How To Plan A 14-Day Italy Itinerary: A Beginner’s Guide

Have you ever had to plan a trip last-minute? Did you hate every minute of it? I know I did. I had to plan a trip to Europe and didn’t know if I could go until the day of! Looking for hotels with a good cancellation policy was hell and it took me forever to decide where to go and in what order.

My boyfriend and I chose to only visit 1 country: Italy. We figured that since it was our first time not only traveling to Europe but also planning our own itinerary, it would be less of a headache not having to spend more time in airports than in the city itself.

2-Week Itinerary in Italy: A Beginner's Guide

So without further ado, I am going to walk you through how I single-handedly planned my 14 day stay in Italy and visited 7 different cities.

  1. Pick a country
  2. Look at a map to see which cities you want to visit and which are closest
  3. List them in order
  4. List the cities you can do as a day trip
  5. Use Trip Advisor or Rick Steves to figure out how many days you need in each city
  6. Book your hotels using a booking website. I used Hotels.com because of the free nights.

The Seven Italian Cities I visited

  1. Turin
  2. Venice + Burano and Murano
  3. Milan
  4. Cinque Terre (Monterosso + Riommagiore, Manarola, Vernazza, Corniglia)
  5. Florence + Pisa
  6. Capri
  7. Rome

I’m not going to lie to you it was pretty hectic and it was so wonderful at the same time but if I could go back and change anything I would. For starters, I would’ve gotten a train pass and would’ve saved a ton of money.

You should only stay in 5-6 cities. Adding any more destinations will cause too much stress of having to keep moving. I would have made some cities a day trip and spent more days in Florence and Rome because 2 days aren’t nearly enough.

Tips:

  • Buy the Eurail Pass
  • Buy a Sim card. A TIM sim card cost us 22 euros and lasted all 2 weeks.
  • Don’t be afraid to use public transportation!
  • Take only one medium suitcase and a big duffle bag you can use later if you’ve done too much shopping
  • Buy a polaroid and take it with you! You won’t regret it 🙂
  • There’s nothing wrong with not being into all the touristy stuff and the museums. Don’t force yourself. Have fun and get lost in the city instead.
  • Download Citymapper. Not all the cities are on there but the navigation is amazing!
  • Find hotels that offer free breakfast and wifi. It’ll save you some money and the hassle of having to wake up even earlier to find where to eat
  • If you’ve never gone on such a trip with your better half, it’s okay to fight. Traveling can be stressful but don’t let it put you down. I got lost, I missed my trains, one of our suitcases broke and I was given fake money but none of that mattered to me because it was, in no better words, one of the most magical trips we’ve done and I can’t wait for more!

 

P.S: All pictures were taken on my iPhone.

Turin

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Hotel: Hotel Galant

We landed in Turin and only stayed 1 night because my boyfriend lives and breathes soccer and if he missed the visit to the Juventus Stadium he would have pulled a bigger fit than a little girl without a pony on her birthday. Our hotel was an 8 minute walk from the stadium and about 30 minutes to the city by bus.

Sadly, and I was almost as heartbroken as he was, we learned the stadium was closed on Tuesdays and were leaving that same day for Venice. That being said, if you want to visit the stadium and museum make sure to check what days they close and the game dates. It would have been so amazing to see one live! We found a few awesome pubs to watch them at though!visiting-italy-1

Venice, Murano, & Burano

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Hotel: Hotel Stella Alpina Edelweiss

The city of love. I obsessed over every inch and every canal of Venice. All the islands are beautiful. We stayed in Venice 2 nights. The hotel was right next to the train station which was super convenient. Besides, I didn’t even want to think about having to climb in a vaporetto with our luggage at night. If you’re exploring the islands, wake up early and buy the 24-hour pass for the vaporetto. We visited Murano and Burano. The key is to go super early before the crowd gets there. It was so peaceful. I felt like we had the island to ourselves.

Tips: The GPS is shit. Try the Sepia al Nero (cuttlefish in black). Visit the cheap german pub by the train station. He plays Pink Floyd all day.

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Milan

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Hotel: Albert Hotel

Our main reason to visit this place was because my boyfriend had to visit the stadium. The hotel was great! For how much we payed, it was way nicer than I excepted and the breakfast was delicious. We stayed in Milan for one night. Personally, I wasn’t too much of a fan except for the cheap pizza place I found. I had a slice bigger than my face for breakfast, lunch, and dinner.

The Duomo was beautiful and all and the pizza (oh my fucking god, the pizza) was incredible but I felt like there was not much to see. Milan is very modern in comparison to all the other cities. We did, however, buy our weight in wine, cheese, prosciutto, and champagne with only 20 euros from the supermarket.

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Monterosso, Cinque Terre (& Riomaggiore, Vernazza, Manarola, Corniglia)

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Hotel: Hotel Suisse Bellevue

Our hotel in Monterosso was beautiful and I loved every minute of it. The view and our balcony was everything I had hoped for! I highly recommend this place and will be going back.

If you follow me on Instagram or Snapchat you probably saw that my boyfriend stayed in after we explored Monterosso. I went on to explore all 5 towns in Cinque Terre and had a beer in each stop. I traveled to Monterosso, Vernazza, Manarola, Riomeggiore, and lastly Corniglia. The views of Cinque Terre are heavenly and if the weather is in your favor you can hike to each town. I took the train, obviously.

Tip: First time traveling to Cinque Terre? Read this article. It really helped me plan where to stay and what to see.

Getting to Monterosso was hell. First, our train was cancelled. Then, we got off on the wrong stop and I left my boyfriends bag with everything he bought and all the food. I jumped on the first train back to where I thought I had left it. There was this couple I met who I’m pretty sure were trying to make me feel better but deep down I knew they thought I was an idiot for even trying. Then, as I lost all hope and walked back to the train I saw an Italian man walking back with MY bag in his hand.

I yelled at him and chased him down. He was yelling some Italian at me and when I got back to the hotel I realized he was trying to tell me he took some big ass chunks out of all my cheese BUT everything else was there. I was the luckiest girl in the world and nothing could stop me. Hence, my decision to have a beer in all five towns in 1 day. The next day I ran into the same couple in one of the five towns and they were more excited about finding my stuff than I was.
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Florence & Pisa

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Hotel: Affittacamere Chiazza

I wish I had stayed in Florence 3 nights but we only stayed 2 nights. There is so much to see, so many places to walk to, and so much to eat. Our hotel was right next to the Duomo. If you want to buy leather, silk, and food, go to the San Lorenzo Market. I regret so, so much not buying more of what I wanted while I was there because I thought that maybe I could find it in Rome but I was so wrong. I still get teary-eyed for not buying more silk scarves and truffle honey. You can make a lot of day trips around here such as Pisa or even Cinque Terre. Rent a car if you can! If I stayed longer I would have!

Tip: Eat paninis, lots of them. Go to “The Friends Pub”, and don’t bother staying in Pisa. Take take the train over there early in the morning.

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Capri, Napoli

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Hotel: Hotel Weber Ambassador

Everything is beautiful in Capri. All I wanted to do was walk around, visit every shop, and eat as many gelatos as I could. The view from this hotel was also beautiful! It was pretty pricey but totally worth it. You should rent a private boat if you’re with a group. You can see the entire island and unlike the other tour boats, you can swim in the Blue Grotto (for as long as you want). Unfortunately, the weather was not in our favor. Just an FYI, Capri can be a day trip from Rome if you’re staying a few days.

Tip: If you’re with more than two people rent a private boat. It’s only 120 euros for 4-6 people and you can go anywhere you want for 2 hours. Plus, you can swim and bring food or champagne with you too.

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Rome

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Hotel: La Maison Del Corso

2 nights was not enough time in the beautiful city! There is too much to see. I love getting lost in the city. You won’t believe how many markets and beautiful Italian shops you can find. If you ever travel with me I’ll be the one with a beer in hand and some bread in the other. Rome is definitely the place to wander. In my opinion, you should take the big red bus to do all the main attractions. Then, spend the rest of your days exploring. There was nothing extraordinary, but our hotel was one of my favorite ones and I highly recommend it! The room was cozy and the decor was pretty cute. Not to mention, the location was perfect! Out hotel was located on Via del Corso and super close to a metro station.

Foodie Tip: Find Knick Knack Yoda and have a burger! It was a mission to find but the best one I had. Try the one with truffle butter. You’ll thank me. Also, near the Colosseum look for Maccheroni Express. They make your pasta right in front of you and its delicious AF.

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Planning A Trip To Italy? Here Are The Hotels I Stayed In:

[show_shopthepost_widget id=”2089743″] If you liked this post please share it or pin it! It took me a pretty long time to write this so it means a lot and I hope you enjoyed reading about my trip in Italy! If you have any questions please leave them in the comments below.

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3 Comments

  1. November 7, 2016 / 11:23 am

    This post is super helpful for those of us who have no idea how to plan a weekend getaway, let alone a full on vacation! I can’t wait to implement these tips on my next trip! Thanks, girl!

  2. November 7, 2016 / 4:39 pm

    Wow! Such an amazing trip! This post is so helpful. I went to Europe before the age of smart phones and easy access to the internet, and it was so much harder to get around.

  3. Angelle Marix
    November 16, 2016 / 11:13 am

    Ahhh, I loved the pictures. I can’t wait to visit Europe again. My favorite city is Venice. It’s so cozy and unique.

    xoxo,
    Angelle
    http://www.dashingdarlin.com

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