Erik Segelbaum Presents

An Insider’s Food & Wine Journey

Southern Tuscany & Umbria

September 21–27, 2026 | 6 Nights

Join us for an intimate exploration of Southern Tuscany and Umbria. We will be based in the enchanting hilltop town of Montepulciano.

Our home for the week will be beautifully restored palazzos in the very heart of Montepulciano, offering both comfort and a true sense of place. From this base, we’ll immerse ourselves in the region’s extraordinary food, wine, and culture.

Picture medieval hill towns with sweeping views, glasses of world-class wine enjoyed against the backdrop of rolling Tuscan countryside, and cuisine that captures Tuscany at its finest. Over the course of the week, we’ll visit some of Italy’s most celebrated wine regions, including:

• Orvieto

• Vino Nobile di Montepulciano

• Brunello di Montalcino

• Chianti Classico

Each day brings curated excursions for wine tastings, memorable meals, and cultural discoveries. Evenings are yours to enjoy at your own pace—wander Montepulciano’s quiet streets, watch the sun set over the hills, or continue your personal eating and drinking adventure at one of the town’s excellent restaurants and wine bars.

A relaxed, insider experience in one of Italy’s most captivating regions—designed for those who love great wine, authentic food, and the pleasure of traveling well.

Our journey begins at 10:00 AM at Eataly, an easy and convenient meeting point near the Ostiense train station. Please meet us in front of the main Eataly entrance. The location is approximately 15–20 minutes from central Rome, and we’ll share a link with the exact address in advance. Guests should arrange their own transportation from their prior accommodations to the meeting point.

From there, we head north toward Tuscany, but first we will stop in the spectacular hilltop town of Orvieto. Here, we’ll enjoy an unforgettable outdoor lunch with Giovanni, perfectly paired with local wines, followed by time to wander Orvieto’s atmospheric streets and admire its magnificent Duomo, one of Italy’s true architectural treasures.

By late afternoon, we arrive in Montepulciano, where we’ll check into our accommodations in the heart of this historic town—our home for the days ahead and the beginning of our Tuscan adventure.

A Taste of Place
Get to know your home base, Montepulciano—its rich history, stylish little shops, sweeping views over the Val d’Orcia, and ancient Etruscan wine cellars hidden beneath the town’s streets.

Eating Well
We will enjoy a beautiful lunch with Virginia and her father, Massimo, set within the historic walls of the city. We will have exclusive use of all the tables in this small, elegant space.

Wine Tasting
Today we will taste the elegant Vino Nobile in Montepulciano.

Wine & Lunch

Today we will enjoy a wine tasting followed by a home-cooked lunch in the renowned Brunello di Montalcino region.

A Touch of Culture
You may recognize La Foce from its cameo in a wedding scene on HBO’s Succession, but its fame barely hints at its true magic. These extraordinary gardens are a rare and tranquil masterpiece—elegant, timeless, and quietly breathtaking. A visit here isn’t just recommended; it’s essential.

A Dose of Culture
Step into the medieval soul of Siena. Join a guided walk through its storied streets or explore on your own, letting the city unfold at your pace—Gothic beauty, hidden corners, and centuries of history around every turn.

Wine Tasting
After exploring Siena, we’ll venture into the heart of Chianti Classico to visit one of Erik’s favorite producers.

Eating Well
We’ll enjoy a light, delicious lunch at our favorite spot in Siena, featuring pecorino, charcuterie, marinated artichokes, fresh salads, bruschetta, and perhaps some homemade meatballs, paired with local wines.

A Taste of Culture
Spend a relaxed afternoon wandering the irresistibly charming village of Pienza. With its picture-perfect streets, sweeping Val d’Orcia views, and timeless beauty, don’t be surprised if you start imagining this as the location of your future Italian home.

Dinner Together
This evening, we reconvene in Montepulciano for a memorable group dinner hosted by the ever-entertaining Maurizio—an evening of excellent food, flowing wine, and plenty of laughter to cap off the day.

Cooking Class, Lunch & Wine Tasting
We head to a breathtaking countryside setting near Cortona, the village made famous by Frances Mayes in Under the Tuscan Sun.

Here, we’ll roll up our sleeves for a hands-on cooking class, followed by a leisurely lunch showcasing the dishes we’ve prepared, perfectly paired with local wines. A joyful, flavorful celebration of Tuscan cooking, scenery, and the simple pleasures of life.

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.