Chianti Wine & San Gimignano Tour with Under The Tuscan Sun Tours - Florence

Chianti Wine & San Gimignano Tour with Under The Tuscan Sun Tours

Florencemoderate

Difficulty

moderate

Duration

6 hours

Fitness Level

Average physical fitness required; some walking and climbing involved

Overview

Join a small group tour from Florence to experience Tuscany’s rich history, savor award-winning Chianti wines, and explore the medieval streets of San Gimignano. Discover why this region is a must-visit for wine lovers and history buffs alike.

Details

In the rolling hills of Tuscany, the town of Florence serves as a starting point for a journey into the region’s rich history, vibrant culture, and world-renowned gastronomy. Under The Tuscan Sun Tours offers a 6-hour shared small group experience that immerses you in the very heart of Tuscany’s iconic landscape. As your group of up to eight travelers departs Florence, the scenery shifts from bustling city streets to scenic vineyards, olive groves, and ancient stone towns. The first highlight is San Gimignano, a UNESCO World Heritage site famous for its medieval skyline studded with soaring towers. Climbing the Great Tower offers sweeping views over the surrounding countryside, while wandering its cobblestone streets reveals centuries of history and local artisanship. Lunch is a highlight, with a regional feast paired with tastings at a premier Chianti winery. Here, you can sample award-winning wines crafted from grapes grown in the AD-18th-century vineyards, complemented by local cheeses and fresh pasta. Afterward, a visit to a nearby vineyard allows you to savor traditional winemaking techniques, making this trip a perfect blend of cultural immersion and culinary delight. This tour is designed to give a genuine taste of Tuscany's storied past and vibrant present, giving visitors a chance to relax, learn, and indulge amidst some of Italy’s most iconic scenery. Whether you're a seasoned wine connoisseur or a curious traveler, the intimate group setting and expert guides make this experience both educational and enjoyable. It’s an ideal day for those looking to see the historic sights, sample remarkable wines, and enjoy the timeless charm of Tuscany in a relaxed, friendly atmosphere.

Adventure Tips

Wear comfortable shoes

Many sites and cobblestone streets require sturdy footwear for navigating uneven surfaces.

Book in advance

Popular tours fill quickly, especially during peak season, so reserve your spot early.

Bring a camera

The views from San Gimignano’s towers and vineyard landscapes are perfect for photos.

Stay hydrated

Tuscany’s summer sun can be intense—drink plenty of water throughout the day.

Local Insights

Hidden Gems

  • Vineyard off the beaten path with panoramic views
  • Secret wine cellar tour in San Gimignano

Wildlife

  • European storks
  • Wild boar in the countryside

History

San Gimignano’s medieval towers once signified power and wealth, with the town thriving during the Middle Ages as a stop on the pilgrim route to Rome.

Conservation

The region actively promotes sustainable farming and preserves its historic architecture to maintain Tuscany’s unique charm.

Frequently Asked Questions

Photography Tips

Best Times

Golden hour in late afternoon
mid-morning for vibrant landscapes

Best Viewpoints

  • Top of San Gimignano’s tallest tower
  • Vineyard overlook near the winery

What to Photograph

Medieval skyline
Rolling vineyards
Stone architecture

Recommended Gear

Comfortable walking shoes

Essential

Sturdy shoes are key for walking through medieval streets and vineyard paths.

Sun protection

Sunblock, hat, and sunglasses help stay comfortable during outdoor activities.

summer specific

Camera or smartphone

Capture scenic vistas and memorable moments throughout the tour.

Water bottle

Essential

Stay hydrated while on the move, especially in warm weather.

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