CITY GUIDE: Where to Eat, Play, Explore & Shop in FLORENCE

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CITY GUIDE: Where to Eat, Play, Explore & Shop in FLORENCE

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Aisha Hillary shares her love for the city of Florence and her top tips on where to eat, play, explore and shop…

I can’t believe it’s been three years since my first visit to Florence when the city stole my heart. Since initially living there for three months over the winter, I have been back three times, each time returning to favourite haunts and discovering some new places and experiences. Here’s my guide to Florence with the hope that more people wil fall in love with this gorgeous, fairytale city.

The City of Florence

Florence, founded by Julius Ceasar, was the birthplace of Leonardo da Vinci, home to some of the worlds most valuable art and where the piano was invented. Florence is rich in renaissance history, creativity and inspiration, all you need to do is take a walk around and admire the architecture and art history around any corner. I also love that it is reasonably small so you can explore every gorgeous corner of it. Weather in Florence and Tuscany is generally pretty mild but Florence’s location in a valley makes temperatures vary from other areas in Tuscany.

The warmest months are generally July and August, with a little breeze it does make the city quite unbearable if you don’t like getting your sweat on. June and September are both really lovely and warm without it being too hot. In August many Italians escape the heat of the city and outside of the historical centre, a large number of local shops and restaurants close down for almost the entire month as they go on vacation. This tradition is slowly changing and most shops in the centre will be open in August however something to keep in mind if you want to get local with the locals. The coolest months are December and January when I was there, so make sure to dress in layers!

So the best time to visit Florence, although it is the busiest with tourist and most expensive in May, June and September, to enjoy the art and music festivals, open-air dining and all the kind of Italian lifestyle you dream of experiencing.

What I suggest to shake off the jet-lag, is to take a run along the river and up to the Piazzale Michelangelo lookout, as this gives you a great perspective of where everything is and the size of this wonderful city. You also can run back across the historic Ponte Vecchio to see all the traditional jewellery shops in this little mall over the Arno and then you really know you have arrived in Florence.

Where my story begins….

I was introduced to a phenomenal woman called Nicole Still, founder and #trailblazer at VIAJIYU, Italy. I was connected to her via a mutual friend who said she had an amazingly generous and big heart. When we spoke over the phone (she is based in Florence) she suggested I do a residency at VIAJIYU, offering her home and office space (@ Piazza Santa Trinita) while she was doing her annual trunk tour around America.

So at the end of 2016, I packed up my bags and I went on a three-month adventure to Florence. Reflecting on my time there, it was such an amazing experience, inspirational, showed me the gift of giving and being kind, as the VIAJIYU team opened their arms, home and beautiful shop in Florence to me.

VIAJIYU hand made flat shoes. Made in Italy. Made to order.

Before I start I have to give you a little insight into “VIAIJYU”, VIA (vee-uh) Italian for “road”, JIYU (zhoo) Japanese for “freedom” meaning “The Freedom Road.”

The brand is handmade, made to order, quality, unique and absolutely timeless shoes. She has a colourful past as a journalist, has run multiple businesses however her journey has led her to Florence, where she and her partner Sam, make people happy one foot at a time. She has this innate kindness to give, inspire and teach and runs a program for “TRAILBLAZERS” to empower aspiring female entrepreneurs and students #VYT #TRAILBLAZERS by giving them a platform to connect, space to work, and to improve and expand their skillset. Often these women are invited to design a pair of shoes for others to enjoy and experience time getting inspired in their boutique in Florence.

My time in Florence and working with the team at VIAJIYU has inspired me in so many ways, and now, beyond my bespoke crafting offering into a new direction called ‘Styled By You’ for Hills & West. This is launch in August this year so keep an eye out :).

I also designed my men’s collection while I was in Florence and have been refining it since I have been back… and we are so close and looking at an August reveal. Lots of things happening in August!

It may have taken me a while to share my favourite spots however I know you will love my EAT, PLAY, EXPLORE and SHOP version of FLORENCE.


Initially, I stayed at Nicole’s home in Piazza De Nerli in San Frediano, on the other side of the river from the old town, with so many delicious places to eat, I highly recommend the area. When I went back I stayed in both the old town for a new experience and went back across the river in an Airbnb, to continue my experience as a local.

One apartment was located near Duomo, S.M. Novella central station and all the main museums in the centre, you will love for its bright, spacious and quiet space, with a serene atmosphere emphasized by a north European style, furnished with attention to details.

Also check out our wonderful architectural loft in my old hood, “Loft Ventuno In stile contemporaneo unico nel suo genere

There are soo many amazing choices with phenomenal style and architecture, just browsing through the homes available is a treat.

This rooftop apartment also looks amazing however it was booked every time I went. Next time.


The Capital of the Tuscan region of Italy, Florence serves up wonderfully authentic food paired with delicious wines.

Especially for breakfast…

La Menagerie: My favourite cafe for breakfast is this gorgeous stunning space delivering everything you want, from healthy meals to cheeky fresh pastries, gifts and flowers. Is also a gorgeous cocktail bar after hours.

Cantinetta dei Verrazzano: Love love love this little gem and spent many hours having my macchiatos and nibbling on their pastries. Wonderful place to just watch the locals come in and pick up something for breakfast on their way to work.

For any time of day…

One of my favourite group of restaurants, is S. formo, Iil Santo Bevitore and il Santion Gastronomia.

Il Santino Gastronomia: you can just hang in this little hole in the wall all day casually drinking wine and snacking on the complimentary bread with cheese and delicious meats. The bread was even baked in house and if you are after some cracking wine, ask the waitress for their recommendation of your preference! It’s a great little authentic gem.

Their more upmarket restaurant, il Santo Bevitore, is a definite treat. Book to avoid disappointment. The atmosphere is amazing and the pasta just melts in your mouth. My mouth is watering just thinking about it.


Il Borro Tuscan Bistro: Bases itself around the idea that every moment deserves a special feeling. This restaurant places itself between innovation and tradition. The pasta is amazing, the presentation simple and authentic… I say unforgettable.

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Gurdulu ristorante: In a corner in the Santo Spirito district it protects itself from the flow of tourists and maintains its Florentine essence. Unique, so totally different, this is a one for the foodies who like to try something that will surprise you.


Ristorante Cafaggi: Family-owned restaurant within Florence, which serves up true Tuscan cuisine. Authentic and such a great place to people watch how the locals interact.


Spumantino al Ponte Vecchio: Facing onto the Ponte Vecchio bridge the Spumantino wine bar. Spumantino offers a journey through new flavours and high-quality food pairings in a refined and elegant lounge atmosphere. Go here at aperitivo time, literally my favourite time of day, to sit, drink and eat nibbles while you catch up on the day’s happenings.


La Cantinetta: Cantinetta focuses on Chianti and its specialities. Owned by the family who runs the Castello di Verrazzano in Chianti they run a speciality restaurant, which produces traditional Tuscan meals paired with their famous Chianti wine.

Mangiafoco: Looking for delicious spritzes and authentic Italian nibbles, Yes all you can eat Salami, truffle and cheese!! My favourite place for a catch-up and bite to eat with a friend. It’s where all the locals hang, so keep an eye out for what they choose, after all they know what’s best!

Ditta artigianale : Perfect little hole in the wall from breakfast, lunch or dinner. This is a 50’s retro place with Scandinavian 70’s wallpaper, very quirky and a cosy little cocktail bar by night. Must try their bagels too!

Fishing lab : For all, you sushi and seafood lovers, is the Fish Lab providing a contemporary twist that will blow you away. The traditional architecture is still in tack as well, with beautiful renaissance arches and ceiling painting. Highly recommend!

Cabiria: A cute little lounge bar if you after affordable drinks and cheeky spritz at the end of a busy day.

Restaurant Buca Mario: Who doesn’t love authentic Italian! This resultant was one of my favourites when I was there, offering a Italian, Mediterranean, Tuscan, Central-Italian, a little on the pricy side but well worth is for a special occasion. Must try their pasta and desserts, permission granted to go all out!!!

Passaguai: Passagaui means ‘no worries’ so sit outside, enjoy the fresh delicious food and watch the nightlife roll past.

Piazza Santo Spirito: Looking for a casual drink with the locals, then this is the square for you. This unique Florentine piazza is the centre of the artisan quarter. Dominated by the last masterpiece of Brunelleschi, the Basilica of Santo Spirito, the square is home to little local markets and antique fairs. Tip, head at aperitivo time and you can get your fill of delicious snacks too.

Rooftop bars…

Grand Hotel Cavour rooftop: One of my favourite rooftops (because every evening should be on a different rooftop in my opinion), enjoy the sunset and a smokey old fashioned, with some laidback tunes, in a magical location to watch the sun go down and watch all the grand cathedrals all light up below. There is no signage so walk right through the lobby to the lifts at the back and take the lift to the top.

There is also a ‘Secret Bar’ underground bar, in the domed cellars, for a cheeky nightcap on the way out.

Lucchesi: The Plaza Hotel rooftop has a pool the lounges that open to the public after 7 pm, so get in quick after a long day walking around the city and dip your feet in to relax!

SE·STO on Arno: Iconic Westin Excelsior rooftop bar in the heart of Florence giving you a 360 view of the whole city from above. This Mediterranean restaurant has unique settings paired with a classic contemporary execution to create an unforgettable experience. I highly recommend for a special dinner occasion, or pop up there for a spritz and sit by the window to soak up the views.

La Terrazza Continentale: Watch the sun go down and let the view overlooking the river make you want to pinch yourself! Very warm atmosphere, the perfect place to end a busy day.


FLO Club Piazzale Michelangelo: We love a good nightlife and a classy cocktail bar. The flow will guarantee a good time for you and your gals or even a date night! With gorgeous outside lounges and great music!

Belvedere Monument: A truly spectacular view from above! This iconic spot is up on a hill and provides the views of Florences city. It was built in 1869 and designed by architect Giuseppe Poggi on a hill just south of the historic centre, during the redevelopment of the left bank of the Arno. Definitely, have to venture to!

Piazzale Michelangelo: A beautiful square with a panoramic view of Florence city, located in the Oltrarno district on top of the hill. You can also walk through nice gardens to get to the top and along the river to get there, a gorgeous way to spend an afternoon. Even grab some drinks, have a picnic and nibbles and watch the sunset.

Italian Cooking Classes: Try something different and really get into the culture I did a fabulous cooking class making authentic Pizza and Gelato! It’s a great way to experience all the traditions of making Italian food and a hands-on way to learn about their kitchen environment. Was definitely educational and also a very playful activity with plenty of giggles and of course the best part at the end when you get to eat it and enjoy some complimentary wine.

Explore and get seep in the history of Florences amazing cathedrals and churches. Here is a list of the top 14, however you can’t miss them as you wander the streets, each has its own story and is filled with architectural and artistic wonderment.

Food Markets

The Mercato Centrale, or Mercato di San Lorenzo are two local markets right next to each other in Florence with loads of yummy fresh food downstairs but loads of casual stalls upstairs. You can go with your group and eat different food and then sit at the wine bar and select different local wines. I recommend not having breakfast and just jump around the markets all day and try a little bit of everything, but no need to feel guilty because you’ll walk it off when you go rooftop hopping that night (I recommend Panicale area, after all, it’s along the way hehe)

Ponte Vecchio Bridge:

Walk along the Fiume Arno to escape the city centre and admire the sights while moving. Running past the famous Ponte Vecchio Bridge and one of my favourites. The Ponte Vecchio is a medieval stone closed-spandrel segmental arch bridge over the Arno River, I always wonder how the bridge stays up with all that weight on top of it.

Cinema Odeon Firenze: Get engrossed by the history and culture and head to this old historic theatre, still screening classic movies. Since the beginning of the 20th century, all the best films and important events took place on this stage in the old town hall. Famous guests from all around the world visited and enjoyed all that the Cinema Odeon has to offer. Gorgeous original architecture as well definitely need to take some photos! So sit back, have some popcorn and a drink and enjoy a low-key carefree movie night.


Gucci Museum: One of my favourite places to revive and find more inspiration for styling was at the Gucci museum. Truly gorgeous pieces from the original collection of Gucci and I always find it fascinating seeing the evolution of the brand and how they are inspirational in all aspects of design, not just clothing and accessories. Definitely worth visiting!

Palazzo Strozzi: On the palazzo’s Piano Nobile and the Strozzina area the Fondazione organises art exhibitions ranging from the art of the ancient world via the Renaissance to the modern and contemporary era. The Fondazione also hosts a permanent exhibition on the history of the Palazzo Strozzi, a café and a museum shop on the ground floor, giving onto the palazzo’s Renaissance courtyard where it organises concerts, performance art, installations of contemporary art, theatrical performances and a great deal more. There is always something for everyone.

When I was there I saw the Ai Weiwei- LIBERO exhibition, who was the first artist to exhibit across the entirety of the Palazzo Strozzi spaces, celebrating the world’s most influential contemporary artists who challenge the political views of around the world. If you can see his work anywhere around the world I would highly recommend as his art continues to push boundaries!

Galleria dell’Accademia: Of course there are plenty of galleries in Florence to pick from, so I highly recommend the best if you are to visit one and that, of course, the Galleria dell’Accademia. Filled this all the original sculptures and paintings of Italy. Of course, though it’s a no brainer to book your tickets online or even if you want to make the most of it and book a tour, they are truly interesting if you enjoy your art history.


Hidden Forest Markets: I’m a huge fan of unique styles and quality wears, so I promise you in this beautiful store you’re sure to walk away with something gorgeous. Full of quality locally made pieces you’ll fall in love with. I still wear my little gems and they still draw so many compliments!

Vintage Selection 29: For all you stylists and fashion gurus, the Running Vintage Selection 29 is a ‘fair-cum-creative/stylistic laboratory that offers a place for the big names in international fashion to meet with their buyers and fashion designers’. Plenty of one of a kind handcrafted outfits, super stylish.

More Time to Adventure

If you have time I always advise people to venture out of the city of Florence.

The last tip, as they say, ‘when in Rome’, you have to make sure you experience ‘Aperitivo time’, the Italian version of happy hour with delicious treats.

An aperitivo is a pre-meal drink, accompanied by small snacks, specifically meant to wet your appetite. The concept of the modern apéritif is generally thought to have been invented (or effectively marketed) by the distiller Antonio Benedetto Carpano, who also created one of the first types of vermouth in Turin in 1786. He claimed that his special combination of fortified white wine and various herbs and spices stimulated the appetite and were more suitable for ladies to drink than red wine, making it one of the first aperitivo drinks. I am in total support of nibbles with you pre-meal drink, and its a great way to taste the many Italian delicacies without breaking the bank.

There are so many more things to share and do in Florence, I can’t recommend it as a destination enough. I do hope my tips on EAT, STAY, PLAY and SHOP have inspired you to visit. I am so grateful for the opportunity I had with VIAJIYU as Florence, and the experience, really shaped where I am today and made me persevere with my dream to create beautiful bags for Hills & West.

Always take those leaps of faith because they are always worth it!

For more, read Aisha’s City Guide to Los Angeles and her City Guide to Johannesburg

Aisha Hillary
Born in Australia and raised by Dutch parents who ran an international publishing business, experiencing the world, its different cultures and documenting it along the way, was in Aisha’s blood. After 15 years of travelling as a communications professional in retail, media, food, film, entertainment and tech, living in both the UK and Australia, it was time to create Hills & West. In 2015 Aisha left her corporate career and travelled to 50 destinations in 105 days carting a self designed backpack prototype. The Morgan Collection was born and now she collaborates with local artisans, designing bags and sharing the stories of the people and places that inspire her. From the beginning the Hills & West mission has been simple - do what we love, create exceptional pieces, share stories and make people happy along the way.


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