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Gladiators, Gondolas & Gold on The Tracks: Your 2 Week Italy Itinerary

two week itinerary italy tips and plan
Photo by Unsplash

Two weeks is the perfect amount of time to spend on holiday, especially if you are travelling to a very different time zone. One week just isn’t enough time to get rid of your jet lag, and with three weeks you’ll probably start missing your own bed. So congratulations on choosing the perfect amount of time to spend on your vacation to Italy!



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This article lays out a two-week itinerary for your trip to Italy, so you can make sure you hit all of the important stops, but don’t feel too drained at the end of each day.

Day 1 – 3 Arrive in Rome

On day one you will step out of the airport into the rejuvenating Mediterranean sunshine, feeling a mix of extreme exhaustion and wonder at your new surroundings.

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You don’t need to make any big plans today, but it is important not to go to sleep as soon as you get to your lodgings — instead you should try to stay up until a natural Italian bedtime (you can make it a little earlier, as Italians have a habit of staying up into the early morning hours).

Tourists inside the Roman Colosseum, Rome, Italy
Here are some things you can do while you walk around this afternoon:

    • Spanish Steps: Possibly the world’s most famous staircase. Great for people-watching and obligatory Instagram photos.

      Trevi Fountain
      : After the Spanish Steps, walk to Trevi Fountain. This is another crowded tourist area, but you must go there to throw a coin in the fountain, ensuring that one day you will return to Rome.

      Pantheon
      : With fewer coins in your pockets to weigh you down, head to the Pantheon, one of the best preserved examples of the astounding ability of the Roman architects from 120 AD.




      Piazza Navona
      : To end your afternoon, head to Piazza Navona, largely agreed to be the city’s most beautiful square with three fountains and breathtaking baroque architecture.
  • Now that you’ve had a good night’s rest, it’s time to start your second day early and really dive into Rome’s history.

      The Colosseum: Transport yourself back in time with a visit to the largest amphitheater in the world. The Colosseum is one of the New 7 Wonders of the World and was constructed almost 2000 years ago, with completion in 80 AD. You should book your tickets in advance to avoid long lines. It will take you about an hour to visit the colosseum, unless you take a premium tour which will make your visit about 3 hours.
      The Roman Forum: The Roman Forum is the heart of ancient Rome. Your ticket to the Colosseum most likely will include entry to the Forum as well. You can also walk up to Palatine Hill for spectacular views over the Forum and the city. Make sure to read up on the Forum’s secrets so you can really feel like you’ve gone back in time.
      Lunch: Time to enjoy some of the best cuisine in the world. Instead of sitting down at the first restaurant you find, try to always go even just one block off the beaten path, you’ll find that quality and authenticity rises exponentially.
      Borghese Art Gallery: Spend the afternoon in the Borghese Art Gallery where you can enjoy not just spectacular works by Raphael, Caravaggio and Bernini, but also some refreshing air conditioning.

    You can take the rest of the afternoon to wander around like a local, or visit every church you come across, because whether you are religious or not, they are all breathtaking on the inside. Afterwards have dinner in Trastevere. This charming neighborhood offers a plethora of hole-in-the-wall dining opportunities.

      Vatican City: On your third day, spend all morning in Vatican City, visiting the Sistine Chapel and enjoying world class art and architecture.
      Shopping: Spend the afternoon hitting up Via del Corso, one of the city’s longest streets, and outfit yourself to look like a native Roman.

    Day 4-7 — Florence

    Rail holidays in Italy provide the most convenient way to get around during your stay. Take the train from Rome to Florence and spend a bit over an hour in a comfortable chair watching the beautiful countryside go by.
    Palazzo Vecchio, Florence, Italy
    Take advantage of this downtime to reflect about the highlights of your time in Rome, because once you get to Florence, you’re in for a whole other round of awe-inspiring sights. Here are just some of the things that you will want to make sure you do during your three days in Florence:

      Duomo: Head to the heart of Florence to visit the Duomo, Cathedral of Santa Maria del Fiore. You will need to purchase the OPA Pass, a ticket that includes the dome, the Baptistery, Giotto’s Bell Tower, the Cathedral, the Crypt and the Opera Duomo Museum. This will take up the whole morning and potentially the afternoon as well.
      Piazza della Signoria: Spend your second day in the heart of Florence’s old town. You can visit the free open-air sculpture gallery and see the medieval Palazzo Vecchio.
      Pont Vecchio: This charming bridge was built over the Arno river in 1345, and is the only bridge that survived the WWII bombing of the city. Shops selling gold and silver jewellery line the bridge if you want to pick up some Italian bling.
      Mercato Centrale: The Mercato Centrale is the perfect place to visit if you’re looking to do some more shopping. You can find genuine leather goods, tasteful souvenirs, antiques and authentic food.
      Day trip to Tuscany: Enjoy wine and ridiculously delicious Tuscan food, accompanied by rolling countryside and charming villages. There are plenty of tours you can choose from to find the right one for you.




    Day 8-9 — Cinque Terre

    Italy itinerary, Cinque Terre
    Photo by Bjorn Snelders on Unsplash

    On day eight, take the train from Florence to the Cinque Terre where you will arrive in La Spezia. From La Spezia you can take a local train to one of the five towns of the Cinque Terre. Arrive in your town, walk around and enjoy dinner and breathtaking sunset views.
    On day nine tour the five towns by train, bus, boat or foot. Hiking trails and trains connect each town, so you can do a combination if you want some exercise but don’t want to end up exhausted. Just make sure you bring some good hiking boots. Or maybe you’re looking for something a bit different? Why not turn your tour into a five-town pub crawl



    Day 10-12 — Milan

    Take an early morning train from La Spezia to Milan. Spend your two days visiting sites such as:

    • Duomo of Milan: The largest gothic cathedral in the world.

      Sforza Castle
      : Milan’s Castle is home to a plethora of art museums, one of which contains Michelangelo’s last sculpture. The castle itself is quite enchanting for those obsessed with Medieval history.

      La Scala Opera House
      : If you can swing it, make sure to see an authentic Italian opera. You will never forget it for the rest of your life.

      Day Trip to Lake Como
      : You can catch the train from Milan and travel just 45 minutes to Lake Como. Take a ferry and to some star-watching while you pass by George Clooney’s house. Then head to Bellagio where you can get lost in cobblestone allies and charming cafes.
  • Day 13-15 — Venice

    2 week italy itinerary venice
    Photo by Tom Podmore on Unsplash
    Take the train from Milan to Venice and end your Roman holiday in Italy’s sinking city.
    These are your last days in Italy, so don’t be afraid to take advantage of every opportunity, no matter how touristy it may be. Things that you absolutely shouldn’t skip include:

    Doges Palace tour
    St. Mark’s Basilica
    Gondola ride around the canals

    After your two weeks in Italy, you will probably be a bit sad to leave and already thinking about what you want to see during your next visit (let’s hope you remembered to throw a coin in Trevi Fountain).
    You’ve visited a lot during this tour, but Italy is home to a wealth of information, art, culture and history and you might want to consider visiting places you missed during this visit, such as Pisa, Verona or Bologna.



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