Two Week Italy Itinerary

This Italy itinerary is the recap of our fantastic 2 week Italian vacation this past September. While planning, we struggled a little with nailing down the details. Knowing that we couldn’t go for more than 2 weeks, with so many potential stops, we did consider a number of options. Looking back, I think that this itinerary offers a good balances of seeing and experiencing as much as possible without having to sacrifice too much time to traveling from city to city.

Having logged over 172 km (107miles) by foot during our trip, I wouldn’t say that it was a very relaxing trip, but we did get to experience and see so much. One thing is for sure, Italy now has a special place in our hearts and would go back in a hearbeat.

Days 1 to 4: Rome

Our flight arrived in Rome around noon local time. After deplaning, it was fairly quick to go through passport control, pick up our luggage and hop in a taxi to our hotel.

While in Rome, we stayed at the St. Regis which was definitely as splurge (thank you Bonvoy points!) but worth it. It’s a wonderful hotel with exceptional service.

Some of the Rome highlights include a tour of the Vatican, a Colosseum tour and wandering the streets of Trastevere.

For more details about our 3 days in Rome, click here.

Days 4 to 6: Venice

On day 4, we hopped on a morning train to Venice. In a little under 4 hours we were there.

Venice is enchanting and much more beautiful than I had imagined. It was very busy with both the Historical Regatta (Regata Storica) and the Venice Film Festival taking place.

While there, we did a private walking tour, which was a great way to see and learn more about the city’s history. It was also a great way to get great food recommendations from a local.

We opted to stay at the JW Marriott Venice. This was the perfect choice since it’s located on a private island a 20 minute boat ride away from the crowds.

For more details on how we spent our 2 days in Venice, click here.

Days 6 to 8: Bologna

Day 6 brought on a short train ride from Venice to Bologna. Before deciding to go to Bologna, we hadn’t done much research so weren’t quite sure what to expect except for good food. And, it sure didn’t disappoint!

This is where we definitely save a bit on accommodations and stayed at the AC Hotel in Bologna. It was a short walk away from the main attractions, but a very reasonably priced option.

While there we took a walking food tour in the city and an e-bike tour in the country side. Both were fantastic. But the highlight of Bologna was the food. There is so much to say, but I’ll save it for a separate post.

Days 8 to 10: Cinque Terre

While planning the trip, for me a must do was a visit to Cinque Terre. I had seen many pictures of its colorful towns and knew I couldn’t be in Italy and not see it for myself. So, on day 8 we traveled to Monterosso, Cinque Terre. It didn’t disappoint.

There aren’t a lot of hotels in the area so we opted to stay at an AirB&B for the two nights. It was very charming and quite comfortable and allowed us to get a few loads of laundry done.

Most of the trip went as plan, but this is where our plans didn’t quite pan out. And, being flexible and not really having any firm expectations really helped. The one day that we had to visit all the the 5 towns of Cinque Terre, there was a train strike. So, we made the best of it and hiked to the next town, Vernazza. We did miss out on the other 3 towns but that just gives us a reason to go back.

For more details about our 2 days in Cinque Terre, click here.

Days 10 to 15: Florence

Florence was the final stop on our Italian tour and also our longest. We were able to spend 5 days exploring what this great city has to offer. Some of the Florence highlights include the pizza and gelato making course, the past making course, the Tuscan biking tour and the shopping.

While in Florence, we stayed at the Sina Villa Medici. At the time, the city was quite busy with tourists and accommodations quite expensive.

For more details about how we spent our 5 days in Florence, click here.

Finally, stay tuned for more content! We have a lot more to say about this trip, this Italy Itinerary only scratches the surface.

• Two Days in Bologna
• Three Days in Rome
• Visiting Cinque Terre
• Five Days in Florence
• Our Top Italy Travel Mistakes

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