Creating a guide that captures everything I want to share about our trip to Italy this fall feels almost impossible. After what felt like a transformative experience, I hope this guide lends lots of inspiration to plan a trip of your own in the near future.
Since I hadn’t spent much time in Italy, (I only visited Florence and Rome after high school) I felt like I needed a bit of handholding to find the type of places and experiences we were after—authentic things, off-the-beaten-path, and imbued with traditional Italian flair.
I was lucky enough to connect with Elizabeth De Filippo-Jones, after seeing a trip she helped plan for Julie O’Rourke, of Rudy Jude, to Tuscany last year. It looked like such a dream and I just knew I needed her expertise to help connect me with the right spots.
By way of Milan, Elizabeth offers a unique curated experience that fits your travel needs. A cooking class in a 400-year-old biodynamic estate? She’s got you covered. An 8-course lunch with a world-famous Italian butcher? Yep, she’ll get reservations for that, too. Having someone call restaurants for you made all the difference and assured you’d get into old-school places.
Because Italy can be such a busy destination, depending on the time of year and where you go, I realized how important planning ahead is. Having Elizabeth be our concierge while traveling also gave me peace of mind, which is especially helpful when plans change.
Finding boutique hotels and villas is another one of her specialties along with recommending different areas of town to explore or stay in. There were so many “pinch me” moments and we couldn’t believe just how magical each day was.
Something else I appreciated about working together was the Google Maps guide she sent us for Florence and Rome. So beyond what she already booked for us, she had recommendations for a few different areas and it really came in handy.
Especially since social media is so packed with “best of” recommendations having someone who follows those trends and actually lives in Italy is so useful!
Now, mind you, I love to research and find incredible places when I travel but with Elizabeth’s guidance, it made that process a lot more streamlined and took the guesswork out of where to start.
All this to say, I’m so glad I sought support for this trip because it really made all the difference and made for such an unforgettable time. I can’t wait for her to plan a future trip for us to Puglia!
If you want someone who finds the best guides with personal relationships and first-hand knowledge, Elizabeth has you covered.
Lucky for you she’s offering free 30-minute consultation calls through the end of the year for travel design to help you create highly customized itineraries and bookings based on your personalized travel needs.
So, if you’ve been pining for a trip to Italy and need a gentle nudge to get the ball rolling, consider this your sign to book a consult with her.
Florence
Old world, artisan, and completely walkable, Florence is the kind of city where you can find endless magic just by meandering through its cobblestone streets. Rich with history everywhere you look, it’s easy to imagine what life was like hundreds of years ago.
We stayed in the Oltrarno area and loved how casual and quaint it felt. It’s about a 10-minute walk from the Arno River so you’re not in the thick of the more touristy areas, which we loved. There were plenty of cafes, shops, and restaurants for us to explore just a few steps away, so we didn’t feel like we were missing anything—except the crowds.
Where to stay
Numa | We stayed in a rental a stone’s throw from Palazzo Pitti, a Medici palace with incredible gardens and a city view. If you’re traveling with a group, this spot is very comfortable, with full bathrooms in every room, a spacious living room, and a mini kitchen. It was simple and clean but missing some of the amenities and charm of boutique hotels in the same neighborhood.
Ottantotto Firenze | Also in the Oltrarno, this chic and cozy boutique hotel, once a noble residence, has just seven rooms. I’d love to stay here next time we visit since it also has a lovely garden that makes you feel even more at home in the heart of the city.
Hotel Palazzo Guadagni | A bit more grand, this hotel dates back to 1505 and has a rooftop bar! The rooms are spacious and bright, rich with old-world Florentine charm.
Antica Torre di Via Tornabuoni 1 | Tucked inside a medieval tower, this boutique hotel is located on the esteemed street of Via de Tornabuoni. The rooms feel timeless, with luxurious details and royal textiles.
What to see
Uffizi | An incredibly stunning gallery, the Uffizi is home to the greats, from Botticelli, Mantegna, and Correggio to Leonardo, Raffaello, and Michelangelo. Not to mention standing in front of “The Birth of Venus” was a highlight of our trip that I will relish for years to come. Book tickets in advance for a specific time slot, so you can skip the bigger lines and spend more time enjoying all of the art.
Santa Maria del Fiore | Right next to the Uffizi, you can’t miss the intricate facade of one of the largest cathedrals in the world. Admission is free, but everyone wants in, so plan accordingly, like everything else in this city.
Galleria dell’Accademia | Most known for displaying the David and a rich collection of early Italian paintings, it’s another important gallery to spend an afternoon enjoying the best of Italian art.
Palazzo Pitti and Boboli Gardens | Just at the foot of the Boboli hill beyond the Arno River, this Medici palace showcases the wealth and power of this well-known royal Tuscan family. Make sure to meander in the gardens while catching an incredible birds-eye view of the city.
Where to eat
Il Santo Bevitore | We made a reservation here for our first night in town, and we’re glad we did because it was busy! Set in a cozy brick tavern complete with an old-school bar and floor-to-ceiling wine shelves, you’ll enjoy refined Tuscan dishes by candlelight. Start with the antipasto and order a few kinds of pasta and a main dish to share. It was the perfect meal to start our time in Florence.
Trattoria Sostanza | Word to the wise: you’ll need reservations to get into most spots for dinner, especially one as good as this, so plan ahead. However, we were lucky enough to make it there right when they opened for lunch and got a table. Tiny enough to see the kitchen from every table, it’s an unfussy cozy spot covered in tile with old photos on the wall. From the owner to the chefs, everyone made us feel right at home and the food did not disappoint. Their house pasta, famous butter chicken, egg and artichoke pie, creamy white beans, and chicory salad hit the spot and didn’t leave much room for dinner.
Trattoria Cammillo | After a long morning of galleries and wandering around the city, we caught the last table for lunch at Cammillo. Seated below arched brick ceilings with white tablecloths, this is another cozy spot that’s worth the hype. I ordered a glass of the best Rosato I’ve ever had, the crispiest fried zucchini flowers, and tortellini in Brodo, but there’s so much on the menu to try and share.
Caffé degli Artigiani | This was our morning cappuccino and cornetto spot where we watched the tiny birds fly down from the roofs to get their breakfast, too. Just about a 3-minute walk from our rental, it always felt like such to get a glimpse of the city before most people were out and about.
All’Antico Vinaio | Schiacciata sandwiches were one of my favorite things to eat in Florence. Light, airy, and foccacia-like, I just couldn’t get enough of that perfect bread. While there are plenty of sandwich shops, with All’Antico Vinaio being the most famous, I Fratellini is another worth checking out.
Vivoli | If you’re in the mood to be a total tourist, wait in line for the most delicious and utterly rich affogato. The pistachio version was pretty popular, too!
Where to shop
Santa Maria Novella | Originally founded by Dominican friars in 1221, where they cultivated herb gardens for preparations such as ointments and balms, it’s considered to be the oldest pharmacy in the world. Plan on visiting the San Niccolò-devoted chapel, which is now their boutique museum, where you can experience their full line of perfume products and stock up on some treats to take home with you.
Il Bisonte | We stumbled upon this shop after spending the afternoon in a marble paper workshop—yes, Elizabeth can book this for you, too! Il Bisanti is an iconic Florentine leather brand that’s been around since the 70’s. All I can say is the quality is 10/10 and there are so many timeless colors and products to choose from. I picked up a small cosmetic bag and have been eyeing a few things to grow my collection from them.
Epoca Vintage | The vintage shopping in Florence is really good, so if you’re into finding some treasures, plan to pop into a few shops. Epoca was an organized shop that curated some lovely jackets and leather pieces. Wish I could have spent more time in here!
Pegna dal 1860 | Who doesn’t love a gourmet grocery store, especially one that was a monastery from the 1600s? You’ll find lots of beautifully packaged goods to take home with you here.
I can’t wait to share part two of our time in Italy in the coming weeks. This post would have been way too long had I tried to include the Tuscan countryside AND Rome. So, if you were looking forward to those, stay tuned!
Ciao! - Sarah Kate
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