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Holiday Magic in Italy


NEW! Join us in Italy for a holiday trip that avoids the major tourist hubs. Experience the magic of Italy in December.

This special holiday trip invites you to discover cherished Italian traditions—from Christmas markets and nativity scenes to regional feasts and sweet holiday treats like panettone and torrone.

We’ll begin in Tuscany, where Florence invites you to soak up Renaissance art, elegant architecture, and the joy of the city’s holiday atmosphere. Stroll through markets filled with artisanal gifts, taste regional specialties like panforte and vin santo, and enjoy the warmth of Italian hospitality. The Tuscan countryside, with its cozy villas and vineyards, offers a serene backdrop for winter wine tastings and fireside dinners.

In Umbria, often called Italy’s “green heart,” you’ll discover the region’s authentic traditions and quieter pace. Medieval hill towns such as Assisi, Perugia, and Orvieto take on a magical glow during December, with festive concerts, artisan fairs, and seasonal cuisine that highlights local truffles and hearty wines. This is also the perfect chance to shop for one-of-a-kind gifts—from hand-painted ceramics to gourmet delicacies—while experiencing Italy’s most cherished holiday customs.

Explore charming towns dressed for the season, and savor the warmth of Italian hospitality during one of the most joyful times of year. It's also the perfect opportunity to shop for one-of-a-kind gifts, including artisanal crafts, gourmet delicacies, and handmade treasures you won’t find anywhere else.

By the time your journey comes to an end, you’ll have celebrated the season Italian-style: with incredible food, fine wine, cultural treasures, and unforgettable moments. Tuscany and Umbria in December offer a rich blend of beauty, tradition, and joy—an ideal way to embrace the holidays and close the year with memories you’ll cherish forever.


What’s Included:

  • Accommodations: 4-star boutique hotels, wine resorts, restored castles and villas.

  • Private guided tours.

  • Special insider activities that could include food and wine experiences, truffle hunting, visits to wine and food producers, and more.

  • All entrance fees to museums and other sites.

  • All ground transportation between destinations. (Does not include transportation, such as taxis, to and from airports and not described in the itinerary.)

  • Meals included as noted in itinerary.

  • Guide and driver tips.

What’s Not Included:

  • Airfare

  • Travel Insurance

  • Personal Expenses

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October 5

Sicily and Malta