Sample Itinerary: One Week in Italy

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I thought it’d be a great idea to narrow down my European Sample Itineraries to a country rather than the entire continent, so here’s my sample itinerary for one week in Italy.

I recently took a last minute – emphasis on last minute – trip to Italy with no real plans. I didn’t even settle on where I would visit until a couple weeks prior. Don’t get me started on when I booked actual accommodations. I would be traveling mainly on points from my Delta Amex and Chase Ultimate Reward Points so as not to break the bank on such a quick, weekend getaway. Plus I’ve been hoarding points since 2016, so why not finally use them?

Cost Breakdown 


RT Flight – NYC to Milan – 60k Delta points (the flight cost roughly $1285 at the time of purchase) plus $52 in taxes

Train from Central Milan to Levanto – 19.90 euros

Train from Levanto to Florence – 15.80 euros

Train from Florence to Milan – 23.90 euros


Hostel in Levanto (quick access to Cinque Terre by local train or hike) 48 euros for two nights

Hotel in Florence – $191.60 for one night (12,773 UR points)

Hotel in Milan – 117.68 for one night (7,845 UR points)


Me + Breakfast in Europe usually = pastry and tea. In Levanto I realized instead of a croissant, everyone was walking around with a weird piece of bread. After a disappointing breakfast offering at my hostel, I went on a hunt to find out what it was. I ended up at a bakery where people were carrying out slabs of it, walked over to the counter, and pointed at the glass, signifying that I’d like just one piece of the plain version. It was buttery and thick and tasted just like the bread used to make garlic bread sticks at your local pizza joint. ‘Twas foccacia. It was weird to be eating it first thing in the morning but it was a good start to the day. Another day I picked up a piece of fruit from the local market, a croissant from another bakery, and found a bench in a park to people watch and have breakfast.

In Florence, breakfast came with the hotel so I got my tea, bacon, and had plenty of fruit. Room Mate Isabella turned out to be a great choice for many reasons. When it came to Milan, I woke up at the crack of dawn and headed straight to the train station to catch my bus to the airport. I’d have breakfast in some random airport lounge.

When it came to lunch or dinner (aka either because I usually ate lunch too late for dinner or dinner early enough for it to be a late lunch) in the Cinque Terre Area I was spending almost 20 euros, whether or not I had a drink (which I didn’t). My lunch in Vernazza that consisted of a warm seafood salad and a glass of orange juice was 19 euros because the gentleman waived my “cover charge” for paying in cash. Insert all of the side eyes, but I always expect to pay 20 euros a meal in Europe, save for breakfast. When I Florence I walked around and as far from tourist attractions as possible in order to finder cheaper meals. So I had 8 euro pasta (dangerously delicious) and a glass of prosecco for about 15 euros. It was perfect. I ate every morsel and was so full I ended up skipping dinner. In Milan I wanted Chinese food and sushi so badly that I walked and googled until I found a place near my hotel. I spent less than 20 euros for a 6 piece sushi roll and some chili beef with white rice. I had an entire bottle of wine waiting for me that I needed to get back to.



I chose Milan to fly into because when trying to figure out where my points could take me on such short notice, Milan was the cheapest. I wish I had checked out Pisa or Florence because I’d already been to Milan and didn’t have a desire to return. It was just the point at which I’d enter and depart Italy. I immediately began googling places within a short train ride from Milan and set my heart on Cinque Terre. I’d completely forgotten that it was somewhere I’d wanted to see and I didn’t know it was just a 3.5 hour ride from Milan.

Okay, so Cinque Terre was on my radar. Once I realized the towns were hike-able and there was a good amount to see, I decided I’d spend two days there. And then go back to Milan? No, I didn’t want to spend several days in Milan. Surely there was another city just a train ride away that I’d love to see. After more googles (hehe, googles) I decided to visit Florence for just a night. Big mistake. 1. I always thought Tuscany was pure countryside and separate from Florence. Had I known that I’m a doofus and Florence is the capital of Tuscany, I literally would have spent my entire time there. Under the Tuscan Sun is one of my favorite movies, you see.


Day 1: Milan

If you’ve never been to Milan then I expect you to be completely unbiased and want to check out the city. It’s reasonable to fly into and a great starting point for travel to other cities, it’s also amazing for numerous day trips away from the city. I have absolutely nothing against Milan, I just don’t see the point in spending more than one day, maybe two there. Check out the Duomo and some amazing museums. Walk around. Shop! It’s a fashion capitol of the world. And be sure to eat all the pasta you can. You just got off of a long flight and you can even use this day to rest if you need to.

Days 2-3: Cinque Terre

From Milan, hop on the train to Cinque Terre, or if you’re feeling adventurous, rent a car for the week an just go. Hike through the five villages and make it a point to stop in each. How often will you get to return? The best part is that even though a couple villages look similar, they’re still completely unique. That’s the thing I love about Italy and why I could return again and again. Did you know this was my third visit? I’ve never been anywhere twice and here I was visiting Italy yet again. I could do it because everywhere I’ve been looks completely different than the last city. The Amalfi Coast, specifically Positano, is also known for super colorful homes on the side of mountains, but it looks nothing like Cinque Terre. There isn’t even an almost similar vibe. And I love each and every place just the same.

Days 4-6: Anywhere in Tuscany

I’m not going to lie, I fell in absolute love with Florence. I mean, I started thinking about living there. That’s how you know I was in love. If I step foot in a city and almost immediately start googling cost of living and apartment options, I can obviously see myself there. So, now I’m biased and recommended starting in Florence. However, you should definitely check out a nearby area such as Sienna, and more importantly the country side. Go on a wine tour or simply pick one vineyard and go spend the day. I’m currently imagining sipping glass after glass while nibbling on olives and ham and cheese. Mmmmm.

Day 7: Milan

On day 7 I expect you to be flying out, so you should probably get back to Milan this day or the previous night, depending on the time of your flight. I think it was an accident, but I booked a 10:30am flight and obviously needed to return to Milan from Florence the night beforehand. If you have a late flight, coming back to Milan earlier in the day gives you time to explore a little more and take in the city before leaving.

If you have somewhere in Italy you’ve always wanted to visit but it’s expensive to get there, I say pick the nearest popular airport (the one that usually has cheap RT flights) and fly into there. From NYC Milan flights can be as cheap as $450 and cheaper! You can head straight to the city of your choice, or you can do like I did and figure out all the hot spots around it. Visit those cities too and make a multi-city tour of it. It’s even a great chance to visit lesser known places, which is probably what I’ll do WHEN I return to Italy. I’m running out of cities to explore.

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