2 Weeks in Italy : Travel Advice and Itinerary

About a year ago my fiancé and I got to go on our dream trip to Italy. We had been talking about going on a trip like this for years, so it was definitely a great feeling to have everything booked and know that it was finally happening. This was the most research we have ever put into a trip. To be fair, that was our “biggest” trip to date so it actually required research. It took a little bit of time but was well worth it in the end.  Anyway, we were super excited about this trip. I will have to say, my fiancé did the bigger chunk of the research, so I better give him the credit that he deserves.

So, this is going to be my attempt to write out the layout of how to spend 2 weeks in Italy. I will talk about what went well and what didn’t go so well. So grab some coffee and a snack because this is going to be a long post. Also, coming soon – I will be breaking it down to city by city guides as well, so this is just going to be my comprehensive overview of how to spend 2 weeks in this beautiful country. This is more of the logistics aka getting around the country, suggestions of how to prepare for a trip like this, etc.

Booking the Flight

We booked our flight about 7 months ahead of time , which may have been a tad bit excessive and I definitely don’t think it’s necessary to book that far out. We are both graduate school student so we had to take advantage of winter break – that’s pretty much the only reason we booked it so early. I think booking 5 – 6 months out is the perfect time because it gives you plenty of time to plan but it also prevents you from buying overpriced tickets. We were researching prices for weeks ahead of time (and making sure to erase search histories each time as we saw that airlines can track that and raise prices based on demand).

We did find via research that Milan was the cheapest airport in Italy to fly into. So we decided to start our trip in Milan (which is located in the northern part of the country) and make our way down to the Amalfi Coast which was our southern-most stop. On our last full day we took a 7 hour train from Naples to Milan and flew out the next morning out of the same airport.

We did try to choose tickets with which we would end up in Milan early in the morning so that we could sleep the whole plane ride and then be ready to explore as soon as we got off the plane. This ended up working out very well and I do recommend either flying in early in the morning if you are someone that can sleep on the plane. If not, I would recommend flying in at night, so that you could get a good night’s sleep before exploring the gorgeous city of Milan.

Our Itinerary

So this is how our 2 week break down (city wise) looked:

Day 1 – Milan

Days 2-4 – Venice

Days 5-6 – Florence (+Cinque Terre)

Day 7 – Pisa

Day 7.5 – 10 – Rome

Days 11-13 – Amalfi Coast (Praiano)

Day 14 – Train ride back to Milan

What we did right: Flying into Milan. Leaving 3 days for Venice. Saving Amalfi Coast for the end of the trip

What we did wrong: Spending half a day in Pisa (you only need a few hours). Only leaving 3.5 days for Rome (there is never going to be enough time in Rome).


We were able to get from one city to the next via train. TrenItalia to be exact. We booked everything online ahead of time and I would highly recommend that as 1) it’s cheaper and 2) that way you have a set schedule and know when you are supposed to be at the train station. The trains generally ran right on schedule and the only problem we had was not realizing that there are assigned seats and not always being able to sit next to each other for long rides wasn’t the best. The language barrier made it a bit difficult to switch people seats but overall it wasn’t too bad. The trains themselves are clean and comfortable. If you like flexibility in your schedule you can purchase tickets there at the station but look out for people trying to sell you fake tickets. They are good at spotting tourists and will try sell you tickets that won’t work. We were approached in Rome trying to sell us “discount tickets” but luckily we already had our tickets and this got them to stop trying to sell them.

If we had to get to the other part of the city (in Rome to be exact because it’s a fairly large city) we used the subway. It was very affordable and the system was pretty easy to navigate and understand. I would recommend planning ahead of time what day you will be doing something far from where you are staying and take the subway in and chose other locations nearby so that you aren’t constantly buying subway passes. If you are staying in Old or New Rome, you will most likely have to take the subway to the Vatican if that’s in your plans. Milan, Florence and Pisa are all very walkable if you are in good (or at least okay) shape. Venice is an amazing city that is fun to walk around and get lost in but it can also be fun to take the water taxi/bus which is 7 euros a ride and can take you around the city much faster.


We booked 4 guided tours for the trip and spontaneously bought one right at the site. We had one walking tour of Venice that included a boat tour that was excellent and I would highly recommend it. The boat tour was personally my favorite part (and if you don’t want to pay $100 for a gondola ride, this would be an alternative). We had the walking tour in the morning, a several hour break for lunch and a meeting spot for the boat tour which was in the afternoon. I do wish the gap between the boat tour and the walking tour was a lot shorter because we had several hours after lunch that we would have rather used for the boat tour so we could plan other plans for later in the day. We booked a full day Cinque Terre tour from Viator (you can find it here) which I highly recommend which left from Florence. The tour was a full day tour and included a lot of hiking. I will talk more about that during my Florence and Cinque Terre post. We booked a tour for the Tower of Pisa that gave us skip the line access along with access to the very top of the tower. We also were able to visit the Duomo next to the tower for free because of those tickets and that Duomo was a lot more impressive than expected. We also booked a walking tour in Rome which was very informative and very interesting. The tour was broken up into the morning and afternoon section (so that you would have time to go to lunch) and showed the highlights of New and Old Rome. We did end up spontaneously buying a tour for the Florence Duomo because the line was atrocious and the tour guides came up to us and offered a discounted student rate with skip the line access for a very reasonable price (I want to say it was only about $20 euros per person or maybe even less) so we went ahead and did that tour.

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A picture from the Cinque Terre tour. 


I am planning on writing a separate post about packing for a big trip but with Italy there is one thing I want to emphasize – pack comfortable shoes. I wanted to look cute in pictures and wear cute dresses and outfits and my feet were not happy with me. I’m pretty sure about day 2 I completely switched over to Keds and Toms because I just couldn’t handle all the blisters anymore.

*Make sure you pack clothing that covers your shoulders and knees if you plan to visit any churches and especially if you plan on visiting the Vatican. If you are not covered up, you will either get turned away completely or will have to buy something from one of the street sellers so it’s best to just avoid that situation altogether.

Time to Go

We went at the end of July and our trip crossed over into August and I am going to go ahead and rule that a “bad time to go” to Italy because it was blazing hot. Not to mention, I don’t think shade exists in the city of Rome so if you want to actually explore and not constantly have to take a siesta (aka an afternoon nap or afternoon retreat to your hotel to escape the heat), then I would recommend going a different time of year. My research is pointing towards October being the best month temperature wise to visit Italy.

Miscellaneous Tips

There are scammers everywhere out on the streets – they will try to shove roses in your face and act like they’re free and then demand payment. My best advice for this is just don’t even make eye contact and ignore these people. They are all over the place trying to sell flowers, selfie sticks, hats, etc.

If you do want to buy something on the street – bargain with the sellers. Name your price, they will say no and you can start walking away.  After that they’ll try to chase after you and agree to knock the price down some. If you don’t have to deal with them though, I would recommend buying things in shops (they have affordable souvenir shops everywhere you go) instead of dealing with street sellers.


Overall, this was the best trip I’ve ever been on and I highly, highly recommend traveling to Italy.  Like I mentioned earlier, I will be writing separate posts about each city – Milan, Venice, Rome, Florence and Amalfi Coast (Praiano) so stay tuned!

4 Comments Add yours

  1. Chris says:

    I can’t wait to go someday!

    Liked by 1 person

    1. You should definitely go! It’s an amazing place!


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