Best of Italy: Highlights From Our 17 Day Trip

September 28, 2013

Bonjourno! Casey and I recently returned home from our belated honeymoon/early 1 year anniversary/ excuse to take off of work for 3 weeks/ vacation to Italy.  I can’t even begin to explain what an amazing time we had!  I have been fortunate enough to travel to some unbelievable places [London, Paris, Amsterdam, Barcelona, Ibiza, Israel, Hawaii to name a few] with pretty special people, but I have to say that Italy is probably my favorite thus far.

We were there for 17 days and nights in total which seems like a longgg time, but it honestly wasn’t long enough! There are so many places we didn’t get to see, but with that being said, we still had the best time ever. Every day was our favorite day!

We traveled a lot within the country, hopping around every 3 days or so to see and do as much as possible.  I don’t suggest our itinerary to a family traveling with small kids or a large group of people, but for us it worked perfectly. So here it is… the best of Italy and highlights from our 17 day trip…


Italy Rome Trevi Fountain, Travel Guide, Rome Guide, Best of Italy


We LOVED Rome and honestly could have stayed for weeks without getting bored!  There is so much to see and do tourist-wise [not a word, but you know what I mean]: Trevi Fountain, Spanish Steps, The Vatican, Colosseum, and Pantheon to name a few.

My favorite moments, however, were spent exploring the different neighborhoods, especially Trastevere and Navona.  We fooled a lot of people into thinking we were Italian. Our last name, Cittadino even means ‘citizen,’ but the second we opened our mouths, they clearly knew we were not from there. Rome is a large, crowded modern city, with tons of history and charm throughout.


Italy Rome, Rome Food, Best Rome Restaurants

Rome Italy Guide, Best of Rome, Best of Italy

Post Vatican.

Best Pizza in Rome, Dar Poeta Rome Italy, Rome Travel Guide

Dar Poeta in Trastevere. One of the best pizzas we ate!

Colosseum Rome Italy, Best of Italy, Italy Travel Guide

The Colosseum – a must go see!

Guide to ROME, Italy, Colosseum Rome

Best of Italy Travel Guide by Jaime Cittadino of Sunflowers and Stilettos

The Library restaurant Rome, Where to Eat in Rome Italy

The Library

Pierluigi Rome restaurant, Rome travel guide




If it’s your first visit to Rome, you can’t not visit all of the main attractions. My favorite was the Colosseum. It blew me away! We did our own audio tour which was totally fine! We toured the Vatican on our own as well, however, I think the experience would have been better had we booked a private tour in advance. It was very beautiful, but equally as crowded. I’m glad we went, but have no desire to go to again.


Make reservations for dinner if there is a specific restaurant you know you want to eat at.  We had an entire list of places to go to, but there were some days we decided to walk around and just wing it.  We didn’t have a bad meal in Rome.  Even the random places not on our initial agenda were delicious.  The black truffle pasta at Pierluigi was bomb-diggity and the service and atmosphere were the same. Our waiter informed us that they opened up another location in Brooklyn, go figure, but obvs the one in Rome is better because the food quality in Italy is better.  Everythingggg is just better in Italy!!

[Update 2017: Pierluigi was a big disappointment our second time visiting. We went for lunch and got completely taken advantage of. Their food is delicious, but it’s very expensive and the portions aren’t great. If I could recommend one restaurant in Rome, it would be Hostaria Costanza.]

Places recommended to us: Alfredo’s, Tullio

We stayed at the Waldorf Astoria Rome Cavalieri.  Beautiful, beautiful hotel.  The only downside was we had to take a cab or shuttle bus to get anywhere because it’s a little out of the way.  The hotel sits at the top of a hill and overlooks the city. At night the view is pretty magical.  I think next time we go to Rome, we’ll stay in walking distance to one of the neighborhoods we loved.  We were really bummed to leave Rome, but that’s basically how we felt about every place we visited.


Sorrento was next, but we stopped in Naples first to have lunch.  I mean…how can we not try pizza in Naples, the undisputed homeland of pizza?!!  And I love me some pizza!!!

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Case went with the classic Margherita. (Yes we got two, not realizing how huge they were.  That being said, we disgustingly did not leave a crumb behind, it was that good).  I forgot the name of the pizza I ordered, but it had one or two more types of cheese than the Margherita with some roasted tomatoes on top. Yummm.

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Pizzeria da Gaetano – hands down, best pizza.

We found Sorrento to be very charming and relaxing.  A complete change of pace from Rome and even more so, Naples.


View from our balcony.

Sorrento, Italy

Italy Food

Sorrento Italy

Casey Cittadino

Recommendations: La Antica Trattoria was our best meal in Sorrento.  Gelateria David has ridiculously delicious gelato, but then again, is gelato ever not delicious?  I normally don’t like very sweet beverages, but the Limoncello was so so good.  If you get motion sickness easily, take a dramamine before getting in a car or bus.  Seriously.  To say the roads are twisting, turning, and beyond narrow is an understatement.  I literally felt like I was on a rollercoaster, which I love, but can see why some people may not like that.  We liked our hotel, The Hilton Sorrento Palace, and would stay there again.  It was a quick walk into the center of town.


Capri Italy

Capri Italy

Dolce & Gabbana’s Yacht!

Capri Italy



Case was the only person who jumped in the Blue Grotto.

Capri, Italy


Capri, Italy


Casey Cittadino

Capri is stunning and definitely one of the most glamorous seaside getaways.  The shopping is uh-mazing.  I told Case we better get rich soon because I need a vacation home here pronto.


I wouldn’t necessarily call this next part of our vaca a “highlight,” but it was certainly memorable.  Last minute we decided to rent a car and drive to Siena which is 5 hours North, to avoid taking multiple trains.  Prior to renting the car, Casey told me he knew how to drive stick shift no problem.  He failed to mention that he drove stick shift on occasion for a few months back in college, like his Sophomore year, as in 11 years ago!!!  He claimed it was just like riding a bike.  Just like riding a bike my a$$ (pardon my language).  Remember what I said about the roads along the Amalfi Coast? Ya, certainly not the place to reteach yourself stick shift.  And the patience level of the locals as we stalled twenty times pulling out of Hertz was not very high to say the least.  I literally thought my life was coming to an end for about a half an hour.  I have to give Casey credit though.  It was probably the worst possible conditions to relearn stick shift, given how steep the roads were and the bumper to bumper traffic we had leaving the Sorrento and Naples area.  Lets just say he learned rather quickly and drove like a champ, and we got to Siena in one piece thank god.


Siena & Chianti

We absolutely adored Siena.  Stayed in the cutest hotel ever, Hotel Palazzo di Valli for one night before taking a wine tour throughout the Chianti region.  If you ever visit Siena, you MUST stay here!  This hotel was more of a bed and breakfast type place, with the most incredible view of Tuscany and best hospitality ever.  The two guys running it, Lorenzo and Giacomo couldn’t have been any nicer and it was a quick 10 minute walk into the main part of town.  Also, our meal at Trattoria Fori Porta, which is just across the street from the hotel, was arguably one of the best meals we had the entire trip, and probably the most affordable too. 

Siena, Italy

Sunrise from our room.


Siena, Italy


Siena, Italy

Obviously I had to throw up the crown. Zeta for life.



Oggi Porchetta.  This butcher shop was awesome!  The owner is a riot and introduced us to grappa.  One minute we’re eating an array of meats and cheeses, drinking Chianti Classico minding our own business, and the next minute the lights go down, a blacklight turns on with Italian techno music playing, and the owner starts dancing and saying “disco, disco.”  It was the most random, but fun place ever.

Italian Butcher Siena

Clearly we took photos when there is a huge sign that says not to. Oopsies.

Italian Butcher Siena

Siena, Italy

We got picked up by Natale, our tour guide for the day who gave us a private tour of the Chianti region.  First stop was a wine tasting at one of the farms, Sant’Appiano with homemade lasagna that Casey will not stop talking about.

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Tuscany Italy

Tuscany winery Italy

This is the owner of the farm and the lasagna maker. We wanted to take her home with us!

Next we visited Greve, a friendly market town and the ancient village and castle of Montefioralle.

Tuscany Italy

Tuscany Italy

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Tuscany Italy

Our last stop of the day was at Corte Di Valle, another winery.  We ate saffron or ‘zafferano’ cookies and drank wine directly from the tins!  It was so strong, but like everything else in Italy…delicious.

Tuscany Italy

Next Stop:

Florence ~ Firenze

Oh Florence, how I love thee.  I don’t have a favorite place in Italy.  Every place was my favorite, but as far as me choosing a place that I can picture myself living in long term, I think it would be Florence.  Yeah, I’m pretty positive it would be Florence.  Actually…Florence may be my favorite.

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I never realized I had such a fascination for doors, but almost every door we walked by, I told Casey that I wanted that in our future home.

Florence, Italy

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We stumbled upon this restaurant after the place we planned to go was closed for some unknown reason.  Everyone inside spoke Italian and the menu was only in Italian, so we figured it was worth a shot.  Case couldn’t wait for dinner to try the Florentine steak since everyone around us was eating it.  Boy, was it incredible!  (You guys must think I have some sick food addiction because I realize every other sentence is about food and how amazing it was).  I mean, that’s what you do on vacation, right? Eat, Drink, Shop, Walk, Take Photos. Repeat.  Or in my case, take photos during all activities.

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Florence Italy

Ponte Vecchio

Casey Cittadino



Ponte Vecchio

Casey Cittadino

Sunflowers and Stilettos

Florence Vintage Shops

Tons of great vintage shops in Florence.  Don’t mind my flip flops.  Wore heels the night before so my poor feet needed a break!

Florence Italy

Top of the Duomo!

Duomo Florence

Recommendations: Like Rome, we had an entire list of places that people recommended us to eat at.  Two of our favorite meals during the entire trip (for quality of the food and overall dining experience) were at La Cucina del Garga and Il Latini.  Il Latini doesn’t take reservations, so if you want to eat here, you have to show up as soon as they open which is 6:30pm I believe.  We closed the place down and were the last ones to leave.  One of the reviews on TripAdvisor says, “you’ll leave drunk, stuffed, and happy,” which is spot on.  Actually, now that I’m thinking of it, we were also the last ones to leave La Cucina del Garga.  We made friends with the owners of both places, per usual.  Everyone was super friendly!

For leather, go to Massimo Leather.   We got lucky and randomly stumbled upon it.  They are usually closed Sundays, but had opened specifically for a Rick Steves Tour.  They are top rated on Yelp and TripAdvisor.  Have top quality, good prices, not sketchy or pushy.  Needless to say, we both got beautiful leather jackets.

There is so much I can write about Florence, but I won’t.  Just do yourself a favor and plan to visit there in the next few years if you can.  You won’t regret it, promise.

Venice ~ Venezia

We met friends while in Florence, who live just outside Venice (shout out to Paola and Francesco).  Not surprising that we started talking to them because Casey complimented Francesco’s shoes.  Normal.  They were so unbelievably kind to meet us in Venice our first night with three of their friends, and show us around.  We had so much fun and hope that one day we can reciprocate the favor.  In Venice, its more of a common thing for the locals to bar hop rather than sit down for dinner.  We went to maybe 5 different places and grabbed a glass of wine and little sandwich or something to eat at each place, in between our own very personal tour of the city.  Venice gets extremely quiet at night, but busy and touristy during the day, so it was pretty great to truly explore it at first without the crowds.  As much as we loved Venice, I’m not quite sure it would have been the same experience had we not met our new 5 friends!  We’ve already talked about a future ski trip together in the Dolomites!

Venice Italy

Venice Italy


The next day Casey and I attempted to retrace our steps from the night before.  We found 3 of the restaurants we had been to and was so proud of ourselves!  Be prepared to get lost in Venice!  It was much more enjoyable and relaxing when we didn’t have a plan.

Venice, Italy

Venice Italy

2013-09-11 08.36.35 Jaime Cittadino

Rocking our new leather jackets. Leather Helmut

I want a scooter and I want this leather helmet.

Nutella Stand in Venice

Yes, the Nutella stand was in the courtyard of our Hotel.  We stayed at the Hilton Molino Stucky and got a free room upgrade to the Executive Suite which was awesome.  We would definitely stay back there!

Venice, Italy

View from the hotel pool.

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The Jewish Ghetto.

Recommendation: Trattoria Ca’ D’Oro.  We just stopped in for a glass of wine, some meatballs and grilled squid during our bar hop (2 days in a row).  It was packed for lunch and dinner and we were told that this would be a great place to have a sit down dinner which we didn’t end up doing.  It has awesome reviews on Yelp and TripAdvisor.  From the little taste we got, we’re certain their food is legit.


Serenity at its finest.  Picture Perfect.  Relaxing.  Gorgeous.

We stayed at a wonderful bed and breakfast, Il Perlo Panorama that overlooks Bellagio and Lake Como.  We absolutely would recommend this place to anyone planning on going there.  The owner is the cutest woman on earth and this property has been in her family for 4 generations.  This was the view from the window inside our room, not even from the balcony…

Bellagio, Italy

Bellagio, Italy

Bellagio Italy

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Bellagio Italy

Bellagio Italy

We are children.

Bellagio Italy

We made some more friends in Italy who were traveling from Connecticut.  Had such a great time with Vlora and Krenar!

Bellagio Italy

Bellagio, Italy

We seem to always find the crazy people. Hmm…

Bellagio, Italy

Jaime Cittadino

Varenna Italy

Varenna – across the lake from Bellagio

Bellagio Italy

Bellagio Italy

Bellagio Italy

Milan ~ Milano

We got a tease of Milan.  Unfortunately had one day and one night before we flew back home.  It was also raining which is never fun, but we didn’t let that stop us!  The shopping, oh my godddd, the shopping!  If this was our first stop on the trip I think we would have gotten ourselves into a little trouble.  The Zara Store, or I should say stores since they were everywhere, was the size of Macy’s in Manhattan.  We found a designer outlet.  Black leather Gucci booties that were PERFECT and only one pair left in my size.  As soon as I put them on Casey was like, “you need to get those.”  Even though they were extremely discounted, they were still a fortune, and certainly more than I could rationalize spending.  I was very proud of myself for resisting the urge.  Of course, now I have dreams about these beautiful shoes and kinda regret not buying them.  Again, after Casey makes us a lot of money and buys us that vacation home in Capri, we’re gonna find those shoes and buy them in every color they come in!

Milan Duomo

Milan Duomo Italy

And that’s the end folks 🙁

When I started writing this post, I had no idea it would be this long!  There is still so much more we did, and saw, and ate that I didn’t talk about or post pictures of (you’re probably thinking “thank god”).  It was the best trip I have ever been on and I’m so sad its over.  If anyone is planning on going to Italy, feel free to ask me any questions you have.  I’m not an expert, but am happy to share our experiences and the advice we were given prior to and during our trip.

Addio mie belle amiche!

Goodbye my beautiful friends!

Love, Jaime signature


Italy Itinerary, Where to travel in Italy, Italy travel tips, Italy honeymoon

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