About this tour
A private four-hour drive from Siena to Florence through the Chianti countryside, stopping at two medieval hilltop settlements. Your local driver navigates you past vineyards and cypress groves to Monteriggioni, a 13th-century fortress built by Siena's republic, then San Gimignano with its famous tower-studded skyline and artisan workshops. The minivan is comfortable with ample luggage space, and you can arrange a winery or farm lunch en route for an extra fee.
Highlights
- Medieval fortress at Monteriggioni, once a Siena outpost
- San Gimignano's iconic towers and craftsperson-run shops
- Rolling Chianti vineyards and cypress-lined roads
- Private vehicle with knowledgeable local driver
- Optional organic farm lunch or wine tasting stop
- Climate-controlled minivan with spacious boot
What to expect
You'll be collected from your Siena address and travel north through quintessential Tuscan landscape. At Monteriggioni, a short stop lets you wander the compact hilltop village and its fortification walls, built as a medieval garrison on the pilgrimage route south. The second stop is San Gimignano, where you'll have time to explore narrow streets lined with tower houses—genuine medieval architecture, not reconstructed theme-park versions—and galleries and shops run by local craftspeople. The drive itself is the journey; expect winding roads and frequent photo stops. You'll arrive in Florence by late afternoon.
Good to know
Bottled water provided. Infant seats available on request. Suitable for all fitness levels and wheelchair accessible. To add a farmhouse lunch or wine tasting, arrange this with your driver on the day; costs vary by duration and menu. Bring sun protection and comfortable walking shoes for the village stops.
Tour sold and operated by Viator via Viator. Descriptions on this page are original BugBitten summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.