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Two Weeks Across Italy

Italy is hands down my most-asked-about country, and I can completely understand why. I have spent a total of 5 months in Italy and still have so much left to explore! This itinerary focuses on the most famous cities and the region of Tuscany;  I have a separate itinerary for the Dolomites because those mountains are too special to limit to just a few days. This itinerary is really a compilation of multiple trips I have taken to Italy, and I've also included recommendations from my time studying abroad there. With that said, you may have to cut certain places depending on how long you can travel, but I haven't been to a single place in Italy that I wouldn't recommend, so rest assured, you can't go wrong!

Day One: Rome

  • Depending on what time you land, you may want to grab a drink and take in the beautiful sites, 

    • Stop by or make reservations at Oro Bistrot (Rooftop Bar/ Restaurant)

  • Hit up the most iconic landmarks: (you can also try to see these early in the morning or late at night to try to escape the crowds)

    • Largo di Torre Argentina

    • ​Trevi Fountain

    • Pantheon

    • Piazza Navona

    • Stop by Mr. 100 Tiramisu

  • Relax at a Roman Spa: Aqua Madre​

  • Dinner/ Rest up for a full day tomorrow

Day Two: Rome

  • Mercato Trionfale

    • Food market that is open from 8:00 am-1:30 PM​

    • They offer food tours as well

  • Semi-Private Tour

    • Vatican City, Sistine Chapel, & St. Peter’s Basilica

  • Castel Sant’ Angelo (also a great sunset spot)

    • They have a small cafe on the rooftop

  • Dinner in Trastevere

    • Most of the restaurants in this neighborhood do not take reservations.​

Day Three: Rome- Florence

  • 10:30-1:00 PM Colosseum Private Tour:

    • Colosseum

    • Roman Forum

    • Palatine Hill

      • Absolutely purchase the private underground colosseum tour, which gives you access to the tunnels, dungeons, and cages that run below the arena

  • Lunch: AL42

  • Train to Florence (1.5 hour train ride)

    • Use the app Trenitalia to book your train tickets​

  • Walk around and take in the city ​(Florence)

    • Look for a wine window: Cantina dei Pucci 

    • Stop by the duomo at night

Day Four: Tuscany Day Trip

  • There are countless options in Tuscany. If you feel comfortable renting a car, I think it's well worth it to go off on your own and explore different towns and villages. You could even stay in Sienna or a Tuscan home instead of Florence if you wanted to take a break from larger cities. I think Florence is beautiful and well worth a visit, and it is a great home base if you'd rather have more options to explore in the evenings.
     

  • We Picked up our rental car right in Florence and made our way out of the city.

  • Stop One: Monteriggioni

  • Stop Two: San Gimigiano

    • We parked down the hill from the city and then walked up. There is no parking inside the city walls​

  • Stop Three: Castle Di Brolio

    • ​4:30 PM Wine Tasting

    • 6:00-7:00 PM Sunset Castle Tour, followed by Dinner

      • Wonderful Four-course meal and wine pairing​

      • You could also just do the tour/ dinner and skip the wine tasting to give you more time in the other towns.

  • Drive 1.2 hours back to Florence/ Drop off rental car​​

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Alternative day trips options: ​

Day Five: Florence

  • Duomo: Cathedral of Santa Maria del Fiore

    • 8:15am Tour of the duomo and the bell tower.

      • Note: There are countless, steep stairs so only book this if you are physically up for the task.

      • ​I highly recommend booking the earliest time slot to avoid congested stairs.

      • Don't skip the bell tower! It gives you a stunning view of the Duomo.​​

  • Piazza della Repubblica

  • Ponte Vecchio

  • Shopping: Florence is known for its leather market

  • Lunch

  • Piazzale Michelangelo (definitely go here for Sunset if you can)
     

  • If you choose to extend your time in Florence, other Tuscan villages/ cities you can add to your list include:

    • Pisa (About a 50 minute train ride from Florence)

    • Siena (About 1 hr 15 min. drive from Florence)

    • Volterra​ (About 1 hr 20 min. drive from Florence)

Day Six: Florence- Cinque Terre

  • Train about 2.5 hours from Florence to Manarola (or whichever city you choose to stay in)

    • Cinque Terre is 5 cities all right next to each other. I went to Cinque Terre while I was studying abroad in Italy back in 2014, but I've had many clients request to add this area to their itinerary. 

  • Check into hotel/ relax on the beach. There are countless beach options:​

    • Sand & Amenities beaches:

      • Spiaggia di Fegina (Monterosso): The only large sandy beach with paid beach clubs (umbrellas/loungers) and free public sections, plus restaurants nearby. 

      • Scoglio di Monterosso: A smaller, pebbly area in Monterosso Old Town, great for a quick dip near the iconic rock formation. 

    • Secluded & Nature Beaches:

      • Guvano Beach (Corniglia): A more rugged, pebbly beach accessed via a tunnel or steep hike, known for its natural beauty and relaxed (often clothing-optional) vibe. 

      • Canneto Beach (Riomaggiore): A beautiful, wild beach accessible only by boat or hike from Riomaggiore, featuring a waterfall. 

    • Picturesque Village Beaches:

      • Riomaggiore: A small, picturesque pebbly beach tucked below the colorful houses, great for a quick swim with stunning backdrops. 

      • Vernazza: A small, charming cove beach in the heart of the village, perfect for a dip after exploring. 

Day Seven & Eight: Cinque Terre

  • Hike Cinque Terre's famous coastline trails​.

    • Certain paths require a hiking pass.​

  • Lunch/ Explore some of the small towns​

    • You can easily access each town via the local train​

    • Some famous sites: 

      • In Riomaggiore starts the Via dell’Amore, Lover’s Lane, a wonderful path known for the romantic atmosphere and amazing landscapes. It is completely flat and leads to Manarola in less than 30 minutes.

      • In Manarola Enjoy an Aperitivo or a lunch at Nessun Dorma, a romantic bar overlooking Manarola.

        • You can download the Nessun Dorma app and digitally queue for your table 

  • Sunset Boat Tour

    • There are countless excursions that you can choose from.​

Day Nine: Cinque Terre- Lake Como

  • Enjoy a little more time in town/ at the beach before packing up and heading out to Lake Como.

  • Train about 3,5-4 hours to Lake Como (Como S. Giovanni)

    • We stayed in a Villa that was a short walk from Como City Center.​

  • Check into lodging/ stroll Como City Center​

Day Ten: Lake Como

  • We started with a slow morning- breakfast and lounge by our villa's pool

  • ​Private wooden boat tour- Lake Como villas

    • Our tour included a stop in Bellagio so we were able to explore the town for a little while​

    • 6 Hours

  • Dinner/ Walk around downtown Como​

    • Great shops and restaurants!​

Day Eleven: Lake Como

  • Brunch in downtown Como

  • Take the Como-Brunate Funicular up to Brunate

    • Enjoy the sights around town​

  • ​We walked around the shops in Como city center and grabbed a drink at one of the restaurants in one of the squares.
    ​

  • We were in Lake Como for a wedding and decided to take a day trip to Milan as well. 

    • Traveling to Milan from Lake Como by train was very easy and only took about 45 minutes​

    • If you choose to go, definitely reserve entry to the Milan Cathedral. Sadly, we did not do this in time, so we had to skip it.

Day Twelve: Lake Como-Venice

  • Train from Como to Venice (about 3 hours)

  • Take a private water-taxi from the train station to your hotel (try to stay near Piazza San Marco)

  • Walk around the city- take in the beautiful scenery!

    • ​St. Mark's Square

    • Doge's Palace

      • Buy tickets online to avoid the long line

      • 23 Euros

    • ​ ​St Mark's Belltower

      • Great views of the city​

      • 8 Euros

      • Early evening had shorter lines than the morning/ afternoon.

    • Dinner near the Rialto Bridge​​

      • There are several restaurants that line the canal.​
         

Day Thirteen: Venice

  • Cafe Breakfast

  • Gondola Ride 

    • It may be corny, but it's definitely worth it! The views of the city from the gondola are truly incredible.​

  • ​San Giorgio Maggiore

    • Beautiful Church with a bell tower on an island across from Venice. ​

  • Explore nearby islands

    • We only visited this one island before heading to Verona for a day trip. If you don't want to travel to another city, there are a ton of other islands to explore around Venice.

    • Burano and Murano are often recommended​

Day Fourteen: Fly Home

© 2024 by Mary Colombo

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