Taste of Italy: Tuscany & Umbria

Itinerary

• Day 1: Overnight flight

  Board an overnight flight to Milan and get some rest. The debate between bucatini and rigatoni can wait a few more hours.

• Day 2: Arrive in Milan + Welcome Dinner

  And just like that, you’re in Italy. Food is going to be a common theme on this trip, but before you start all that eating…nevermind, it’s Welcome Dinner time. Mangia!

  Today's highlights:

  • Land at the airport and meet an EF representative.
  • Transfer to your accommodations and check in.
  • Meet your Tour Director and get deets on tomorrow’s schedule.
  • Head to a local spot for an included dinner with your group.
• Day 3: Explore Milan

  Milan is a city where old meets new, where fashion is king, and where risotto alla Milanese is the house specialty just about everywhere. Today, you’ll see each side of the city with a local guide.

  Today's highlights:

  • Admire the architecture of the Milan Cathedral—the largest church in Italy.
  • Browse the luxury shops at the Galleria Vittorio Emanuele II.
  • See the medieval Castello Sforzesco and learn its history.
• Day 4: Travel to Bologna via Parma

  You’re off to Bologna, the largest city in and capital of the Emilia-Romagna region. But first, a pitstop in Parma—a UNESCO City of Gastronomy (nbd).

  Today's highlights:

  • Seek out the best prosciutto di Parma and Parmigiano Reggiano, right at the source.
  • Visit the impressive(ly old) Parma Cathedral—built in 1106.
  • Continue to Bologna, your home for the next couple of nights.
• Day 5: Sightseeing in Bologna

  Let’s explore Bologna—NOT pronounced ba·lo·ney, but home to the charcuterie staple otherwise known as mortadella. So, there’s that.

  Today's highlights:

  • Stop by the University of Bologna, the oldest university in the world.
  • Walk (and eat) your way through the city’s fish and veggie markets.
  • Watch the world go by from a cafe in bustling Piazza Maggiore.
• Day 6: Travel to Tuscany via San Gimignano and Monteriggioni

  Your next stop is Tuscany, a region known for its rolling hills, lush valleys, and historic cities. Before arriving in the southern Tuscan region, visit two medieval cities to taste local bites and sip wine exactly where the grapes are grown.

  Today's highlights:

  • Wander Monteriggioni, a small commune surrounded by its original walls.
  • Tour San Gimignano, known for its 14 towers overlooking the countryside.
  • Sip wine at a Chianti estate outside of San Gimignano.
  • Eat gelato. All of it.
• Day 7: Tour Siena + wine tasting

  This day is just quintessential Tuscany, folks. Sightsee your way through Siena with a local guide, visiting its 13th-century city center—a UNESCO World Heritage Site.

  Today's highlights:

  • Enjoy a pastry tasting and lunch while touring Siena.
  • See the Piazza del Campo, Siena’s iconic square.
  • Stop in charming Montalcino for a wine-cellar tour and Brunello tasting.
• Day 8: Free day in Tuscany + optional Civita & Lake Bolsena day trip

  Art? Architecture? Amatriciana? Choose your own adventure, because today is yours to take on Tuscany however you want.

  Free time suggestions

  Pisa: You may have seen photos from this place before. You know, of the giant Leaning Tower that anyone and everyone poses in front of. Could be you.

  Saturnia hot springs: Free to visit 24/7/365, these natural hot springs are a great place to unwind. Try shooting for sunrise or sunset, when crowds are minimal.

  Civita & Bolsena Lake day trip (extra cost)

  Explore the surreal Civita di Bagnoregio, a hilltop village accessible by footbridge. Then, head to Lake Bolsena and enjoy lunch during some free time.

• Day 9: Head to Umbria via Pienza & Montepulciano + wine tasting

  Time to head south to Umbria, a region known as Italy’s green heart. And let’s make a day out of the trip with some wine, cheese, and wine…and more cheese.

  Today's highlights:

  • Visit Pienza to taste local pecorino cheese and grab some lunch.
  • Tour a Montepulciano winery and taste their vino nobile.
  • Arrive in Umbria and get settled in to your accommodations.
• Day 10: Free day in Umbria + optional Assisi day trip + Farewell Dinner

  The day is yours. Feel free to see Umbria at your own pace. In the evening, share some laughs (and maybe shed a few tears) at an included Farewell Dinner with your group.

  Free time suggestions

  Lake Trasimeno: Lake Como’s little cousin, Trasimeno boasts some magical waterfront towns as well as a few islands you can visit and explore.

  Truffle hunting: Join a guide and their skillfully trained dog (bonus points you get to hang with a dog) to seek out the finest Umbrian truffles.

  Tour Assisi (extra cost)

  Explore Assisi with a guide, then visit a local farm for lunch and a tour of its vineyard, olive grove, and winery.

• Day 11: Travel to Rome via Orvieto

  Rick Steves (the GOAT travel writer) said Orvieto is “what an Italian hill town should be.” On your last day in Italy, you’re gonna find out why.

  Today's highlights:

  • Visit Orvieto for one last Italian lunch and some time to explore.
  • Peep the medieval architecture situated on a large butte of limestone.
  • Head to the Rome area for one final sleep near the airport before you return home.
• Day 12: Fly home

  Arrivederci, amici!  
  Translation: goodbye, friends! Your next destination awaits—home. But this isn’t goodbye. It’s “See you later.” The only question is, where?