ROMANTIC WINE TOUR FOR 2 – Wine Tour in Chianti (Tuscany)

Imagine sipping Vernaccia white wine or Chianti Classico with rolling hills as your backdrop—this private tour promises just that. Designed for couples, honeymooners, or those celebrating special milestones, this experience offers a taste of Tuscany’s best wines, scenery, and small-town charm all in one day. It’s the kind of trip that combines the pleasures of wine, food, and history, with just enough guided insight to make you feel like a seasoned connoisseur.

What we love about this tour is how personalized and carefully curated it feels—visiting two different wineries with meals included at one, and exploring the medieval town of San Gimignano with its famous towers and gelato. The second thing that makes it stand out is the focus on authentic Tuscan cuisine paired with a variety of more than 10 wines, from Supertuscan blends to Vin Santo. The only potential downside? For those with limited mobility, climbing the 200 steps of San Gimignano’s Great Tower might be a challenge, as there’s no elevator.

All in all, this tour is ideally suited for travelers who want a luxurious, intimate experience blending wine, history, and scenic beauty while enjoying the comfort of a private guide. If you’re after a well-rounded, authentic taste of Tuscany that’s perfect for a romantic getaway, this could be just the ticket.

Key Points

• Private experience tailored for couples and small groups, offering personalized attention.
• Two winery visits with tastings, including cellar tours and an authentic Tuscan meal.
• San Gimignano visit with free time to explore, shop, and enjoy gelato.
• Diverse wine selection with over 10 varieties like Chianti, Supertuscan, and Vin Santo.
• Scenic drive and panoramic stops at Michelangelo Square with views over Florence.
• Comfortable private transportation for a relaxed, hassle-free day.

You can check availability for your dates here:

The Itinerary: A Well-Curated Journey

This tour begins with a pickup directly from your Florence or surrounding area location, making it exceedingly convenient. Expect to depart around 9:30 am, giving you a full 8-hour experience that balances sightseeing, tasting, and relaxing. The journey kicks off with a scenic 1.5-hour drive into the Chianti countryside, where stunning vistas of rolling vineyards and olive groves set the scene for the day.

The first stop is a photo opportunity and guided visit in Tuscany, where you’ll get a glimpse of the landscape’s unique charm. We loved the way the driver-guide smoothly combines commentary with the scenery—making the drive itself part of the experience. You’ll have a chance to sample the best Tuscan wines—more than 10 different varieties, including Chianti, Chianti Classico, Chianti Riserva, and White Pinot—each offering a different taste of this renowned region.

Next, you’ll stop for a lunch that’s more than just a quick bite—an authentic Tuscan meal featuring cold cuts, prosciutto, and fresh homemade pasta. This part of the tour isn’t just about the wine; it’s about tasting the local flavors in a setting that feels genuine. The reviewers praise the quality of food and wine, with one noting, “We experienced wine tasting at two wineries and had lunch at one. It was a perfect day.”

Winery Visits: More Than Just Tasting

Visiting two different wineries is the core of this experience. These visits typically include guided tours of the cellars and vineyard areas—valuable for understanding the craftsmanship behind each bottle. You’ll get to taste an array of wines, from Chianti DOCG and DOC to Supertuscan blends, and even Vin Santo, a sweet “Holy Wine” that’s a Tuscan staple. Reviews indicate that guides at these wineries are knowledgeable, adding context and making the tastings educational as well as enjoyable.

One guest noted, “The wineries he took us to were incredible,” emphasizing the quality of these visits. Given the variety, you’ll get a broad sense of Tuscany’s winemaking styles, from crisp whites like Vernaccia to full-bodied reds. If you’re a wine enthusiast, this is a highlight worth paying for.

The Charm of San Gimignano

After the wineries, the tour takes you to San Gimignano, often called the “Medieval Manhattan” thanks to its skyline of distinctive towers. The town’s UNESCO World Heritage status and well-preserved architecture make it a must-see. Here, you’ll have free time for shopping, sightseeing, and indulging in the town’s legendary gelato—famous enough to have won an international contest. One reviewer mentioned, “We bought souvenirs and had gelato, which was the best I’ve ever had,” illustrating how delightful this stop can be.

Climbing the Great Tower is optional but worth it for panoramic views of Tuscan hills and the surrounding countryside. Be prepared for 200 steps—no elevator—and remember, it’s a steep climb, but the view from the top makes it worthwhile.

Scenic Highlights and Free Time

Throughout the day, your guide will make stops at Michelangelo Square, offering a panoramic view of Florence, perfect for photos. The scenery alone is worth the trip, and the relaxed pace allows you to really savor the moment. The drive back to Florence wraps up around 6 pm, giving you a full day of memorable sights, flavors, and experiences.

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Transportation and Comfort

Travel is in a private Mercedes van or similar, ensuring comfort and personal space. The private driver-guide makes everything seamless, handling logistics so you can focus on enjoying each moment. The tour is wheelchair accessible, a big plus for travelers with mobility concerns.

Price and Value

At $677.54 for two people, this tour might seem a bit of an investment, but the value lies in the personalized experience, quality of tastings, scenic stops, and included meals. If you consider the cost of private transfers, guided tastings, and a full day of sightseeing, it’s a good deal for those seeking a relaxed, upscale experience.

This experience is ideal for romantic couples or honeymooners wanting a special day in Tuscany. It’s also perfect for food and wine lovers eager to broaden their palate with authentic regional varieties. If you’re interested in medieval towns and stunning vistas, San Gimignano will surely impress.

Travelers who prefer a stress-free, all-in-one day trip—including transportation, guides, tastings, and meals—will find this tour offers excellent convenience and a memorable experience. However, those with mobility issues should be aware of the 200-step climb at San Gimignano.

This private Chianti wine tour offers a finely balanced mix of scenic beauty, authentic cuisine, and excellent wine. The guided visits to two wineries provide insight and education, while the opportunity to explore San Gimignano adds a dash of medieval magic. The scenic drives, panoramic stops, and well-chosen tasting locations make it a comprehensive way to experience Tuscany’s renowned landscape and flavors.

The tour’s focus on personalized service and authentic experiences makes it ideal for those celebrating something special or simply wanting a luxurious, intimate day. The reviews highlight knowledgeable guides, stunning views, and superb wine selections—all crucial ingredients for a memorable trip.

If you’re after a day that combines delicious food, fine wine, and a chance to soak up the Tuscan atmosphere, this tour deserves serious consideration. For travelers who want a taste of Italy without the hassle of planning, it’s a practical, enjoyable, and genuinely authentic choice.

Is this tour suitable for couples?
Yes, it’s designed specifically for couples, offering an intimate, private experience perfect for celebrating special moments.

What wines are included in the tastings?
You’ll taste more than 10 different varieties, including Chianti, Chianti Classico, Chianti Riserva, Supertuscan, White Pinot, and Vin Santo.

How long does the tour last?
It’s an 8-hour experience, starting around 9:30 am and returning by early evening.

Is transportation private?
Yes, transportation is in a private Mercedes van or similar, with a private driver-guide.

Are meals included?
Yes, a full Tuscan meal is included at one of the wineries, featuring local cold cuts and homemade pasta.

Can I visit San Gimignano’s towers?
You have free time in San Gimignano to explore, shop, and climb the Great Tower (200 steps). It’s optional but highly recommended for the views.

This tour offers a great blend of wine, scenery, history, and authentic Tuscan feeling. Whether you’re seeking a romantic escape or a rich introduction to Italy’s wine country, it’s a choice that promises plenty of memorable moments—at a pace that allows you to savor it all.

You can check availability for your dates here: