• Explore San Gimignano, one of Tuscany’s most iconic medieval towns
• Discover the Chianti Classico region, known for its landscapes and wine traditions
• Enjoy wine tastings at local wineries, often family-owned and authentic
• Experience the Tuscan countryside, with rolling hills, vineyards, and scenic roads
• Travel in comfort with a private driver, with a flexible itinerary tailored to your pace

We offer a private Mercedes Minivan and an English-speaking driver who can provide transportation, but we highly recommend adding a private guide for a more memorable experience. A private guide is available for a two-hour tour of San Gimignano. Your driver will be waiting in your hotel lobby or at a convenient meeting point, holding a sign with your name.

Leave the city behind and enter the rolling landscapes of Tuscany, where vineyards, olive groves, and cypress-lined hills unfold in every direction, creating the scenery that defines this region.

Your day unfolds in San Gimignano, a hilltop town unlike any other, where medieval towers rise above the countryside and create one of the most recognizable skylines in Italy.

As you walk through its narrow stone streets, you will move between small squares, artisan shops, and lively corners where everyday life blends naturally with history. The town feels both vibrant and timeless — with local boutiques, small wine bars, and the occasional scent of fresh products and gelato filling the air.

Step into its open piazzas, look up at the towers that once symbolized wealth and power, and take in the views that stretch far beyond the town walls into the surrounding countryside.

With a private guide, the experience becomes richer and more engaging, bringing forward the stories, rivalries, and character that shaped San Gimignano over the centuries.

From here, the journey continues into the heart of Chianti, where the pace naturally slows and the landscape becomes the experience itself.

The road winds gently through vineyards and olive groves, passing historic estates, stone farmhouses, and quiet villages that appear almost untouched by time. This is the rhythm of rural Tuscany — unhurried, authentic, and deeply connected to the land.

In this setting, you may stop at a local winery, often family-owned and set in a peaceful countryside location.

Wine tasting here is relaxed and genuine — not formal, not rushed — where each glass reflects the land, the season, and the work behind it. Conversations flow easily, and the experience feels personal and unfiltered.

You will also have time to enjoy a traditional Tuscan lunch (optional), set in a serene countryside setting where simple dishes, local ingredients, and regional wines come together naturally.

A table, a view, a glass of wine — and nowhere to rush.

Throughout the day, your itinerary remains flexible, allowing you to follow your own rhythm — whether that means spending more time exploring San Gimignano, lingering in the countryside, or simply enjoying the drive.

Because Tuscany is not something to rush.
It is something to experience slowly.

At the end of your experience, relax on the drive back, as the landscape gradually softens behind you — leaving you with the feeling of having truly lived a day in Tuscany.

Elevate your day with a private guide by Mondo Guide.

Your dedicated expert guide will accompany you throughout the journey, sharing engaging storytelling, cultural insight, and authentic local perspective — revealing the true character of each destination.

For groups of 1–8 guests traveling by car or minivan, you may choose a 2-hour private tour of San Gimignano for a more comprehensive experience.

With a private guide, your tour becomes more than a visit — it becomes a personalized and enriching experience designed around you.

For groups of 9–24 guests, multiple minivans will be arranged to ensure maximum comfort and seamless access to both the port and the destinations.

• We recommend sunscreen, sunglasses, and light, comfortable clothing, especially during warmer months
• Comfortable walking shoes are recommended, as visits include walking in historic towns and countryside settings
• Wine tastings and lunch are not included and are paid directly on site
• Please inform us of any dietary restrictions in advance
• This is a private and fully customizable experience, tailored to your preferences