Travel to Tuscany with Shumacher Wines
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Join Katie & Ryan Shumacher for a hosted wine retreat in Italy for a week of villa living, chef-prepared meals, small family-run winery visits, medieval hill towns, cooking classes, and shared meals around the table.
May 5-11, 2027 | 7 Days | Maximum 18 Guests
Buongiorno! We are so excited to invite our Shumacher Wines club members and friends to join us for a week in Italy next May 2027.
Tuscany has always held a very special place in our lives. We both studied abroad there together in college, and since then we have returned to Italy many times over the years—drawn back again and again by the food, the wine, the landscape, and the way life seems to slow down around the table. It is one of our favorite places in the world, and it is also where we first truly fell in love with wine, and is a big part of why we wanted to make a Sangiovese of our own. Long before Shumacher Wines existed, some of our most memorable wine experiences happened in Tuscany, and this trip is our opportunity to share those experiences with you.
Together, we’ll spend a week in a villa between Umbria and Tuscany, surrounded by vineyards, olive groves, medieval hill towns, and the beautiful views of Lake Trasimeno. We’ll visit family-run wineries, gather for chef-prepared meals, explore historic towns, and experience the region through the people who know it best.
Ryan and I will be traveling with the group as your Shumacher Wines hosts, tasting alongside you, sharing meals, talking through the wines and regions we visit, and helping create the kind of relaxed, thoughtful, wine-centered experiences we love to bring to our own events. We are partnering with Lucia, Lizzy, and Giulio, whose local knowledge, relationships, and hospitality expertise make this trip possible.
Ryan & Katie in Tuscany almost 20 years ago!
Itinerary
Day 1
Arrival Day
After landing at Rome Fiumicino Airport, we’ll be greeted by our private driver and make our way to our home for the week: Di Colle in Colle, a beautiful agriturismo in Umbria just across the Tuscan border. Set above Lake Trasimeno, the property is surrounded by vineyards and countryside, with a pool, sweeping views, and a warm, traditional restaurant where many of our meals will be prepared by a private chef.
That evening, after everyone has had time to settle in, we’ll come together for our first tasting with Giulio, the villa owner and winemaker. Giulio farms the vineyards around the property organically and produces small-production wines. We’ll enjoy his wines alongside a relaxed three-course dinner prepared by our chef.
Brunello
We’ll begin the day with a private guided tour of Pienza, a beautiful hilltop town known for its Renaissance architecture, sweeping valley views, and rich history. After the tour, you’ll have free time to wander the town, shop, and enjoy lunch at one of the many incredible osterias.
From there, we’ll head into Brunello country for a private visit and tasting at a family-owned winery. Brunello di Montalcino is considered one of Italy’s most celebrated wines, and this experience will showcase a deeper look at the land, tradition, and craftsmanship behind it.
After we return to the villa, you’ll have time to relax, freshen up, or enjoy a cocktail before we gather again for another chef-prepared three-course meal and thoughtfully paired wines.
Day 2
Montepulciano
We’ll start the day with a private guided walk through Montepulciano, one of Tuscany’s most striking hilltop towns and one of our favorite places in Italy. After the tour, you’ll have free time to browse the boutiques and wine shops, explore at your own pace, and enjoy lunch in town.
In the afternoon, we’ll visit a family-owned estate that specializes in the famous Vino Nobile di Montepulciano.
Back at the villa, take some time to unwind with a sunset aperitivo while enjoying the lake views. Later, we’ll gather for a three-course dinner prepared by our chef, paired with plenty of local wine.
Day 3
Day 4
Pasta Making Class & Truffle Hunting
We’ll spend the day at Lucia's historic estate for a private truffle hunting experience, led by a local expert and a trained truffle dog. After a gentle walk through the woods in search of truffles, we’ll learn more about this regional delicacy and enjoy a guided tasting.
Next up is a hands-on pasta-making class. We’ll learn how to prepare fresh pasta from scratch, then sit down together for lunch on the patio, paired with local wine. After lunch, we’ll continue the afternoon with a tasting of regional olive oils.
Back at the villa, we’ll wind down with a sunset walk through the vineyard with Giulio. He’ll share more about the vines surrounding the property as we take in the views over the lake. The day will close with another chef-prepared three-course dinner and plenty of wine around the table.
Day 5
Chianti
We’ll begin the day with a private guided tour of Siena, one of Tuscany’s most beautiful and historic cities. Our visit will include the Basilica Cateriniana di San Domenico as well as the unforgettable Piazza del Campo, the grand central square where the Palio horse race has taken place for centuries. After the tour, you’ll have time to enjoy lunch, browse the shops, and explore Siena at your own pace.
In the afternoon, we’ll make our way into Chianti Classico for a truly special winery visit. This small, family-run estate is considered the smallest winery in Chianti Classico, producing only around 2,000 bottles each year. Now run by the 6th, 7th, and 8th generations of the same family, the winery feels more like being welcomed into someone’s home than visiting a tasting room. We’ll tour the vineyard and taste wines that are rarely shared outside the family, making this one of the most intimate and memorable stops of the week.
We’ll return to the villa for our favorite evening rhythm: sunset spritzes, time to relax, and a chef-prepared three-course dinner with plenty of wine around the table.
Day 6
Cortona
We’ll spend the morning in Cortona, a beautiful Tuscan hill town many people know from Under the Tuscan Sun. After the tour, you’ll have free time to wander the shops, stop for gelato, or settle in for lunch at one of our favorite local spots.
In the afternoon, we’ll explore a different side of Tuscan wine. Unlike many of the surrounding regions, Cortona is especially known for international varieties rather than Sangiovese, including Syrah and Cabernet Sauvignon. We’ll visit a winemaking family at their home for a private tasting and a closer look at the wines they produce.
Our final evening at the villa will bring the week full circle. Dinner will feature a selection of the wines we tasted throughout the retreat, paired with a special multi-course meal prepared by our chef. It will be a relaxed, memorable way to toast the end of our week together in Tuscany.
Day 7
Departure
After breakfast, our private English-speaking drivers will take us back to Rome Fiumicino Airport for your journey home. Arrivederci!
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