have free time to walk the cobblestone streets, visit the main squares, and take in views of the surrounding Tuscan countryside. The town's medieval towers and intact fortifications make it one of the best-preserved historic centers in Italy.
At the end of the visit, your driver returns you directly to your Florence accommodation, completing a full day across two of Tuscany's most celebrated regions.
What Is Included
Included
- Private professional driver and comfortable vehicle throughout the day
- Door-to-door pickup and drop-off at Florence accommodation
- Visit to Piazza dei Miracoli in Pisa (free time, entrance fees not included)
- Scenic drive through the Chianti wine region
- Guided visit of vineyards and wine cellar at a local estate
- Traditional three-course Tuscan lunch at a family-run farm
- Tasting of 5 regional wines (Chianti, Vernaccia di San Gimignano, Super Tuscan)
- Tasting of 5 extra virgin olive oils
- Tasting of 3 balsamic vinegars with production explanations
- Free time in San Gimignano medieval town
Not Included
- Entrance tickets to Pisa monuments (Leaning Tower, Cathedral, Baptistery)
- Personal expenses and souvenirs
- Gratuities (optional, at your discretion)
- Travel insurance
- Any meals or drinks beyond what is specified in the itinerary
Important Information
Reserve Your Private Tuscany Day Tour
Spaces on this private tour are limited by design. Secure your spot in advance to guarantee availability on your preferred travel date.
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