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Food & Wine of Italy: Tuscany & Umbria

11 days  |  13 days with Rome extension  |  Loading prices

Group size
12–22 travelers
Reviews

4.6 out of 5 stars

426
Activity level
Notice:

From February 15 to April 6, 2026, the city of Assisi will commemorate the 800th anniversary of the death of St. Francis, who was born and died there. For the first time, the Basilica of St. Francis will publicly display his relics: Hundreds of thousands from around the world will make the pilgrimage, and the church will close most of its grounds to accommodate the event. If you’d like to pay homage, be sure to connect with your Tour Director in the Go Ahead app before your trip—they’ll help you determine if it’s possible.

On this tour, coccoli—and baci, and crostini, and more—steal the show.

From endless plains to elegant hilltop towns, Tuscany and Umbria have plenty in common—including a culinary tradition that would make your nonna proud. As you drive with your group across these regions, you’ll find fine wines and humble, time-honored bites at each stop. And don’t overlook those classic sights: Feast your eyes on Florence and Siena (and Rome on the extension) to truly savor this country’s big, bold culture.

Your tour package includes

  • 9 nights in handpicked hotels
  • 9 breakfasts
  • 4 lunches
  • 3 dinners with beer or wine
  • 4 wine tastings
  • 1 cooking lesson
  • 4 tastings
  • 4 sightseeing tours
  • Expert Tour Director & local guides
  • Private deluxe motor coach

Included highlights

  • Mercato Centrale
  • Tuscan cooking lesson
  • San Gimignano
  • Chianti wine tasting
  • Montalcino wine tasting
  • Siena Cathedral
  • Cortona
  • Collegio del Cambio
  • Perugia’s Rocca Paolina
  • Montefalco wine region

Itinerary

Overnight Flight

Day 1: Travel day

Board your overnight flight to Florence today.

Florence

Day 2: Arrival in Florence

Included meal: Welcome dinner

Ciao! Touch down in Italy and transfer to your hotel. Tonight, you’ll get to know your Tour Director and fellow travelers—and set the tone for the coming days—over a three-course dinner at a local restaurant, served with beer or wine.

Rome extension

Rome wasn’t built in a day—and, if you ask us, it wasn’t meant to be enjoyed in a day, either. Whether you play time traveler while hopping between historic sites or live out your best take on “Roman Holiday,” the choice is in your hands, and we’re here to help. Ask your Tour Director for their favorite ways to savor the city—like their secret spot for pasta carbonara—and get going.

Rome

Day 11: Sightseeing tour of Rome

Included meals: Breakfast, Tasting

From the Forum to the Pantheon to the holy confines of Vatican City, Rome bursts with UNESCO-listed landmarks. Today, you’ll follow in the footsteps of the ancients as you explore the capital of modern-day Italy on a guided sightseeing tour.

  • Soak up more than 2,000 years of history in Imperial Rome, viewing the fourth-century Arch of Constantine—the largest surviving Roman triumphal arch.
  • Stop outside the iconic Colosseum, a nearly 2,000-year-old amphitheater that’s both a UNESCO World Heritage Site and one of the Seven New Wonders of the World.
  • Pass the Imperial Fora, the ruins of a series of monumental public squares; the Piazza Venezia, one of Rome’s principal plazas; and the museum-lined Piazza del Campidoglio as you walk to the city’s Jewish Quarter.
  • Step inside a bakery to sample kosher Roman Jewish delicacies, then end your walk at the Porticus Octaviae. Also known as the Portico di Ottavia, this ancient ruin marks the center of the medieval Roman ghetto and was used as a fish market until the 19th century.

The neighborhood of Trastevere is something of a hidden gem—an eccentric, mostly car-free district filled with narrow streets and delectable trattorias. If you choose to add our snack-filled walking tour this afternoon, you’ll explore this art-filled haven while eating your way through pasta, pastries, and gelato. Otherwise, enjoy some free time to yourself (and maybe scope out some landmarks you absolutely want to see).

Day 12: Free day in Rome

Included meal: Breakfast

Master the art of Italian cuisine with an optional pizza-making class today, where you'll learn to stretch dough, select toppings, and bake your creation to perfection before enjoying the fruits of your labor. Or stay in Rome and explore on your own. To try one last marvelous morsel, return to the Jewish Quarter and track down carciofi alla Giudia—simply seasoned, double-fried artichokes

This evening, raise a farewell drink with your groupmates and celebrate a successful trip.

Flight Home

Day 13: Departure

Included meal: Breakfast (excluding early morning departures)

Transfer to the airport for your flight home.

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Hotels

We handpick every hotel to strike the balance of comfort, location, and local charm. Specific accommodations will vary based on your departure date, but these are frequently used hotels for this tour and we're confident you'll be satisfied.

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Umbria - Valle di Assisi

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Florence - Grand Hotel Adriatico

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Siena - Hotel NH Siena

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Rome - Genova Hotel

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Flights

Round-trip flights are one more thing we handle to make your journey as smooth as possible. Our team of travel experts will find the best flight itinerary for you at a competitive rate, thanks to our partnerships with top airlines.

Add our airfare and you’ll get:

  • Round-trip flight for your tour
  • Airport transfers at your destination
  • A great price locked in today
  • 24/7 support from our dedicated service team
  • Options for arriving early, staying longer, or requesting an upgrade
  • Flexible rebooking options if your tour itinerary changes

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