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Living La Dolce Vita: Tips for Planning Your Italy Trip

Planning Your Trip to Italy + Our Itinerary

Ciao bellas (and fellas). I just returned from an amazing 10 days in Italy and, because many of you asked, wanted to share our itinerary and also some highlights from the trip.

First, I must give credit to our lovely travel agent, Melissa Rosenbloum. I highly recommend working with her to plan your dream trip (bonus: no cost to you).

Next, I’m going to outline the trip and then give some pointers on packing, so keep scrolling for those!

First Stop: Florence

We went to Florence, a city that had been described to me as Soho-like and very picturesque. These insights were spot on, and I was pleasantly surprised with how close our hotel was to the Arno River (a spot that makes for beautiful photos).

Upon arrival, we settled into the hotel (we stayed at the JK Place, which we loved for its proximity to the city center) and then went on a guided walking tour and stopped at the indoor market, which was fun and had a mix of actual vendors (downstairs) and prepared food shops (upstairs). We had some time after our tour and before dinner, so we took a cab to Piazzale Michelangelo to take in our first sunset. Dinner the first night was at a local Trattoria, 4 Leoni. Order the pear ravioli!

While we intended to go on a run around the city our first morning, our body clocks decided otherwise and we slept in! For lunch, we visited the Antinori winery the next day (about 30 minutes outside the city and a must, especially if you’re into modern architecture). We also took a tour. The winery is built into the countryside (literally built into a hill) and is quite spectacular to see.

I had a blow out that evening, and highly recommend Lapo Salon if you’re in need of some pampering. Quite possibly the best (and longest) scalp massage of my life.

For dinner we went to the very picturesque Belmond Villa San Michele. Amazing dinner and the views can’t be beat.

On Sunday, we did a bike tour of the city. Once I got my legs under me it was fun, but I’d recommend doing this on a Sunday morning as the roads were not crowded with cars (though by the afternoon, there were people everywhere!). We biked back up to the Piazzale Michelangelo, and stopped at a beautiful Rose Garden, which is close to the top (but can be easily missed by car).

After the tour was done we walked around the beautiful Boboli Gardens and did some shopping in the afternoon. This proved to be the day of gardens as we went to the Four Seasons Hotel for dinner and a drink and their gardens are just specular (and happen to be among the largest private gardens in Florence). My parents stayed at this hotel when they visited Florence last year and I am so jealous as it was truly beautiful.

On Monday morning prior to our trip to the Tuscan Countryside, we met and shot with our Flytographer (a service I highly recommend, whether for solo or family photos). We shot early as the lighting is the best, but it was SUCH a great way to see the city without any crowds. I loved Sonya!

Other sights to see/shops to visit: The Gucci Museum, Il Papiro (Gorgeous Paper), Flower Market (open on Thursdays)

Recommendations from my Instagram Fam: All’ Antico Vinaio (Get the Truffle Sauce), La Giostra, Gusta Pizza, Cammillo, La Terrazza (Top of the Continental, for Drinks), La Menagere (for Breakfast/Lunch), ZebGastronomia, Osteria Santo Spirito (Get the Truffle Gnocchi), Gelateria Della Passera, Tratoria Omero (Visit the Back Patio), All Antico Vanaio, Gelateria La Carraia, Mario (for Lunch), Aqua al 2 (for Dinner), Rooftop at the Westin (for Sunset), Trattoria dei 13 Gobbi (Rigatoni Gobbi), Harry’s Bar (for the Tiny Grilled cheese), Konnubio, Enoteca Fiorentina

Next Stop: The Tuscan Countryside

I’ll start by saying whether you choose Florence as your prime city or Rome, there are “getaways” you can easily do from any of the more major cities. For example, Hotel Il Pellicano is 1.5 hours from Rome and on my list for next time.

Since we had Florence on the front end, we decided to go into Tuscany, and stayed at a dream of a hotel, the Rosewood Castiglion Del Bosco. If you like wine, anywhere you visit in Montalcino would be worth it (as they are known for their Brunello).

Should you stay at this resort, book the pizza making class. It was such fun! We met a lovely couple (the four of us took the class together) and ended up eating our weight in pizza. We also got to tour the property’s organic vegetable garden.

The pool, gym, spa, and property are all truly amazing and the roses that surround are just breathtaking.

My Favorite Stop: The Amalfi Coast

We took a train from Florence to Naples, then got a car to The Amalfi Coast , specifically Positano (pro tip: take something if you get car sick as it’s quite the winding road experience).

There are so many hotels in Positano that are out of this world…Le Sirenuse, Hotel Il San Pietro, Villa Treville, Villa Franca…the list goes on. Try to make it a point to eat or get a drink at whichever hotels you don’t stay in.

We took a guided tour of the coast, stopping in Amalfi and most notably Ravello, where we spent the afternoon walking around and eating lunch at Villa Maria. There are several five star hotels in Ravello that are beyond breathtaking!

Worth noting: everyone is so happy to be there that they are beyond friendly and you’ll likely ending up running into people you know (or the same people on multiple legs of your trip, as happened to us).

We also took a day trip Capri (there are many ways of doing this, especially if you stay in Positano…you can take the Ferry from the beach, charter a boat, etc.). I wish we had more time to shop around as the shopping there was lovely. We ate lunch at La Fontelina (make a reservation for lunch and a separate reservation for chairs at the beach club!) While I preferred Le Club 55 in St. Tropez, this is a spot to see!

Finally, if time allows, schedule a Flytographer shoot as it’s a great way to ensure you get some decent shots if traveling with a pro camera isn’t your thing. Barbara and Claudio are fabulous to work with!

Other spots to visit: Casa e Bottega (for Lunch), Baby Bottega, Next 2 (for Dinner), Max (for Dinner)

Finally: 36 Hours in Rome

We stayed at the Hotel Eden (same family as the Beverly Hills Hotel). It was lovely and their restaurants are REALLY good (one of the best meals). Whether you stay there or not, be sure to hit Hotel de Russie to look around and for a drink. I found my new favorite drink the Sparking and Fashion at their Stravinkskij Bar.

Shopping is great near the Spanish Steps and we walked to the Colosseum and Pantheon but didn’t do any tours since we were in town for such a short while.

Now for some packing tips! I got many questions and inquiries about what and how I packed. It’s fairly simple: I sort of had a uniform for daytime and mixed it up at night. I stuck to white/neutral and mostly midi dresses (as I think these are more flattering with sneakers).

Check the scroller below for most of what I wore. This was a favorite dress. I wore these sneakers and these too (which are on sale). I only packed two pairs of heels, these and these (on sale, only a few sizes left) and two pairs of wedges (I only wore one pair, and only for the photoshoot). The best thing I bought on the trip (really the only thing) was a Gucci bag. This is the size I went with (many of you weighed in!). Of course, my hat was along for the trip (hat Stanley, if you will). My glasses were key as they weren’t so dark. This made my face visible in photos (which helps when you don’t do your makeup but want to look cute and been seen/vs. hiding behind black glasses). Also got a lot of questions about my lemon earrings. I bought them before the trip knowing how lemon-obsessed I would be once in Italy!

More questions? Comment below or message me on Instagram @bornonfifth! And, don’t hesitate to reach out to Melissa Rosenbloum to help you plan. She’s the best!

P.s. Keep scrolling for the photos…the colors in Italy are eye candy!

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About Emily

A crisp NYC edge, savvy female empowerment, and the earnestness of newfound motherhood are what bridge the gap from trendy to timeless. Hailing from New York and residing in Atlanta. Welcome to Born on Fifth.

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