Italy Travel Guide


A month ago we ventured out on our first trip to Italy.  If you follow along on Instagram you may have seen some snippets from our adventure but today’s post is a full recap of our entire trip! I have yet to write a post like this so if I leave anything out/you have any questions leave a comment and I’ll be sure to respond.

The most common response I received from friends, family and coworkers when I told them about our trip was “You planned it yourselves?” While it does get a tad exhausting to map out travel plans, especially to several cities, I love doing the research it definitely gets me even more excited for the trip. We first figured out which cities were on our list to visit and then how many days we would need in each city. We chose Rome, the region of Tuscany and lastly Venice. We also planned to take day trips to Pisa and Florence while we were staying in Tuscany. Yay for crossing more cities off our list!  I’ll break this post down by each city/town that was stayed in, what hotel we stayed in and what activities we did on each leg of the trip.



The Colosseumslip-dress-1-of-1-14


St. Peter’s Basilica


Dress: Loft // Sandals: Urban Outfitters // Bag: Old Navy

We started our trip in Rome as we found it was the cheapest airport to fly into.  It was actually even cheaper to fly into Milan but since that wasn’t a top destination on our list we nixed that option.  We landed at about 12:30pm on a Thursday afternoon and stayed in Rome until Saturday.  This gave us just barely two days to explore the city and check out the major historical sites.  It was busy but very doable.  We actually took a red-eye flight from NY and neither of us slept much so after getting checked into the hotel and committing to resisting a nap, our first stop was iced coffee.  That was the first and last iced coffee in Italy.  It was a bit of a struggle to find good coffee in Italy as they seem to serve it sweetened and I do not drink any sugar in my coffee….in case anyone was wondering about my coffee struggles.

Where We Stayed:

Boutique Hotel Roma

Our hotel was walkable from the train station (about 1 mile) and there were lots of restaurants within walking distance.  We did have to take the train to Vatican City but we were able to walk from the hotel to the Colosseum and to the Trevi Fountain.  The room itself was pretty small, but I did read that small rooms are quite common in Rome.  Breakfast was included and they did in fact have American style coffee…score!  Our only complaint/concern about the hotel was the owners request to have the keys dropped at the front desk every time we left the room.  It was a bit strange to us to have to leave our room key with the front desk.  We were told that it was safer with them in case we lose it while we are out exploring.  Fortunately we voiced our concerns about this policy and were allowed to travel around with the key.

What We Did:

Being that we had limited time in Rome I made a list of each place we needed to visit and attempted to plan it all out once we arrived.  The hotel gave us a map and some tips on how to get to each attraction.  We visited the following:

  • Trevi Fountain- It was very crowded but a must see.  We didn’t spend much time there because of the amount of people but had it been less crowded I would have opted to grab some gelato and sit around the fountain for a bit.
  • Colosseum- You must buy tickets to enter but you don’t necessarily need to purchase them in advance.  We visited the Colosseum around 4 o’clock the day we arrived in Rome.  We waited in line for 20-30 minutes in order to buy tickets and enter.  It was definitely a site to see and we didn’t need more than an hour to explore.
  • St. Peter’s Basilica/Vatican City- If you are visiting Vatican City I highly recommend going to St. Peter’s first.  On the way out you can buy tickets for the Vatican Museum which will save you from waiting in line.  I was quite confused while researching prior to our trip but we found that no tickets are required to get into Vatican City and St. Peter’s yet you will need a ticket for the Vatican museum.  We paid a little more in order to purchase tickets for a certain time slot.  When we arrived at the museum we were SO glad we decided to do that as the line (which was all outside) was pretty long and it was in the 80’s that day.
  • Vatican Museum/Sistine’s Chapel (the Chapel is within the museum)-  Many people were on guided tours or using audio tours but we were totally fine exploring at our own pace.

**For both St. Peter’s Basilica and the Vatican Museum you must wear appropriate attire.  This means covering your knees and shoulders.  There is a chance of being turned away.  I opted for a midi dress and a light scarf which I wrapped around my shoulders.

I should note that we were able to accomplish all this within the two days because we did not take any guided tours.  There are guided tours of many of these historical sites yet they are often long and may require advanced booking.  We both prefer to tour the sites at our own pace, but that’s just our personal preference.  If you enjoy guided tours I suggest researching options before your trip.

Our Favorite Restaurant:

My most memorable meal in Rome was at Sofia.  I honestly can’t remember the name of my dish but if I could rename it I’d call it ‘pure deliciousness.’




Antinori Winery (Dress: H&M & also comes in black)




Sunflower Fields in Cerbaia


Castellina in Chianti


a quick stop in Livorno with this model


The Duomo


View from Piazalle Michelangelo

florence strolling through Florence

pisaA smidgen of the leaning tower of Pisa

Tuscany is a very large region and I struggled when researching the best place to stay.  There are so many small towns and some larger cities.  We were slightly limited because we booked our trip so last minute, it was kind of a blessing because had we had endless options I may have taken weeks to decide on a place to stay.  We ended up in Castellina in Chianti.  I promise I based my decision off of more than just my love for Chianti.  This small town is about 40 minutes from Florence and 90 minutes from Pisa.  While researching Tuscany I quickly learned that we would be doing a fair amount of driving regardless of the town we chose to stay in, mostly because we wanted to explore more than just the one town itself.

Where We Stayed:

Hotel Colle Etrusco Salivolpi for 3 nights and Borgo Di Pietrafitta Relais for 1 night.  The two hotels were roughly 7 minutes apart but I couldn’t resist staying at Borgo Di Petrafitta Relais for the one night because it had an amazing infinity pool overlooking the countryside.  They did not have full availability for the entire time we were in the area which is why I chose the first hotel for a few nights.  This actually worked out well as we found that Hotel Colle Etrusco Salivolpi had better customer service.  We stayed in a one bedroom apartment at Borgo Di Petriafitta and I would definitely recommend it if you’re visiting the area and looking to have some meals within your room.  It would also work well for families as there was plenty of space within the apartment as well as a game room and grill for barbequing on the property.

What We Did:

We had three full days in Tuscany and decided to make the very best of it.  We arrived on a Saturday and chose to enjoy some wine at the hotel before driving into town (also walkable) for dinner.

  • Pisa- On Sunday we drove out to Pisa for a day of exploring.  We actually found the town to be a bit underwhelming but the Leaning Tower of Pisa was on our list of things to see.  After visiting the tower we took a quick drive out to the coast in Livorno where we walked around the Terrazza Mascagni, a checkerboard print stone terrace, on the waterfront.
  • Florence– On Monday we headed into Florence to see the Duomo and explore the city.  We didn’t take the opportunity to climb the Duomo because it was extremely hot that day and I have read that it is a bit of a narrow stairway.  We opted to take in a view of the city from Piazzale  Michelangelo.  That night we ate one of our favorite meals before heading back to Chianti. Details on that below!
  • Winery Tour and Tasting- What’s a trip to Tuscany without a winery tour?  We toured the Antinori Winery, one of the largest producers of wine in Italy.  It was definitely the most modern place we visited in Tuscany.  The establishment is hidden on top of a hill and was 100x larger than we expected.  This is a huge production and we were able to take an hour tour of the facility.  We did book this about 2 days in advance on their website .  There is a restaurant located on the rooftop of the winery but unfortunately we did not have time to stay for a bite to eat.
  • sunflower field- This was not planned but I can’t leave it out as it was definitely a highlight of the trip for this sunflower lover!  I had hoped we would see some of the infamous sunflower fields but knew it may not happen as sunflower season had passed and we had driven by several fields of dead sunflowers (may they RIP).  On our drive to Pisa we stopped for breakfast and I grabbed a gelato.  Driving through the Italian countryside with my gelato in hand I was literally telling myself ‘life could not get any better right now’ and BOOM there they were, an endless field of my favorite flowers.  Jeremy knew to immediately pull over so I could frolic amongst the beauty.  The pictures really speak for themselves, this was one of my favorite parts of our trip.

Favorite Restaurants:

Our two favorite meals were at La Taverna di San Guiseppe in Siena and La Giostra in Florence.  Both require reservations.  We saw many parties get turned away from La Giostra if they didn’t have reservations.




Gondola after gondola after gondola




Pizza at Rizzo


After dropping our rental car off in Florence we hopped on the train for a two hour ride to Venice.  After lots of sightseeing in Rome and driving throughout Tuscany we were excited to have some downtime in Venice.  We had no plans other than to walk the mazes streets and explore the city…one pizzeria at a time.

Where We Stayed:

Our last two nights in Italy were spent at the Duodo Palace Hotel and it ended up being my favorite hotel of our trip.  I am quite picky about hotel rooms as I get a little weirded out thinking about how many people sleep in those beds and use those same sheets.  Currently cringing just thinking about it.  Either way, this hotel felt SO clean and we were pleasantly surprised to have landed the only room in the hotel with a balcony overlooking a canal.

What We Did:

  • Gondola Ride- This was a must.  I knew it was a bit overpriced at 80 Euro for a half hour but I could not leave Venice without a gondola ride.  It was definitely a tad overrated and our gondolier was on his phone while rowing us around #rude, but it was still a fun memory!  The gondolas are way fancier than I had expected, fur seats and shiny red interior, so lavish.
  • Ate food. YUP, we really did just walk around enjoying the last two days of our trip.  It was the perfect ending and we were definitely exhausted by this point.

Favorite Restaurants:

Dal Moro’s – delicious pasta to go and the staff were so friendly!

Rizzo- I cannot find the a website or trip advisor link for the life of me but the pizza here was SO good.



& that’s a wrap! If you are planning a trip and have any questions don’t hesitate to reach out.  I’ll happily live vicariously through your travels…while helping you plan!




  1. October 10, 2016 / 11:00 pm

    jess–well i had to stop by and see all these amazing photos since you decided to go to italy and get married besides meeting me in boston! lol, JK. italy sounds amazing and has been on my bucket list for years. i can only imagine how the food tastes there, i would literally eat everything and pasta or pizza in the states would never taste the same! also, again congrats on the engagement, i am beyond thrilled for you (oh and Lo! she got engaged too!), the sunflower field is def my fave photos. xoxo,

    janna |

    • Jessica
      October 12, 2016 / 10:29 am

      Haha I promise I won’t ditch you ever again! The food was beyond amaze and the sunflower field was sooooooo dreamy. I guess it’s engagement season here in CT, haha, so happy for Lauren too!


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