Milan, Oltrepò Winter Time: Craft & Bottle Your Own Wine

If you’re looking for a genuinely immersive wine experience close to Milan, this winter tour in Oltrepò Pavese might just be what you need. While it’s not your typical sightseeing or city tour, it offers a unique chance to connect with local winemaking traditions, taste some fantastic regional wines, and even take home your own bottle.

What makes this experience stand out? We’re big fans of the way it combines hands-on activities like bottling your wine and tasting regional dishes, all set against the backdrop of Italy’s quiet, picturesque countryside. On the flip side, it’s a somewhat specialized outing, so if you’re not into wine or prefer more structured tours, it might not hit all your marks.

This tour is best suited for travelers who crave authenticity, enjoy good food and wine, and appreciate a slower pace. Whether you’re a seasoned wine lover or just curious to try something different during your stay near Milan, this adventure offers a memorable taste of Italy’s lesser-known wine scene.

Key Points

• Authentic experience in Italy’s “Tuscany of the North,” Oltrepò Pavese.
• Hands-on activities like wine bottling and tasting paired with local foods.
• Grape stomping available in August & September—an unforgettable, messy fun.
• Bespoke, intimate tours guided by passionate locals, with flexible itineraries.
• Great value for money with included tastings, food, and a complimentary wine bottle.
• Accessible and suitable for those with mobility considerations, with meeting points and options to be picked up.

You can check availability for your dates here:

Discovering Oltrepò Pavese: Italy’s Hidden Wine Gem

Just 45 minutes from Milan, Oltrepò Pavese isn’t the first destination most travelers consider when exploring Italy, but perhaps it should be. It’s often called the “Tuscany of the North” for its rolling hills, vineyards, and time-lost charm. During winter, the landscape takes on a quieter, more contemplative mood—golden vines, misty valleys, and a peaceful atmosphere that invites you to slow down and savor every moment.

This tour, run by WingsItaly, is all about authenticity. Claire Dymond, the woman behind WingsItaly, has a knack for crafting experiences that go beyond the usual. Instead of a crowded bus tour, you’ll find yourself in small groups, exploring the countryside, visiting family-run vineyards, and tasting wines that truly represent the region’s character. The focus is on local craftsmanship, innovation, and nature, which makes each visit feel personal.

The highlight? The chance to bottle your own wine. Yes, you get to participate in the process—bottling, corking, and taking home a bottle you’ve made. This feature hasn’t gone unnoticed by past guests, with reviews praising the experience’s “fun, messy, joyful, and unforgettable” nature. Plus, a complimentary bottle for every two guests (valid until 2026) makes this a great deal if you’re after something more than just a tasting.

The Itinerary: What You Can Expect

Meeting Up & Setting Off

The tour usually starts with a pickup from specific meeting points near Milan—Casteggio, Pinarolo Po, or Voghera—making logistics straightforward. The meeting points are conveniently located, and options for pickup or meeting on-site provide flexibility.

Exploring the Vineyards

Once on the road, you’ll cruise through hills dotted with vineyards, often shrouded in a gentle winter mist. Here, the guide provides insights into the region’s history and its significance as Italy’s Pinot Nero capital. The small wineries visited are typically family-run, emphasizing tradition and craftsmanship over mass production.

More Great Tours Nearby

Tasting & Food Pairings

A big part of the appeal is the tasting itself. Guests rave about the quality of wines—“great food and even better wine,” according to one reviewer. Expect a selection of roaring reds and winter whites that showcase the region’s diversity. The tastings are paired with regional foods, giving you a full sensory experience that emphasizes local flavors.

Wine Bottling & Take-Home Bottles

One of the most popular features is the wine bottling activity. You’ll learn how to bottle and cork your own wine, then take home a personal souvenir of your day. Past guests mention this activity as “joyful and memorable,” and it’s available until January 6th, making it perfect for holiday travelers.

Optional Activities

If you visit during August or September, you might get to try grape stomping—a messy, fun, and very traditional activity that adds a playful touch to the experience. For those interested, options like pasta making with a local Nonna are available (on request), which further deepen your culture.

What We Loved About This Tour

First, the intimate, guided approach really makes a difference. Claire and her team’s passion for authentic Italian winemaking shines through, making every stop feel personal. The wineries are welcoming, and the tastings are generous and educational.

Second, the opportunity to bottle your own wine is a fantastic keepsake. It’s not just tasting; it’s participating. Many reviews highlight how enjoyable and fun this activity is, particularly for those who want a tangible connection to their experience.

Third, the delicious regional cuisine paired with the wines is a real highlight. You’ll find that the food complements the wines beautifully, enhancing the tasting experience rather than overshadowing it.

Fourth, the value for money is impressive. With tastings, food, a bottled souvenir, and the personalized touch, the experience feels well worth the price. Plus, the flexibility of canceling up to 24 hours in advance and booking without upfront payment adds peace of mind.

The Not-So-Perfect Aspects

While overall this tour receives rave reviews, it’s worth noting that it’s quite niche. If you’re not into wine, the activities might not resonate as much. Also, since it’s a seasonal tour—especially with grape stomping limited to summer—you won’t get every possible activity year-round.

The tour duration is about five hours, which is a good length, but if you prefer more structured or packed itineraries, you might find it a bit relaxed. Lastly, as with any small, artisanal experience, there’s an element of unpredictability—sometimes the wineries may have limited availability or specific schedules.

Who is This Tour Best For?

This experience is ideal for travelers who love discovering authentic local cultures and enjoy tasting regional wines in a relaxed setting. It’s perfect if you want a break from city sightseeing and prefer experiences that are interactive and meaningful. Food lovers, budding wine enthusiasts, or those curious about Italy’s lesser-known wine regions will find this tour especially rewarding.

It’s also suitable for anyone comfortable with a bit of physical activity (bottling isn’t overly strenuous) and looking for something that’s both educational and fun. Even families with older children might enjoy the lively, hands-on nature of the activities, especially during grape stomping season.

FAQs about the Oltrepò Winter Wine Tour

Is the tour suitable for children?
While primarily a wine experience, the activities such as bottling and tasting are generally adult-focused. Grape stomping is seasonal and might be fun for older kids, but it’s not explicitly designed as a family activity.

How long does the tour last?
It runs for about five hours, making it a manageable half-day outing that leaves plenty of time for relaxation and exploring on your own afterward.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours before the tour for a full refund, providing flexibility if your travel plans shift.

Are there options for pickup or do I need to meet at the designated points?
You can be picked up from designated meeting points in Casteggio, Pinarolo Po, or Voghera, or meet the tour at these locations. The host can arrange pickups, which adds convenience.

Is this experience accessible for people with mobility issues?
Yes, the tour is wheelchair accessible, making it more inclusive for those with mobility considerations.

What does the wine tasting include?
Guests are treated to extensive wine tasting paired with local foods, showcasing the region’s best reds and whites.

When is the grape stomping activity available?
Grape stomping is available only in August and September, so if that’s a must-do, plan your visit accordingly.

Is the wine bottled during the tour good quality?
Guests consistently praise the wines, noting they’re representative of the region’s craftsmanship and quality.

Final Thoughts

If you’re after a relaxed, authentic introduction to Italy’s wine culture, this tour hits the mark. It’s more than just a tasting; it’s a full sensory journey into the heart of Oltrepò Pavese’s winemaking traditions. The hands-on element, the warmth of local families, and the stunning winter scenery come together to create a memorable day.

Ideal for curious travelers, food and wine lovers, or anyone seeking a meaningful escape from busy city life, this experience offers a rare look into Italy’s soulful wine regions. While it may not be for everyone—especially if you’re not into wine or prefer structured, packed itineraries—it’s a treasure for those who want to slow down and connect with Italy’s rural charm.

In short, WingsItaly’s winter tour combines authenticity, craftsmanship, and genuine hospitality. It’s a chance to create your own wine story and enjoy the quiet beauty of northern Italy’s countryside, all within easy reach of Milan.

You can check availability for your dates here: