Catoctin Creek Distillery presents
An Insider’s Food & Wine Journey through Southern Tuscany & Umbria

From our base in the hilltop town of Montepulciano

May 10 - 16, 2027

Spend six unforgettable nights in the heart of Montepulciano, surrounded by breathtaking landscapes and steeped in Italian charm.

Picture yourself exploring medieval hilltop towns, sipping world-class wines as you gaze across the Tuscan countryside, and savoring authentic regional cuisine at its finest.

Our journey will take us through some of Italy’s most celebrated wine regions — Orvieto, Vino Nobile di Montepulciano, Brunello di Montalcino, and Chianti Classico.

We’ll be based in a beautifully restored palazzo in the extraordinary town of Montepulciano. Each day brings a new adventure of wine, food, and culture — and each evening is yours to enjoy as you wish: wander the quiet cobblestone streets, watch the sun set over the rolling hills, or continue your culinary discoveries well into the night.

Our adventure begins at 10 AM at Eataly, a convenient meeting point near the Ostiense train station. Look for us in front of the main entrance to Eataly. The location is about 15-20 minutes from central Rome, and we will share a link with the exact address. Please arrange your own transportation from your prior accommodations to the meeting point.

From there, we’ll set off for Tuscany, stopping in the stunning hilltop town of Orvieto for an unforgettable outdoor lunch with Giovanni, paired with excellent local wines. Afterward, we’ll explore Orvieto’s charming streets and visit its breathtaking Duomo.

We will arrive in Montepulciano in the late afternoon and check in to our accommodations in the heart of this historic town.

A little culture – You will get to know your base of Montepulciano – history, cool shopping, breathtaking views and ancient Etruscan wine cellars.

Eating – Lunch will be an unforgettable experience with Silvio, just outside Montepulciano. Silvio is the ultimate entertainer, while his mother works her magic in the kitchen, serving up authentic Tuscan dishes in a warm and lively atmosphere.

Wine tasting – In the afternoon, we’ll visit Olimpia at her picture-perfect winery, Le Bertille. Nestled just down the hill from Montepulciano, this small, family-run estate produces exquisite Vino Nobile, offering an intimate and authentic tasting experience

Wine & lunch – Enjoy an intimate tasting of the world-famous Brunello di Montalcino with Gianluca and his wife Kai at their small family-run winery, Santa Giulia. Then, we get to sit down for a delicious home-cooked meal with the family, lovingly prepared by Gianluca’s mother, Nonna Mirella.

A little culture – It had its moment of fame during a wedding scene in the HBO series Succession. but the gardens of La Foce are a true hidden gem in their own right. A visit here is an absolute must.

A little culture – Explore the medieval charm of Siena with a guided tour, or simply wander its historic streets at your own pace, soaking in the beauty of this timeless city.

Wine tasting – We will meet up with Andrea of I Sodi winery at his family’s incredible vineyard in the historic Chianti Classico district. Most people say this is their favorite winery visit of the tour, and that is really saying something!

Eating – Lunch will be a light and delightful affair in Siena at Pretto, where we’ll savor local specialties and wine. Back in Montepulciano, we’ll wind down with a comforting bowl of traditional Tuscan soup and a glass of wine, shared with our dear friend Cristina.

A little culture – This is a relaxing afternoon to explore the village of Pienza. You may even consider purchasing your next residence in Pienza after spending an afternoon here.

Cooking class, lunch and wine tasting – We are going to have a cooking class and lunch at a stunning location just down the road from Pienza, facing the largest mountain in this part of Tuscany.

Wine tasting – Enjoy a special tasting of Goretti’s wines in the picturesque village of Panicale, a wonderful way to discover Umbria’s unique grape varieties.

A little culture – Panicale had its moment in the spotlight when it was featured in The New York Times, and today, you’ll experience firsthand what makes this village so special.

Lunch – A meal at Cucina Rastrello may just make this your new favorite restaurant in Italy.

We will drop you off in Florence—either at the airport or the Santa Maria Novella train station— by noon, ready for you to continue your Italian adventure.