Italy itinerary 14 days Florence
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Italy Itinerary: 14 Days in Paradise

By Daisy Li

From the beautiful Venice on the lake to the historical center of Florence, from the picturesque islands of Cinque Terre to the holy Vatican city, most of the best sights in Italy can be experienced with in 2 weeks. Between stops at notable monuments, we still found time to wander each city endlessly.

Below is a list of tips & advice for the cities and towns I’d recommend anyone to visit if they’ve a short stay in the country. I will briefly go over my experience, things to be aware of, and the must-sees for each city. This Italy itinerary 14 days can definitely be adjusted according to your liking!

A Brief Overview of this Italy Itinerary 14 Days

Highlights of spending 2 days and 1 night in Venice:  

Doge’s Palace and Saint Mark’s Basilica in the evening to catch the sunset

Take a gondola or water taxi on the Grand Canal

Highlights of using Florence as a base for 5 days:

Visit the Cattedrale di Santa Maria del Fiore and the open air museum in Piazza Della Signoria

1-2 day hike in Cinque Terre

A morning stroll around Pisa

Highlights of staying in Rome for 4 Days:

Visit the historical Colosseum, Roman Forum, and Palatine Hill.
Strolls through the city center and other noted monuments
Leave a day for the Vatican City

Highlights and Recommendations for the remaining 3 Days

Best Time To Go To Italy

The best time to visit Italy is in the Spring or during the Fall season. Between May and June, and September and October, the weather in Italy will be picture perfect. Try to avoid school holidays and long weekends for cheaper prices and less tourism.

2 Days and a Night in Venice

Rio Priuli o de Santa Sofia (Venice)Didier Descouens
Experience: I arrived in Venice mid-noon in April. The temperature was a bit low and the breeze a bit chilly. A stunningly romantic city, the Venetian Lagoon did not fail to amaze. Crowded by people in some parts, there still remains a vast portion of streets and alleys untouched by tourist presence.

Make sure to confirm your hotel/Airbnb address before arriving! Although the location of my Airbnb was shown on Google Maps, it took me some time before figuring out that the address was wrong.

I ended up wandering the streets of Venice with my luggage. Not a fun experience after a flight :'(

Be Aware: Needless to say, the streets of Venice were confusing. On a map, the layout seems straightforward enough. It’s a tiny island with small streets here and there, resembling any other European city. The story is completely different when you are physically there. There were no less than a few thousand intersections and crisscrossing alleyways. Many streets were impossible to locate due to the numbering system (instead of having different street names, the houses are numbered in accordance with the districts).

Tips & Advice: It really isn’t an Italy itinerary without Venice! This beautiful town is best experienced by exploring the streets and small shops with a local. Stop by Doge’s Palace and Saint Mark’s Basilica in the evening to catch the sunset. Most spots in the township are easily accessible by foot, but do take a gondola or water taxi on the Grand Canal so you can enjoy the views of Venice from below.

Venice was extremely small and pricey. As such, a day in the town was enough. But to experience the romantic strolls at night, we decided to leave the following afternoon.

5 days in Florence

Use Florence as the base for Cinque Terre  (1-2 day) and Pisa (1 day)

Experience: Florence was around 2 hours from Venice. We took a BlablaCar for approximately EUR 15  per person, which was much cheaper and more convenient than Itali Rail. To be fair, Italy has a great rail system. But nothing beats people picking us up and dropping us off right at the door.

Although Florence was crowded with people and traffic, it remains one of my favorite destinations in Europe! Situated 10 minutes away from the spectacular Dome, our Airbnb was only EUR 19 for two beds!

The Cattedrale di Santa Maria del Fiore was breathtaking; the city magnificent, the open air museum in Piazza Della Signoria was extra charming with a saxophone soloist. There is so much to see here. From its beautiful architecture to its art and history, definitely, spend a few nights in this magical city. Piazzale Michelangelo has the best panorama views of the city!

Tips & Advice: To be honest, since the city is small, a day or two is enough to see everything. However, Florence is just charming enough and worth a few more days if you’ve 14 days in Italy! BlablaCar and Airbnb are extremely easy to use in Italy, and much more affordable and flexible in terms of booking. If you have a love for history, take a guided tour of Michelangelo’s David Guided with an art historian.

Italy Itinerary 14 Days: Cinque Terre

An Italy travel itinerary isn’t complete without this beautiful region.

Tips & Advice: Waking up at 6 am, we caught the earliest train at the Florence central station. Cinque Terre is famous for its 5 different villages and their colorful dwellings by the sea. Again, all the trains and associated timetables are available on Itali Rail .

The ticket for these villages as mentioned below are only sold at the station in La Spezia and the front desk of some hotels.

After arriving at Genoa train station (La Spezia), there is a separate train for these villages. The station provides a rather great explanation for what’s to come. They hand out little cards that detail the various trains times between each village, as well as the hiking trails between these little towns.

Experience: Unfortunately, only one of the hiking trails connecting the villages was open, but it was enough for the day. The hike was exhausting, lasting nearly 2 hours. We thought one day was enough for Cinque Terre. If you don’t want the hassle of catching the trains, join an all-inclusive day tour from Florence!

2 Week Italy Itinerary: Pisa

Experience: After returning to Florence for the night, we decided to stop by Pisa the next day. Instead of catching a train, we took a BlablaCar to Pisa. The ride was approximately 1.30 hrs and costed EUR 8 per person. On the way, the driver pointed out the Tuscany Vineyards, which was extremely beautiful.

Tips & Advice: If you’d like to catch the train, Regionale Veloce trains are the ones that serve this route. There are a total of 45 trains per weekday, with the first leaving Firenze Santa Maria Novella (SM Novella) at 00:40 am. It arrives at Pisa Centrale between 60-90 minutes, depending on the time of the day.  The ticket price ranges from US 10-12.

A day is definitely enough wandering the streets of Pisa, as the space containing all the famous architecture within the city is not too big. Participate in a guided tour of Pisa and its various monuments to better experience this gorgeous city.

Be Aware: A lot of people love bringing food for a picnic on the lawn of the Leaning Tower, but you will likely get hooted off by security.

4 Days in Rome

Italy itinerary 14 days Rome

Italy itinerary 14 days Rome at Night
Experience: We spent 4 days in Rome. Although the train from Florence was around EUR 50, we were able to find a BlablaCar for EUR15/ person. To be completely honest, Rome was a bit too touristy for my liking, although the architecture was absolutely breathtaking!

We spent a few days exploring the streets of Rome and ended up skipping a few tourist attractions due to the number of people. However, if you aren’t exactly keen on going inside the monuments, I found the experience of wandering around town during night-time was much better. There were barely any people and the lights were beautiful!

Tips and Advice: If you only have 14 days in Italy, 3 days was definitely enough for the main tourist attractions in Rome!

  • First Day: dedicate 3 hours to the Colosseum, Roman Forum, and Palatine Hill. This includes the wait in line and photo ops. A few hours should be spent walking around the city center, with stops at the Arch of Titus, Piazza Navona, Pantheon, Trevi Fountain and St. Peter’s Basilica. Don’t forget to stop by to get some Gelato and Pizza! This will be a long day, but everything is quite close together!
  • Second Day: Visit Trastevere, a quirky little neighbor in the area and explore the streets away from the major tourist attractions. I though Rome can be quite hectic if not planned wisely.
  • Third Day: Spend a day at the Vatican! The wait time for the Vatican can be up to an hour or more during the busier seasons

2 Week Italy Itinerary: The Remaining 3 Days

Truthfully, there is no way to experience all of Italy in 14 days. Nonetheless, the destinations mentioned in this Italy travel itinerary are the crown jewels of the country.

Without a doubt, Italy is so much more than these few cities. There is Milan, one of the fashion capitals of the world. (Visit before or after Venice since it is located in North Italy). Bologna is yet another great stop located between Florence and Rome. Down south, you have the beautiful waters of the Mediterranean. Visit Naples or the breathtaking Sicily.

This is definitely a very fast-pace and tiring agenda for those who are physically able. However, if you are on a tight schedule yet don’t want to miss any of the spectacular sights, (like myself), this might do!

Total Cost

We spent around CAD 500 for the two of us. This was a pretty expensive trip compared to my usual backpacking journys. But since we opt for nicer Airbnb instead of Couchsurfing, it was quite worth it!

CAD 300 was spent on Airbnb. Aside from the cheaper stay in Florence, Venice and Rome were pretty pricey. The rest were on transportation throughout the country. Trains in Italy were expensive. I didn’t really notice it until going to Cinque Terre due to the lack of BlablaCars in that region. I believe we ended up spending CAD 100 just for the various trains throughout the day.

Nevertheless, this was such a great experience and definitely worth the trip! If you ‘ve any questions about this Italy itinerary 14 days, feel free to email me!

Happy Travels xx

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