Italy: A Curated Journey Through Le Marche & Umbria

April 16–23, 2027

Some places stay with you long after you've left.

For me, Italy has always been one of those places.

Years ago, I lived in Northern Italy, spent time working in Florence, explored the Amalfi Coast by car, and wandered the streets of Rome whenever I could. Those experiences shaped the way I think about hospitality, food, wine, craftsmanship, and the beauty of slowing down.

Now, I'd love to share that feeling with you.

Prinsley Journeys was created for people who want more than a vacation. These are thoughtfully curated experiences centered around authentic places, exceptional food and wine, meaningful conversations, and genuine connection.

Our inaugural journey takes us to Le Marche and Umbria—two of Italy's most beautiful yet often overlooked regions. Together with our trusted Italian partners at Ciao Andiamo, we've designed an itinerary that balances discovery, relaxation, and unforgettable local experiences.

Over seven days we'll visit family-owned wineries, stroll through medieval villages, enjoy regional cuisine, unwind at one of Umbria's renowned thermal spas, meet local artisans, and experience Italy at a pace that invites you to truly be present.

Highlights

• Boutique winery visits and private tastings with local producers

• Charming villages and breathtaking countryside

• Regional food experiences and unforgettable meals

• Guided visits to Assisi and Ascoli Piceno

• Relaxation at a world-class Umbrian thermal spa

• An exclusive visit to a local cashmere workshop

• Beautiful four-star accommodations

• Private transportation throughout the journey

• Plenty of time to wander, shop, explore, or simply enjoy a leisurely aperitivo

This is not about checking destinations off a list.

This trip is all about lingering over lunch, discovering hidden places, meeting the people behind the wine, and experiencing Italy with curiosity and intention.

Small Group & Private Experiences

Prinsley Journeys are intentionally intimate.

Join one of our scheduled small-group departures, or let us create a private experience for your family, friends, wine club, or corporate group. Each itinerary can be customized to match your interests, whether your focus is wine, wellness, food, culture, craftsmanship, or simply enjoying la dolce vita.

Is This Journey for You?

If you appreciate exceptional hospitality, beautiful landscapes, incredible food and wine, authentic cultural experiences, and traveling beyond the typical tourist path, you'll feel right at home.

Whether you're a longtime Prinsley supporter or discovering us for the first time, we'd love to share Italy with you.

Join the Interest List

Our Spring 2027 journey has limited availability.

To receive pricing, the complete itinerary, and reservation details, join our interest list or contact us directly.

We'd love to help you experience Italy through the Prinsley lens.