10 Day Italy Itinerary

May 3, 2018

It’s been almost a year since the last time we visited Italy, and boy, am I ready to go back! The second time was a bit different from the first, but equally as amazing. Our first time to Italy was just Casey and I, and we visited Rome, Amalfi Coast, Siena, Florence, Venice, Bellagio, and Milan. You can read all about that trip here.

This past time, Casey and I traveled with our good friends, Anthony and Rachel, and then also met up with one of my best friends, Teresa and her husband, Dane while they were on their honeymoon for a couple of the days. We did Tuscany, Cinque Terre, Florence, and Rome.

Here’s a recap of our trip along with some highlights and recommendations…


Days 1-3: Tuscany

Where we stayed: Hilton Grand Vacations Club at Borgo Alle Vigne, Casanova 11, Selvatelle, Terricciola

Casey and I are Hilton Grand Vacation owners and have been waiting for this particular property in Tuscany to be available. We stayed in a two bedroom apartment. It had a little kitchen, it’s own washer/dryer, and a nice size living room and dining room. It was absolutely perfect for what we needed. 

This property is just outside a small town called Peccioli. We were recommended to eat dinner at Pasticceria Ferretti on our first night. Honestly, that meal was quite possibly one of the BEST meals I’ve ever had in my entire life! We all shared a bunch of dishes; Cacio e Pepe, beef, some different appetizers… and of course a homemade tiramisu. Half of the restaurant is a bakery/pastry shop. A fun fact… the owners of Eataly in NYC wanted to import Pasticceria Ferretti’s biscotti, but the owner told us that there was no way she could produce the quantity they needed without jeopardizing the quality of her biscotti, so she declined their offer. The restaurant was of course family run…. we saw three generations while there. Again, the food was beyond fresh and delicious, AND it was SO AFFORDABLE!! We ate there a second time because it was that good!

Highlights and Recommendations

Wine Tours: Sant’Agnese Farm: [we ate lunch here] & Tenuto Torciano, San Gimignano: [while we were full from lunch, we still ate the lasagna they offered as a mid afternoon snack/second lunch, and it was worth every calorie]. PS, Tenuto Toricano does private wine tastings in the US.  You may have seen from my Instastories, but we had Lillo [from Tenuto Torciano] come stay with us and host a private tasting in our home with 30 of my friends. It was SO.MUCH.FUN. and I highly recommend doing that if they offer it to you after you visit them. Their white wine is my favorite white wine of all time [I usually prefer reds].

Car Service: THE NICCOLI LIMOUSINE GROUP: www.niccolimousineservice.net  We did have a rental car [actually a minivan], but opted to hire a car service for the day that we were wine touring around. Obviously we weren’t going to drink and drive, and the driver was very knowledgable on the area and was able to recommend some good spots for us.

Private Tour Guide: Natale, natale.cerbara@gmail.com. We used him our first time in Italy and he was great! He actually had picked us up in Siena, gave us a private tour all throughout Tuscany, and then dropped us off in Florence at the new hotel we were checking into. It was smart to do it this way because it saved us a few train rides and taxis. 

Towns to Visit: Depending on where you stay, I would research or ask around to see what medieval town is closest to you. Some of our favorite moments were spent in Peccioli which is never a place we would have visited if it weren’t for the simple fact that not much else was around the Hilton property. I don’t recommend traveling to Peccioli specifically, but if you happen to be in the area, check it out!

Siena: one of our favorites

San Gimignano: can’t miss

Montepulciano and Montalcino: we never ended up making it to either of these cities unfortunately. We most definitely will next time!

Hilton Grand Vacation Tuscany Italy, Via di Casanova, 11, 56030 Selvatelle PI, Italy

Hilton Grand Vacation Tuscany Italy, Hilton Grand Vacations Club at Borgo Alle Vigne

Tuscany Italy Itinerary, Tuscany in Spring, Italy Travel Guide, Tenuto Torciano Winery Italy, Sant’Agnese Farm wine tour best vineyard in Tuscany, Italy, Italy wine tour Sant’Agnese Farm wine tour, Tuscany Italy wine tour

Tuscany Italy wine tasting tour, Italy Itinerary

Tuscany wine tasting

tuscany peccioli pizza

Siena Duomo, Siena travel guide  

Siena Italy food, Oggi Porchetta siena


Day 4 – Monterosso, Cinque Terre

We [well, I actually] drove our minivan to Monterosso, and it took around two and a half hours. Parts of the drive were super easy, and parts of the drive we thought we were going to die! I’m only semi exaggerating. There is a parking lot and garage in the very beginning of Monterosso, and from there we had to walk to our hotel, which wasn’t far at all. We stayed at Albergo Degli Amici. Nothing fancy, but perfectly fine for what we needed. It was a tiny room with a full bed and two twin beds. I will be honest and say that it would have been interesting had we brought all of our luggage with us, but we actually left the majority of our stuff back at the Hilton since we were returning there the next night. We opted to have an overlap with our hotels in the event the weather was really awful and we didn’t end up going to Cinque Terre. We all had agreed that a day trip to Cinque Terre wasn’t going to be enough time, and I definitely think we made the right move by staying the night. In fact, I kind of wish we had another night there.

We hiked from Monterosso to Vernazza, and from there explored the rest of the Cinque Terre towns [via train]. We spent time in each of the towns… eating, drinking, and exploring. We got back to our hotel kind of late, so showered quickly and went back out for a late dinner.

Day 5 – Monterosso, Pisa, Tuscany

The following morning we enjoyed walking around Monterosso a little more. They were having their yearly lemon festival which was the cutest thing ever! Tons of kids and families selling lemonade, lemon cakes, lemon everything; dancing to music and singing Justin Bieber’s newly released Despacito. It was seriously one of my favorite moments.

Monterosso, along with the other towns that make up Cinque Terre have such charm and beauty. I don’t have a specific restaurant to recommend to you guys, but all of the food we ate was fresh and delicious. We did however, grab some sangria and bruschetta at a cool outdoor bar called Nessun Dorma in Manarola that I recommend if you want a chill spot to grab a drink. The location is perfect for sunset watching!

Cinque Terre Monterosso restaurant

Tuscany Cinque Terre Monterosso restaurant, Italy Travel Guide

tucany cinque terre view, Cinque travel guide by Jaime Cittadino

tuscany cinque terre view, cinque Terre hike

tuscany cinque terre vernazza, riomaggiore, five towns

Monterosso, Italy Albergo Degli Amici

tuscany cinque terre lemon festival Monterosso

tuscany cinque terre monterosso lemon festival

tuscany cinque terre monterosso travel guide, where to stay in Cinque Terre

tuscany cinque terre Monterosso travel guide

From Monterosso, we drove straight to Pisa…

Our goal was to get in and out of Pisa as quickly as possible. We were a little tired and hungry, and wanted to get back to our place at Hilton to hang out by the pool and relax before dinner. BUT, we were all super impressed by the leaning tower [it leans so much! Pictures don’t do it justice]. It was one of those things that I’m glad we did, and would maybe go again later in life when the kiddos are older. It’s super touristy and there’s not really anything else around there, but again, I think it’s a place to go see if it’s not too far out of the way for you.

pisa italy, italy itinerary, Jaime Cittadino

Pisa, Italy guide

Leaning Tower of Pisa, Italy review

pisa, italy review

Hilton Grand Vacations Club at Borgo Alle Vigne

Days 6 & 7 – Florence

Where we stayed: Airbnb’d @ Via de Bardi 49, Firenze, Toscana 50125. 2 bedroom apartment right on Ponte Vecchio. Highly recommend!

One of the things I love about Florence is that it’s easy to navigate. I was amazed by how much we remembered where things were from our first visit years ago. There are tons of great places to shop. There are tons of great places to eat! Florence is definitely high on the list of my favorite cities!

Restaurant Recommendations: make reservations for the following…

La Cucina del Garga

Trattoria l’ Parione

Il Santo Bevitore

Golden View: stop in here to grab a drink before dinner

Favorite Leather Shop: Massimo Leather, Borgo La Noce 13R 50123 Florence, Italy

Best Sunset Watching Spot: Piazzale Michelangelo

Things to Do:

Climb the Duomo and/or Giotto’s Bell Tower to see views of the whole city

Boboli Gardens

Walk along Ponte Vecchio before and/or after dinner when it’s not as crowded

Grab pre dinner drinks at the Westin Excelsior [make a reservation if you can]

Vintage shop







tuscany florence ponte vecchio view

Piazzale Michelangelo, Florence, best view in Florence

Days 8, 9, & 10 – Rome

Where we stayed: Airbnb’d @ Via del Corallo, 12 4 piano, Rome, Lazio 00186. 2 bedroom apartment in the heart of Navona [one of my favorite parts of Rome!]. Highly recommend!

We LOVE Rome!! L-O-V-E Rome!! We fell in love with the city the first time we visited back in 2013, and last year’s trip reconfirmed our affection for it. As mentioned before, Navona along with Trastevere are my two favorite areas of Rome. I honestly think three days should be the minimum amount of time when traveling there because you will/should want to explore the actual city outside of the main tourist attractions. 

Do not skip the Colosseum. It is incredible!

Restaurant Recommendations:

Hostaria Costanza: Eat here and thank me later. The restaurant is located in ancient theater remains older than the Colosseum. It’s a hidden gem that’s favored among locals and celebrities.  It’s so good, you might want to eat here twice! If I could recommend one restaurant only, this would be it!!

Alfredo alla Scrofa: “The Original Fettuccine.” Come here if you love fettuccine alfredo. 

Antica Taverna: sit outside if you can

Best Gelato: Frigidarium

tuscany rome trevi fountain


Rome, Italy Travel Guide, Colosseum Rome




tuscany hostaria costanza rome best restaurant



For information on what I packed, check out my ITALY PACKING LIST post here.

For details on our first Italy trip and other cities, visit here.

If you have any questions at all, please leave a comment below!

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