Ultimate Break company logo
Ultimate Italy

Ultimate Italy

17 days, 6 cities120
See dates and prices

From $2969 without flightsPayments as low as $96

Trip Type:
Activity Level:

Why go?

The *chef’s kiss* Italian experience. Blissfully lose yourself among the historic churches and narrow winding streets of Venice. Explore the stunningly colorful villages of Cinque Terre. Discover the incredible history of Rome and Pompeii. Oh, and we heard the food’s decent, too.

Picture yourself

  • Riding in a gondola through the canals of Venice

  • Eating the cacio e pepe you typically dream about

  • Snapping #nofilter photos at Cinque Terre

  • Looking up at Mt. Vesuvius from the city it made famous, Pompeii

What you'll get

  • Round-trip flights & airport transfers (or book 'em yourself)

  • 1 overnight ferry

  • 14 nights in handpicked accommodations

  • 15 breakfasts

  • 2 dinners

  • Expert Tour Director

  • 24/7 Support

  • 7 insider city tours with a local guide

Map for the Ultimate Italy tour
Full trip itinerary


  • Day 1: Overnight Flight

    Board your overnight flight, bound for Italy! Fresh gelato and homemade pasta will soon be yours. So, so soon.

  • Day 2: Arrive in Venice + Welcome Dinner

    Welcome to the Venice Region! While you'll be staying on the mainland, the heart of Venice is a quick bus ride away. Situated on 118 islands, intersected by 175 canals and connected by more than 400 bridges, this city has had more praise showered upon it from travelers, writers and artists than any other city in the world.

    In the evening, enjoy a Welcome Dinner of local cuisine and drinks with fellow travelers at an authentic local spot. Afterwards, you’re free to take the party elsewhere!

    Today's highlights:

    • Meet an EF representative at the airport.
    • Transfer to your accommodations and check in.
    • Receive the latest schedule from your Tour Director.
    • Meet the other travelers as they arrive.
    • Meet your Tour Director for a guided tour of some top sights around Venice.
  • Day 3: Tour Venice

    Get ready to see Venice through the eyes of a local Italian. Your guide will show you canals, an extraordinary basilica, and a staircase shaped like a snail. You definitely haven’t had enough pasta yet. Eat more pasta.

    Today's highlights:

    • Travel from mainland Venice to the island, catching sight of St. Mark's Basilica, plenty of gondolas, and the spectacular Venetian skyline.
    • See several historic churches and lose yourself in the narrow streets of Venice.
    • Follow the winding Grand Canal through the heart of Venice
    • Play Marco polo from across the Rialto Bridge, the oldest bridge in the city that connects San Marco and San Polo.

    Free time suggestions

    Book Worm: Check out Acqua Alta Library, a hidden bookstore where the books are piled from floor to ceiling, and kittens run around just waiting for some company.
    300 Years Young: Opened in 1720, Caffè Florian is the oldest café in the world. And while the venue may be old, their beliefs have always been ahead of their time. They were the only café to serve women during the 18th century. Nicely done, Florian.
    Go for Gondola: Make your dreams come true by floating down the Venetian canals aboard traditional gondolas.

  • Day 4: Travel to Milan via Verona

    Say goodbye to Venice; you’re on to Milan, the design, fashion, and commerce center of Italy. On your way, stop in Verona, the setting for three of William Shakespeare’s plays. Visit Juliet’s balcony where you can harness you inner Romeo by saying, “But, soft! What light through yonder window breaks?”

    Today's highlights:

    • Travel by bus to Milan with a pit stop in Verona.
    • Pay a visit to Juliet’s famous balcony and get in touch with your inner romantic.
    • Arrive in Milan and take an introductory walk of the area with your Tour Director.
    • Take the evening by storm; Milan is a vibrant, fast-paced city that certainly won't slow down at night. Will you?

    Free time suggestions

    Mall Rats: One of the world’s oldest malls, the Galleria Vittorio Emanuele II (who knew malls existed in 1877?), is the place to go if you want to window shop for Gucci or Louis Vuitton. Beware: the prices are as high as the vaulted ceilings. But the vaulted ceilings are beautiful.
    Bar None: Head out on the town to any one of the dozens of bars throughout the city. And if you’re feeling even more adventurous, there are plenty of dance clubs calling your name.

  • Day 5: Free Day in Milan or Optional Day in Lake Como: Villa Carlotta & Bellagio by Boat

    Cruise Lake Como on a full-day excursion or enjoy a full free day in Milan to explore on your own. Either way, you're about to have a great day.

    Today's highlights:

    • Wake up and seize the day; you've got Milan at your fingertips.
    • Explore the impressive gothic cathedral that offers stunning views of the city.
    • Spend the day at Lake Como (if you choose), daydreaming about villa life and spotting celebrity homes.

    Free time suggestions

    Stairway to Heaven: Visit Milan’s impressive gothic cathedral, as stunning on the outside as it is on the inside. Climb the stairs (or take the elevator) to the top for sweeping views of the city’s skyline.
    Gol!!!: If you’re a soccer fan, take some time to visit the San Siro Stadium and museum, home to AC Milan, one of the top soccer clubs in Italy.
    Drinks After Work: Like many people, the Milanese like to take the edge off after a day at work. Do as the Italians do, and find a café for a drink (aperetivo) and snack.

    Day in Lake Como: Villa Carlotta & Bellagio by Boat (extra cost)

    Cruise serene Lake Como, where views of the Alps, villas and small medieval towns line the shore. Then, explore two of Italy's most beautiful celeb hotspots: Como and Bellagio.

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

  • Day 6: Travel to Florence via Cinque Terre

    Board your private coach for Florence via Cinque Terre, the five colorful fishing villages that will 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.
    • Arrive in Florence in the evening, settle in, and take an introductory walk with your Tour Director.
  • Day 7: Tour Florence

    You’ve got a full day in Florence, the compact capital of the Tuscany region known for its famous Renaissance artwork. Throw on some comfortable shoes and join a local guide for a walking tour of the city. By the end of it, you’ll be looking up how to live in Italy forever.

    *Note: There is no included entry to the Duomo during the guided sightseeing on this day, but you will have free time to return if you so choose.

    Today's highlights:

    • Cross the Ponte Vecchio, the oldest bridge in Florence, home to many of Florence’s jewelers and art merchants. Ready to get some bling?
    • Stroll the Piazza della Signoria, home to Florence’s seat of power, the Palazzo Vecchio, as well as several intricate sculptures.
    • Visit the Duomo Cathedral. Return during your free time and challenge yourself to climb the 463 steps to the top for stunning views of the city.

    Free time suggestions

    Get Some Fresh Air: Loggia dei Lanzi is an open air sculpture museum, with a number of Renaissance statues. It’s beautiful, it’s in the open, and it’s free.
    Leather-Bound Books: Florence is known for its plethora of leather goods, from belts and jewelry to purses and wallets. Maybe you can finally buy that leather jacket you’ve always wanted but have been too embarrassed to buy.

  • Day 8: Travel to Rome via Orvieto

    Travel to Rome via Orvieto
    Travel to Rome via Orvieto. Goodbye, Florence. Hello, Rome, Italy’s capital city that is bursting at the seams with energy. Locals fill the streets, day and night, usually doing something that involves eating or drinking. And how can you blame them when pasta, pizza, gelato, coffee, and wine are everywhere you look? Rome is all big city/ancient ruins, served with a side of spaghetti.

    Today's highlights:

    • Board your private coach, bound for Rome.
    • Stop in Orvieto, a quaint Italian hill town that’s as fun to visit as it is to say in an Italian accent.
    • Marvel at the artistry of the facade of Orvieto’s stunning cathedral, built in 1290 (no, that’s not a typo—it’s really that old.)
    • Arrive in Rome, surrounded by art, ruins, and 2.9 million people
    • Take a tour of the surrounding area with your Tour Director, stopping by some famous attractions, and more than few gelato shops.
  • Day 9: Tour Rome

    They say all roads lead to Rome, but once you’re there you quickly realize that all roads actually lead to restaurants. Take the morning to satisfy your cravings and sip some espresso, then experience everything ancient Rome has to offer with a local guide.

    Today's highlights:

    • Tour the city with a local guide who will show you why Rome is one of the most legendary cities in Europe.
    • Experience the heart of ancient Rome with a visit to the Forum, once a hub of activity for the city.
    • See the ruins of several Roman temples, including the Temple of the Vestal Virgins.
  • Day 10: Tour the Vatican City

    Stroll Vatican City, home of the Pope and headquarters of the Roman Catholic Church. Prepare for crowds, but for good reason. This is an opportunity to visit the smallest country in the world, plus catch a glimpse of the most interesting ceiling you’ve ever seen.

    Today's highlights:

    • Get an in-depth look into Papal history and politics with an expert guide.
    • Cross another country of your list (Vatican City is an independent nation).
    • Look up (like, straight up) at the frescos of the Sistine Chapel, Michelangelo’s greatest work.
    • Visit the Vatican Museum, one of the largest, most renowned art exhibits in the world.

    Free time suggestions

    Trevi Fountain: Rumor has it, if turn your back to the Trevi Fountain and toss a coin over your shoulder, it guarantees you’ll return to the Eternal City. Throw in a second coin, and you’ll not only come back, but also find love. (Significant other not guaranteed by EF Ultimate Break.)
    Shopping on Vide del Corso: Walk down the longest pedestrian street in the city for some prime shopping. Populated by both locals and tourists, there’s room for everyone on the narrow store-filled street.

  • Day 11: Travel to the Naples Region via Pompeii

    Travel to the Naples Region via Pompeii
    As you make your way to the Naples Region, join a local guide for a walking tour of the ancient city of Pompeii, which stands frozen in time after Mt. Vesuvius erupted in 79 AD, completely destroying the town.

    Today's highlights:

    • Travel back to imperial Roman times and learn about Pompeii, the city covered in volcanic ash.
    • Look up at Mt. Vesuvius, the deadly volcano that annihilated this city almost 2,000 years ago.
    • Experience the buildings, artifacts and even people that have been extremely well preserved over the years.
  • Day 12: Enjoy a Free Day in Naples Region + Optional Capri Cruisin

    The day is yours to do as you wish. Or join your Tour Director for an excursion to Capri. You haven’t lived lavishly until you’ve cruised around the island of Capri. You'll leave the big city life behind you, and enjoy more of that classic Italian coastal beauty. And if you're wondering, yes, this is what heaven looks like.

    Today's highlights:

    • Get lost in the Naples Region during your free time.
    • Spend a full day on the Isle of Capri for an afternoon cruise and tour with a local guide during an optional excursion. (Life of luxury much?)
    • Enjoy the thing that Naples is known for, that bready, cheesy, tomato sauce topped stuff we call pizza.

    Capri Cruisin' (extra cost)

    Ferry across the Bay of Naples then around the Isle of Capri, gawking at the incredible Arco Naturale and the famous Faraglioni rocks. Then travel by funicular railway to the ancient mountaintop island resort.

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

  • Day 13: Free Day in Naples + Board Night Ferry to Palermo

    Lucky you—a full day to enjoy more of Naples before heading to Palermo.

    Today's highlights:

    • Use your free time in the Naples Region to do as you wish.
    • Grab lunch, veg out on the beach, and bask in that sweet, sweet Vitamin D.
    • Head back to the ferry port in Naples and board your overnight ferry to Palermo, Sicily.
  • Day 14: Travel to Catania Region

    Hop off the boat in Palermo, stop at a beach in Cefalù, and then it's on to the lively region of Catania.

    Today's highlights:

    • Get off the ferry and kiss the ground (that's what they do in the movies, right?)
    • Grab lunch, peek into tiny shops, and catch some rays at one of Sicily's finest beaches in the town of Cefalù.
    • Continue on to Catania region, and relax at an outdoor café as day turns to night.
    • Make the most of your night; go on the hunt for more fine, Italian cuisine and wine on wine on wine.
  • Day 15: Free Day + Optional Mt. Etna Excursion

    The day is yours to explore. Enjoy your free time or take an excursion to the apex of Mt. Etna, a massive active volcano on the eastern coast of Sicily. Don’t forget to eat all the last minute pasta and gelato you can.

    Today's highlights:

    • Continue exploring the noisy, yet always charming region of Catania.
    • Try some pasta alla Norma, yet another delicious pasta dish that originated here in Catania. (It should be noted that this is your last day to enjoy Italian pasta.)
    • Find your way to the beach to catch some last minute Italian rays.
    • Get in some mountain time by joining in on the Mt. Etna optional excursion.

    Mt Etna: Volcanos & Wine Tasting (extra cost)

    See and explore the craters of Europe's tallest active volcano, then relax with some Sicilian wine.

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

  • Day 16: Explore Taormina + Beach Day

    Today you’ll explore Taormina, the posh town literally built on the side of a mountain. Once you stand in the ancient amphitheater, overlooking the Mediterranean Sea, you’ll understand why more people are flocking here every year.

    Farewell Dinner
    Share some last laughs (and maybe shed a few tears) at an included farewell dinner with the group.

    Today's highlights:

    • Bask in the spectacular views of Mt. Etna, the tallest active volcano in Europe.
    • Explore the 7th-century Taormina Greek Theater, which is still in use today. (Bob Dylan once performed here.)
    • Take in the Baroque architecture and quaint, pedestrian-friendly cobblestone streets.
    • Return to the Catania region in the evening for another night doing whatever you please.
  • Day 17: 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?



    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.


Overall rating: 4.6 out of 5
Based on 120 authentic traveler reviews
  • Don’t think, just do it

      Meredith, traveled May 2024

    This was a once in a lifetime trip that I could not have planned better myself. We saw over 20 cities in the 15 full days we had and it was mind-blowing. It’s very fast-paced but you also get just enough free-time. Libera did an amazing job guiding us. She had great recommendations for restaurants, things to do, things to eat, and what NOT to do/eat of cours... See more


      Victor, traveled Apr. 2024

    If you’re wondering whether or not you should splurge for this trip… DO IT! You get to go everywhere and explore so much from Venice all the way down to Sicily. Our tour director, Simone, gave us so much laughs, knowledge, and memories from the very first day. The EF and Simone’s excursions made the trip so much fun! So again, if you’re wondering whether or ... See more

  • Trip of a lifetime!

      Abrielle, traveled Sep. 2023

    A trip of a lifetime- I truly couldn’t have dreamed of a better experience! Simone was our guide and absolutely brought our trip/ travel experience from incredible, to outstanding! Best trip ever! I’d repeat it all in a heartbeat if I could.

  • Gorgeous Country, Amazing Director

      Samuel, traveled Sep. 2023

    Beautiful trip! If anyone gets a chance to go to Italy try to book Simone as the tour director, he was incredible.

  • 1
  • 2
  • 3
  • 4

Select your date

  • No Flights Included 
  • Albany, NY 
  • Albuquerque, NM 
  • Amarillo, TX 
  • Anchorage, AK 
  • Atlanta, GA 
  • Austin, TX 
  • Baton Rouge, LA 
  • Billings, MT 
  • Birmingham, AL 
  • Bismarck, ND 
  • Boise, ID 
  • Boston, MA 
  • Bozeman, MT 
  • Bradley, CT 
  • Bristol, TN 
  • Buffalo, NY 
  • Calgary 
  • Cedar Rapids, IA 
  • Charleston, SC 
  • Charleston, WV 
  • Charlotte, NC 
  • Chattanooga, TN 
  • Chicago, IL 
  • Cincinnati, OH 
  • Cleveland, OH 
  • Colorado Springs, CO 
  • Columbia, SC 
  • Columbus, OH 
  • Corpus Christi, TX 
  • Dallas, TX 
  • Dayton, OH 
  • Denver, CO 
  • Des Moines, IA 
  • Detroit, MI 
  • Edmonton 
  • El Paso, TX 
  • Fairbanks, AK 
  • Fayetteville, AR 
  • Fresno, CA 
  • Grand Rapids, MI 
  • Great Falls, MT 
  • Green Bay, WI 
  • Greensboro, NC 
  • Greenville, SC 
  • Helena, MT 
  • Honolulu, HI 
  • Houston, TX 
  • Huntsville, AL 
  • Indianapolis, IN 
  • Jackson, MS 
  • Jacksonville, FL 
  • Kansas City, MO 
  • Knoxville, TN 
  • Las Vegas, NV 
  • Lexington, KY 
  • Little Rock, AR 
  • Los Angeles, CA 
  • Louisville, KY 
  • Lubbock, TX 
  • Madison, WI 
  • Memphis, TN 
  • Miami (MIA, FLL) 
  • Midland, TX 
  • Milwaukee, WI 
  • Minneapolis, MN 
  • Missoula, MT 
  • Mobile, AL 
  • Montreal 
  • Nashville, TN 
  • New Orleans, LA 
  • New York/New Jersey (EWR, LGA, JFK) 
  • Norfolk, VA 
  • Oklahoma City, OK 
  • Omaha, NE 
  • Orlando, FL 
  • Pensacola, FL 
  • Philadelphia, PA 
  • Phoenix, AZ 
  • Pittsburgh, PA 
  • Portland, ME 
  • Portland, OR 
  • Raleigh Durham, NC 
  • Rapid City, SD 
  • Reno, NV 
  • Richmond, VA 
  • Roanoke, VA 
  • Rochester, NY 
  • Saginaw, MI 
  • Salt Lake City, UT 
  • San Antonio, TX 
  • San Diego, CA 
  • San Francisco, CA 
  • San Jose, CA 
  • San Juan, PR 
  • Savannah, GA 
  • Sacramento, CA 
  • Seattle, WA 
  • Shreveport, LA 
  • Sioux Falls, SD 
  • South Burlington, VT 
  • Spokane, WA 
  • Springfield, MO 
  • St.Louis, MO 
  • Syracuse, NY 
  • Tampa, FL 
  • Toronto 
  • Traverse City, MI 
  • Tucson, AZ 
  • Tulsa, OK 
  • Vancouver 
  • Washington DC (BWI, IAD, DCA) 
  • Wichita, KS 
  • Wilmington, NC 
  • Winnipeg, MB 
Travel year:
Back to top