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Italian Adventure: Florence, Amalfi, Taormina & Rome

One of our good friends was getting married in Sicily so what better excuse than to make a vacation out of it!  Jimmy and I packed in so many things in about 9 days and although it was a lot, we had the time of our lives!

Day 1: Rome -> Florence

We took an overnight flight to Rome followed by a 1.5 hr train ride immediately to Florence for our first part of the trip!  The trains are highly recommended and such a cool way to see parts of Italy we wouldn’t have been able to. We also had set up car services for the whole trip with Airports Taxi Transfers so we didn’t have to worry about having enough Euros on us to pay for all of the taxis everywhere.  The site is SO easy to use and was such a lifesaver. It was even cheaper than some of the shuttles that we were looking at through the hotels. Unfortunately, our flight was delayed which made us miss our original train to Florence (that’s a whole other story!) so we also missed our car service.  They were really nice about it and refunded us due to the circumstance. Florence isn’t too big so it’s easy to take cabs everywhere so we jumped in one outside the train station and headed straight to the beautiful Hotel Horto Convento. It’s a new hotel that was originally a convent which was pretty cool!  The location was also perfect for us. We were on the other side of the bridges but only 10-15 min walking distance to all of the attractions in the city center. It was nice to get out of the craziness and head back to our hotel at the end of the day since it was so peaceful.  It even came with a couple courtyards that you wouldn’t find across the bridge.  

Our first night, we made a reservation at La Giostra which was recommended by some of our friends that had previously visited Florence.  If you plan on going here, I highly suggest you make a reservation well enough in advance because we made ours months in advance and only had a couple slots to choose from for that night.  From start to finish, the meal was amazing. I ordered the pear ravioli and I’m still dreaming of it! Jimmy had steak and said it was one of his favorite meals of the trip. The restaurant was also in such a cool part of the city right near a lot of nightlife but of course we were too exhausted from a day of traveling so we went to bed right after our leisurely walk home!

Day 2: Florence

We started off the day early since it was our only full day in Florence.  We enjoyed a complimentary espresso and cappuccino in our hotel before heading out.  They even had champagne but we thought we would start off slow since we were heading to a wine tour later.  We walked up and down so many streets of the beautiful city before doing a tour of Accademia Gallery where The David is located.  We used Get Your Guide to book a reserved entrance and guided 1 hr tour so we didn’t have to wait in line and waste time. The tour is a must do since you learn so much that you wouldn’t have found out if you just went by yourself.  We realized we never ate a proper breakfast so we indulged in sandwiches @ All’antico Vinaio.  There is always a line outside of here and for good reason but don’t worry it goes by quick!  Once we filled up, we visited Ponte Vecchio and walked around more just admiring how beautiful all of the buildings were.  The Duomo is also so beautiful to see during the day and at night, but only the outside – the inside isn’t as pretty so don’t waste time/money there (thanks to our tour guide for that info!). We attempted to visit The Boboli Gardens but the line was out the door and it was raining so we decided to visit Giardino Bardini instead and the sun started to come out!  It was much less crowded and just as pretty – you could spend hours there! We also got an awesome view of the city that we weren’t able to see anywhere else.

We booked a winery tour through Viator in the Tuscan countryside by recommendation of our friends as well and it was so fun!  The pickup/drop off spot was the Florence train station so not far from where we were and there were about 25 of us. The tour included visiting 2 beautiful small wineries,  Fattoria Montecchio and Casa Emma where we had so many different wines and even olive oil! We ended up making friends with 2 other couples from NYC and another from CA – go figure!  The tour lasted about 4.5-5 hrs and it was a great highlight of our day!  Our original dinner plan was to grab some wine and pizza and watch the sunset at Piazzale Michelangelo where you are supposed to get the best view of the city but it had begun to rain again so we struck out there.  We didn’t have a reservation so we found the cutest restaurant, Osteria dell’Enoteca, which was only about a 10 min away from our hotel. Instead of a wine list, they bring you in their wine cellar where you then choose what wine you want – so cool! I might have also had pasta or pizza for every meal because why not so I had the tortellini and was in pasta heaven again! The tiramisu is also a must have if you’re a dessert lover. We ended up meeting another couple from America at the table next to us and spent the 3 hours we were there eating and chatting the night away.  It was a great ending to an amazing day!

Day 3: Florence -> Praiano

We only had a few hours left in Florence before we had to take the train to our next destination so we walked around some more because the views never got old and of course the sun was shining instead of raining the past 2 days. We found a cute lunch spot near our hotel to fill up on sandwiches and wine and then took the 3.5 hr train to Naples.  It was delayed so that was a bummer but luckily we had already set up the driver to pick us up so we immediately jumped in the car and were on route to Praiano – we didn’t care for Naples so were totally okay to get on our way.  Everyone always talks about the drive along the Amalfi Coast and they are not kidding. A couple times we had to close our eyes or look away because cars get so close to each other and go so fast in the narrow streets.  After about an hour and 45 minutes we arrived to Grand Hotel Tritone. We didn’t see much from when we got dropped off because you have to take an elevator down to the lobby since the hotel is in the cliff. The hotel and views it had to offer were unbelievable. Our room had a big balcony that we never got tired of going out onto every morning. After settling in, we had a glass of wine before enojying a sunset dinner @ Voce e Notte in Praiano. It was beautiful and the food was good! I had ravioli again, shocker!  We started off with yummy cocktails before dinner and stayed there until the end of the night enjoying wine, the view and chatting with the friendly workers, including the owner who lived in NYC (small world!).

Day 4: Amalfi & Positano

We booked a small half day inexpensive tour of Amalfi & Ravello through Postiano.com so since we were in Praiano, we took a cab to Positano and walked around for a little before going to our meeting point.  There were about 20 of us and our tour guide was so funny and entertaining which helped make it so fun. We learned all about the Amalfi Coast on our way to the town of Amalfi where we started off the tour with an hour boat ride, which was one of the highlights of our tour!  We saw so many amazing hotels, buildings and homes including Jackie Kennedy’s! Everything looked like a postcard – it was amazing! We were able to walk around the town for the remainder of the time we had in Amalfi so we grabbed some lunch at one of the local restaurants (more pasta) and then went back on the bus to head to Ravello.  Ravello is one of the cutest towns on the coast! We didn’t get to spend much time there because we found an amazing ceramic shop named Ceramiche d’Arte. We were in there for awhile picking out pieces to ship back for ourselves and our family. We enjoyed the view for a little before grabbing some gelato and heading back to our hotel, which the tour guide was nice enough to drop us off at!  It was so beautiful out that we took our hotel’s elevator down to the pool/beach area for a drink. We had dinner reservations back in Positano so we changed and walked around a little before dining @ Chez Black, which is right on the beach! Jimmy enjoyed veal while I stuck to pizza – delish!

Day 5: Praiano & Positano

Since we were on the go for most of the trip, we wanted one day to relax and enjoy our beautiful hotel!  We had perfect weather this day so we started the day with complimentary breakfast and then decided to walk down hundreds of steps to the beach instead of taking the elevator.  It was slightly nerve wracking but so cool to experience. We laid out by the beach/pool for the rest of the day enjoying aperol spritzs, wine and more pizza! We found out that you could take a water taxi from our hotel to Positano so we hopped on that! We got changed for dinner and found a cute restaurant called Lo Guarracino that overlooked the water in Positano.  Of course I had to give in to spaghetti again! The water taxi was awesome and so worth the extra 10 Euros that it costed verse a normal taxi.

Day 6 & 7: Praiano -> Taormina

We had an early flight from Naples to Catania, Sicily so we used the car service again to pick us up from Praiano -> Naples and again from Catania -> Taormina.  We had wedding festivities for the next couple days and enjoyed the cute town of Taormina!

Day 8: Taormina -> Rome

We ended up getting an earlier flight out of Catania into Rome so we had more time to explore!  One of Jimmy’s good friends ended up being in Rome the same time as us so it was fun to catch up and hang out since it was our last night of our Italian getaway!  Our hotel Hotel Della Conciliazione was in such a cute part of Rome and right near the Vatican. We grabbed wine and apps at the roof of Hotel Eden (amazing view) before going to dinner at Taverna Trilussa Trastevere.  This was probably our best dinner on our trip. We had so much amazing food including the best cacio e pepe I ever had – the chef even brought out his pan for me to eat out of!

Day 9: Rome

Our flight was later that night so we did not have much time to explore Rome.  I had been there about a decade ago (that sounds old!) but it was so cool to revisit everything.  We walked from the Vatican to the Pantheon to the Spanish Steps to the Trevi Fountain and finally the Colosseum.  We didn’t buy tickets to go in anywhere since we were limited on time but we saw everything that we wanted to in a couple hours!  We grabbed our last authentic Italian meal at Girarrosto Fiorentino before heading to the airport. It was one of our favorite meals and the perfect ending to a once in a lifetime trip.

We were so happy with our trip and wouldn’t have changed it for anything.  There is so much to see and do in Italy that you could be there forever!  Jimmy and I always say how you should visit new places before revisiting others, but I think we might have to make an exception for Italy.  We can’t wait to go back!

Need more inspo for your next trip? Check out our travel page!

xo A