I spent just under twelve magical days visiting Italy for the first time in early June, the first half of my trip with one of my best friends and the other with my little sister who recently graduated from college! I was able to visit a number of cities, from Venice down to Portofino, and found some amazing gems along the way. I'm so glad I went towards the beginning of the summer, because by the end of my trip the crowds started to get very intense in the main cities and landmarks. I'm sharing some of my favorite images, destinations, travel tips, and an overview of my five-city Italy itinerary below with all the places I would love to visit again!

Five City Italy Travel Itinerary

May 29
Landed in Venice
May 30
Train from Venice to Verona for a winery tour
Train from Verona to Florence in time for dinner
May 31
Wake up in Florence
June 1
Train from Florence to Santa Margherita
Ferry from Santa Margherita to Portofino for a day trip
June 2-3
Explored Florence with my friend
June 3
Train from Florence to Rome for one night, met-up with family
June 4
Train from Rome to back to Florence with family
June 6-8
A few more days in Florence before heading home

(From top-left: Residenza La Loggia, the Grand Canal, walking views, the garden courtyard of Aman Venice)

Venice Travel Tips

We stayed at Residenza La Loggia in Venice, which ended up being the most charming bed and breakfast with rooms that were fully upholstered from headboard to wall – ours in the fabulous damask you see above. It felt very Venetian, and the breakfast they served was incredible. It also wasn't expensive, so I would highly recommend it. When we first landed we headed over to the Aman on the Grand Canal, which has the loveliest garden bar with views of the gondolas – without the noise and crowds of Venice's tiny streets! It was the most peaceful, refreshing way to start our adventure, so definitely worth the $30+ drinks. Otherwise, everyone I talked to recommended just getting lost in Venice's streets and I would definitely say the same thing.

Tenuta Santa Maria Winery

To break up the train ride from Venice to Florence, we stopped in Verona for the afternoon. It was a great chance to see a smaller town in northern Italy and a beautiful part of their wine country. This area is full of vineyards, and we stopped by Tenuta Santa Maria for a tour of this centuries-old winery and a tasting from their family-owned vineyard. The villa tour was my favorite part, which had one of the most incredible trompe l'oeuil ceilings I've seen.

(From top-left: view of the city from the Duomo clocktower, the sculpture room in Galleria di Accademia, La Menagere restaurant, the Cantinetta Antinori courtyard)

Florence Travel Tips

I spent the bulk of my trip in Florence, and it's so hard to pick favorites from this beautiful and historic art-seeped city, but here are a few. In terms of your key sightseeing, don't miss the Galleria di Accademia (but do make a reservation beforehand), not only for the statue of David but also for the incredible sculpture gallery full of busts, plaster casts, and sculpture fragments. My favorite museum was probably the Uffizi Gallery, containing a dizzying portion of the Medici family's collection of Midieval and Renaissance artwork. If you want to get your steps in, the clocktower at the Duomo was definitely the best central view over the city. For a view from across the river, I would recommend the Villa Bardini gardens over the crowds at the Michaelangelo steps.

There were some incredible restaurants in Florence, but La Menagere was one I visited more than once for lunch – it's a cafe, bar, and unique home decor shop with a warren of beautifully-designed rooms to explore. I also really enjoyed dinner at Cantinetta Antinori, where I discovered new favorite Tuscan specialty: Pappa al Pomodora (a tomato-bread puree soup). My favorite way to enjoy an Aperol spritz was to go to any of the hotel bars along the river (any of the Feragamo Lugarno Collection hotels are a good bet), offering plush settings and beautiful views at sunset. The best gelato? Make sure it's covered in the store (not visible in a display) so that you know you're getting the highest milk fat – and if you're on the left side of the river after dinner you'll want to try local-favorite Gelateria Della Passera.

Florence had some cool speakeasy-style bars, including 1920's themed Bitter Bar in the center of town and Rasputin across the river, which is worth the taxi ride over. It's a true speakeasy where you have to ring a doorbell and wait for someone to let you in, after which you're led down a candlelit staircase to a basement setting inspired by a Russian hermitage (hence the name). It featured very unique cocktail flavors with an extensive whiskey collection, and a fantastic ambiance.

(From top-left: Soho House Rome, inside the Victor Emmanuel II Monument, Osteria degli Amici, the Villa Borghese Gardens)

Rome Travel Tips

While I only spent 24 hours in Rome, I got to spend plenty of time walking through some of the most significant monuments around Trajan's Market, the Victor Emmanuel II Monument, Capitoline Hill, and the Trevi Fountain. The crowds were definitely more intense here than in Florence, so be prepared for packed sidewalks! Walking up to the monument stumbled upon Galleria Doria Pamphilj, which was an incredible hidden gem. It's a large private art collection housed within a palazzo (my favorite way to enjoy art), and just walking through the entrance was incredible as you could see the procession from public from private from the carriage entrance.

I stayed at Soho House Rome which was an amazing break from the smaller accomodations in Florence, and had amazing views over the city from the rooftop. I met up with my mom and sister here and we had dinner at Osteria degli Amici, which felt very local and had recently been renovated. In the morning we took a stroll around the Borghese Villa Gardens before hopping on the train, which was the perfect place to walk and enjoy a panini or pastry among beautiful statues and fountains.

Portofino Travel Tips

Getting to Portofino is not the easiest as you have to take a ferry (often crowded with cruise travelers) or a bus down the coast to get to this teeny tiny port town, but it's so worth it. I might even go as far as to say that our day in Portofino was my favorite part of the trip! When we got to the port, we went all the way around to the left side (away from the crowd) and ate lunch at the Strainer Restaurant, which has the best views across the port of the town's distinctive colorful buildings with painted trompe l'oeuil architectural detailing. We then took a 10 minute walk around the port, up the stairs and onto the road to Baia Cannone, which is the best place to go swimming. It is a small rocky beach below the Hotel Piccolo. Swimming in this little inlet was such a dream! For more views from this cliffside town, you can climb up to the Castello Brown. Otherwise, there are cafes, restaurants, and shopping to wander around and explore while your swimsuit dries.