Tuscany & the Italian Countryside | EF Ultimate Break
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Tuscany & the Italian Countryside

5 Cities

Travel Style:

Why Go?

Name a better duo than wine and cheese, we’ll wait. There may be no better combo, and nowhere is it easier to kick back with a block of pecorino, some prosciutto di Parma, and a bottle of chianti, than in the Tuscan countryside. Oh, and don’t get us started on that view! This trip will take you to the hillside towns that are as fun to say as they are to visit (looking at you, Montecatini), but it also touches on the big cities like Rome, Florence, and Milan for a taste of high culture. This is the land of vineyards, the cobblestone streets of your running-away-to-Europe-forever fantasies, and the birthplace of drinking wine that was grapes, like, yesterday. If there is indeed a better combo than wine and cheese, it must be Tuscany and you.

What are the top highlights?

  • Indulge in wine tastings in all sorts of rustic locations, including within a medieval Tuscan village
  • See a bunch of Bologna—a city known for eating and educating
  • Step into medieval times in Siena and the walled town of San Gimignano
  • Picnic on the freshest cheeses and meats you’ve ever feasted your eyes on
  • Tour the oldest university in Europe, maybe even apply there if you want to
  • Have your own personal Renaissance in Florence
  • Eat all of the gelato in Rome
  • Kick back in the Tuscan countryside for some serious #views

Your trip includes

  • Round-trip flights & airport transfers
  • Multilingual Tour Director & local guides
  • Private motorcoach
  • 10 nights in hand-picked accommodations
  • Welcome Dinner with food & drinks
  • Daily breakfast & three-course Farewell Dinner
  • Entrances to select attractions


You’ll stay at accommodations hand-picked by our team of local experts, in rooms only for EF Ultimate Break travelers. Each property is located in a safe, convenient area. You’ll receive your exact accommodations 30 days before your trip departs.

Click here for examples of where you'll stay.


Admit it, booking flights is the worst. Here's why you should let us do it for you:

  • Flight costs are included in your monthly payment plan, so you can pay over time
  • Airport transfers are included, so we’ll be waiting, sign in hand
  • Flights are booked with major airlines
  • 24/7 support no matter what time zone you’re in
  • One checked bag included on most flights
  • Option to make changes to your trip up to 99 days before departure

Booking with a friend? Let us know and we’ll do our best to make sure you’re on the same flight. Still want to book your own flights? That’s cool, simply select ‘No flights included’ instead of your departure city in the ‘Flights from’ dropdown.


    Day 1: Overnight Flight

    Hop on your overnight flight to Milan. If you haven’t heard, you’ll be spending quite a bit of time in Tuscany, where gorgeous landscapes, gorgeous food, and—wait for it—gorgeous wines are patiently waiting for you to arrive.

    Day 2: Arrive in Milan

    Welcome to Italy! Your first stop is Milan, the design, fashion, and commerce center of the country. It won’t take you long to find Milan’s impressive Gothic Cathedral, which took nearly 600 years to build. It’s the largest church in Italy—yes, in the entire country—and it’s pretty hard to miss.

    Today's Highlights:

    • Land at the airport and meet a waiting EF representative.
    • Transfer to your hotel to check in and check out your room.
    • Get familiar with the area around your hotel with an introductory walk with your Tour Director.

    In the evening, it’s time for your Welcome Mixer. Enjoy some appetizers over drinks with fellow travelers at an authentic local spot. Then it’s on to wherever your new friends and the party take you.

    Day 3: Travel to Bologna via Parma

    You’re on the move, but trust us, this is a good thing. You’re headed to Bologna. But first, you’ll stop in the city of Parma, where a celebrity awaits. Perhaps you’ve heard of them…parmesan cheese. And its celebrity sidekick, prosciutto di Parma (AKA drool-worthy ham).

    Today's Highlights:

    • Hop on the bus and make your way toward Bologna.
    • Follow your nose in the general direction of parmesan cheese during an included stop in Parma, Italy.
    • Arrive in Bologna and check in to your accommodation.

    Day 4: Tour Bologna

    Welcome to the hidden gem of Italy: Bologna. Known for pasta, the (surprisingly large) mortadella sausage, and Europe’s oldest university, the city is buzzing with energy. Get to know it with a local guide and discover how Bologna’s culture and cuisine come together to create the perfect Italian city.

    Today's Highlights:

    • Tour the University of Bologna, the oldest and one of the most prestigious universities in Europe.
    • Embrace the sights, sounds, and definitely the smells of a fish and vegetable market.
    • Soak in the medieval and Renaissance vibes at Piazza Maggiore, Bologna’s main square.

    Day 5: Travel to Montecatini via Florence

    Get up, board the private bus for a short drive, and then step out in the beautiful city of Florence. Join a local guide as you walk to some of the most famous sights in the city while making as many gelato stops along the way as you can manage.

    Today's Highlights:

    • Take note of the Piazza della Signoria, home of the Uffizi Gallery and the world’s most famous nude man, Michelangelo’s David.
    • March your way across Ponte Vecchio, a medieval stone bridge with shops built along it (formerly butchers, now jewelers and souvenir shops).
    • Visit the final resting place of some of the most illustrious Italians such as Michelangelo, Galileo, and Machiavelli at the Basilica di Santa Croce.
    • Continue by bus to Montecatini, where the Tuscan countryside is dying to meet you.

    Day 6: Tour Medieval Tuscany

    When you’re in Tuscany, you visit Tuscan, medieval hill towns, you eat food, and you drink wine. We don’t make the rules, we just enforce ‘em. Today you’ll cross three towns off your list: Siena, San Gimignano, and Monteriggioni. Note: If you begin to experience a strong desire to stay in Tuscany forever, don’t panic—this is normal.

    Today's Highlights:

    • Join a local guide on a tour of Siena, where medieval architecture is king and strolling through town is also king.
    • Stop in at a cozy, local spot in Siena for a light lunch, followed by an opportunity to taste traditional pastries.
    • Visit a Tuscan wine estate and tour its wine cellars before tasting some wines for yourself.
    • Enjoy some time to explore the towns of San Gimignano and Monteriggioni on your own.

    Day 7: Explore the Italian Riviera & Cinque Terre

    Wake up and head to Cinque Terre (Italian for “Five Lands”). There you’ll find yourself looking at some of the most beautiful coastal scenery you’ve ever laid eyes on. Discover the colorful fishing villages that make for the best photo op of the entire trip. Scratch that. Best photos ever. Instagrammers, this is your moment.

    Today's Highlights:

    • Explore Cinque Terre and travel by train through the dazzling villages.
    • Stop in Manarola, the tranquil and unspoiled village that is too beautiful for its own good.
    • Catch some rays (of the sun variety) at the beach in Montesrosso, and relax after a long day of exploration.

    Day 8: Free Day in Montecatini

    Another day, another opportunity to eat, drink, and be merry in Tuscany. This time, you’re on your own to get out there and soak in as much wine—uh, we mean culture—as possible. But really, there’s so much to see and do, so get to seeing and doing already.

    Free Time Suggestions
    Corso Giacomo Matteotti: If you’re the kind of person who travels with an entirely empty rollerbag just so that you can fill it with souvenirs, then you’ll feel right at home on Montecatini’s premiere shopping street, famous for its luxury designer stores.

    Day 9: Travel to Perugia via Montalcino & Pienza

    What’s that? You want more wine and cheese tastings? Your wish is our command. On your way to Perugia, stop in Montalcino, Montepulciano, and Pienza for tastes of world-famous wines and Pecorino cheese.

    Today's Highlights:

    • Hop on the bus and make your way to three more Tuscan towns that are as much fun to visit as they are to say out loud.
    • Visit two wineries for a chance to try Brunello di Montalcino and Vino Nobile di Montepulciano, two red wines that you can name drop back home to impress your friends.
    • Chow down on some Pecorino cheese, a hard, salty and tangy cheese made from sheep’s milk, and decide if you’re #teamparmesan or #teampecorino.

    Day 10: Free Day in Perugia or Optional Trip to Assisi

    Perugia is incredibly quaint and incredibly-er authentic. Home to the University of Perugia, cozy cafes on every corner, an array of impressive ancient architecture, this town welcomes you with open arms. Take the day to explore on your own, or opt in for a day-trip to Assisi.

    Free Time Suggestions
    Sciri Tower: Get your steps in with an ascent to the top of Sciri Tower for some panoramic views of Perugia.

    Assisi and Umbrian Farm Lunch(extra cost)

    Assisi's striking medieval beauty makes it an Umbrian countryside must-see. See the Basilica of St. Francis with a local guide, then head to a farmhouse for lunch and a vineyard, winery, olive grove, and cattle farm tour.

    Why wait? Save money by booking this optional excursion before your trip departs.

    Day 11: Travel to Rome + Farewell Dinner

    Board your chariot (AKA bus) and head to the Eternal City: Rome. They say all roads lead to Rome, but you’ll quickly realize that all roads actually lead to restaurants and espresso. Explore centuries worth of culinary perfection, unbelievable architecture, and local fashion on your own today. And let it be said, Rome looks goooood for being 2,000 years old. (It must moisturize.) Embrace the culture and don’t be afraid to indulge during your last day in Italy.

    Today's Highlights:

    • Say ciao to Tuscany as you head to Rome on the final leg of your odyssey.
    • Enter the arena that is Rome—you are the gladiator, and pasta is your lion—and get your bearings for the day.

    **Farewell Dinner
    **Share some last laughs and revisit the best moments of the trip at this included farewell dinner with the group.

    Day 12: Fly Home

    Arrivederci, amici!
    Translation: Goodbye, friends. Your next destination awaits—home. Before you head to the airport, enjoy your last few moments together. Take one more group photo. Grab that final drink. (Fine, maybe a couple of drinks.) But this isn’t goodbye. It’s “See you later.” The only question is, where?

    – or –


    1. Double the fun
    A lot of our trips line up back to back! Give us a call—we can help you add another and save big while you're at it.

    2. Go ahead or stay behind
    Extending your trip is easy! During checkout, you'll have the option to fly to (or from) the gateway of your choice for an additional fee. We'll adjust your flights accordingly, but you'll be responsible to take care of your transportation, hotels, and other logistics outside of tour.

    Note: Depending on your desired gateways, additional fees may apply.

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