Wherever you go in Italy, your closest city is guaranteed to be filled with cultural landmarks, fine food, and fascinating history. The best Italian city breaks promise world-class museums by day and aperitivo from a bustling piazza come evening. There are the heavy hitters, of course — how could we forget Rome, Milan or Florence! But some of our firm favourites are the smaller, off-the-radar cities that invite a more laid back approach to sightseeing.
Keep reading to discover our top five Italian cities to explore, with insider tips from our local specialists and the best luxury villas in Italy to enjoy while you’re there!
FLORENCE
Get to the heart of Italy’s Renaissance hub
Best for: art lovers and foodies
Okay, so we couldn’t not start with Florence. There is a reason this UNESCO listed city is number one on everyone's Italian city break checklist. The compact centre is perfect for exploring by foot, crammed full of world-famous Renaissance art, from Michelangelo’s David at the Galleria dell’Accademia to priceless works by Leonardo da Vinci and Botticelli at the Uffizi.
Tick off world-famous sights, like city views from the Duomo’s bell tower, hunt for vintage and
artisan finds in Oltrarno and stumble across the occasional new discovery along the way. To really get beneath the city’s skin these days, you are best off teaming up with a local Florentine. Our concierge can arrange authentic experiences, from a paper marbling workshop with a local artisan to a coffee workshop with a Florentine barista.
Where to eat: Lunch at Trattoria Cammillo is a must — think traditional Tuscan decor with an elegant twist. Be sure to try their celeriac and bottarga salad and the gamberi al curry con riso with homemade chutney.
Head to Sabatino in Porta San Frediano for dinner — the menu changes everyday and is written on a vintage typewriter. You’ll be among locals here, which is all the more reason to stay for your Florentine meat-fix and order the roastbeef.
Insider tip: Start your day with breakfast at Pasticceria Gualtieri near Porta Romana and the Boboli Gardens. Our resident Florentines agree it's the best and there are great options for vegans too.
Where to stay: I Giullari is an elegant villa in an exclusive hamlet where Galileo Galilei once lived. Enjoy peaceful vistas from your private heated pool knowing the iconic views of the city skyline at Piazzale Michelangelo are just a 20-minute walk away.
LUCCA
Slow down in the walled city of 100 churches
Best for: cycling, opera and the great outdoors
Usually a bolt on for visitors to Pisa, Lucca is one of Tuscany’s underrated cities that has so much to offer in its own right. This tiny medieval city is enclosed by a mighty ring of 500-year-old walls and is surrounded by vineyards. Cars are not allowed in the city centre, so you can explore by bike or on foot in peace. The narrow streets and beautiful cobbled squares are lined with palazzos and dozens of Romanesque, Gothic and medieval churches.
The home city of the composer, Puccini, Lucca is a romantic base for opera enthusiasts. Torre del Lago, which hosts the summer Puccini opera festival can be reached in under half an hour, as can Tuscany’s more popular white sandy beaches. And, some of Tuscany’s best kept secret landscapes are right on the doorstep, from the Garfagnana to the Apuan Alps.
Where to eat: Don’t be fooled by the humble exterior at Antica Locanda di Sesto. Sitting on the outskirts of the city at Ponte a Moriano, the inn can trace its origins back to the 14th-century. Try the spaghetti with guanciale creamed in a giant wheel of pecorino cheese, and wood-fired meat for secondo is a must.
Insider tip: Lucca is an exceptional destination for shopping. Many of the stores still display their original historic shop signs, so be sure to pay attention to all the quirky signs you see on your stroll about the city. Excellent for antiques, Lucca holds the second oldest antiques fair in Italy every month.
Where to stay: La Gattaiola is an 18th-century farmhouse bursting with original Tuscan charm, with views of lovely Lucca from the private pool and a spacious loggia for alfresco living. Nestled in the hills just 3 miles south of Lucca, La Gattaiola is perfect for those wishing to stretch out their city break with hiking in the countryside and lazy villa days.
VENICE
Find pockets of calm in the floating city
Best for: endless romance and island-hopping quiet
Venice gets a bad rap for the constant influx of tourists, but of course it's still on everyone’s list of spectacular, bucket-list city breaks. We’re sentimental about Venice. Beyond the obvious landmarks — St Mark’s Square, the Doge’s Palace, the Rialto Bridge, even an overrated gondola ride — is a quiet, thriving city waiting to be discovered on a local level.
Enjoy a quiet stroll through Dorsoduro and savour a campari spritz on the Zattere, head out to the island of Torcello and explore the Byzantine church — even San Giorgio Maggiore is quiet in the fall.
The city is rammed full of incredible museums and churches: you’ll want the Accademia for the Venetian greats, Palazzo Fortuny for something sumptuous and unconventional and the Scuola Grande di San Rocco for a slice of Venice’s historic pomp. We could go on: just read here for our favourite churches and here for our favourite museums.
Where to eat: Il Paradiso Perduto for authentic Venetian cuisine; order the fresh catch of the day served with polenta and sometimes a smattering of live jazz. Al Covo is also great for seasonal menus and Al Timon for unbelievable steak washed down with a local Valpolicella.
Insider tip: Not strictly insider knowledge, but you won’t regret a wine tasting and tour at Venissa; this special place is reviving the once-believed extinct Dorona grape and their wines have an exquisite saline finish you won’t find anywhere else. If you are staying in one of our luxury villas near Venice, they can arrange for a private boat to collect you from St Lucia train station. Mazzorbo is one of the few quiet, local islands still left in Venice as well.
Where to stay: Villa Michiel is an elegant 17th-century Venetian villa just a 20-minute drive to Piazzale Roma, where you can catch a boat or walk into Venice. There is no need for a car, you can walk into the small town of Mirano for local shops and restaurants and you have an international airport on the doorstep. Prolong your weekend break by your private pool and plan day trips filled with Palladian Villas, Prosecco wine tastings, walking and golf in the Colli Euganei hills.
ORVIETO
Visit some of the most beautiful places in Italy
Best for: White wine, incredible views and the ‘Golden Lily’ of Cathedrals
Orvieto is one of those places that will take your breath away from the moment you lay eyes on it. Resting on a dramatic turret of volcanic rock, the tightly packed city towers above the Tiber Valley. It may be one of Umbria’s better known cities, but it still has a homely lived in feel. Dating back to the Etruscans, there is plenty of history to uncover here, between medieval streets, majolica-style ceramics, Renaissance wells and frescoed chapels.
Of course, you cannot miss Orvieto’s pink marble and gilt mosaiced cathedral which crowns the city skyline and is one of the most beautiful churches in Italy. For the best views climb to the top of the 1313 Torre del Moro, but to really get beneath the surface of the city, you’ll have to delve deep underground. Orvieto is built on a fascinating network of tunnels and caves, which adapted over the centuries into artisan kilns, olive presses and escape routes for wealthy nobles.
Where to eat: Coro on Via Duomo is so good it deserves a Michelin-star. The bistro and accompanying cocktail bar, Gocce, both follow a seasonal menu. They are situated in a deconsecrated church, with high ceilings, mood lighting and decor as divine as the food.
Insider tip: Head out of town towards Lake Bolsena to Trattoria del Conte, a simple roadside restaurant that is always packed with locals serving traditional Umbrian dishes.
Surrounding the city are vast swathes of vineyards dedicated to Italy’s iconic white wine. Decugnano di Barbi is a stunning winery to the east of Orvieto that has been producing wine since the 13th-century. The current custodians produced their first bottle of Orvieto Classico in 1973, alongside a superb range of white, red and rose wines.
Where to stay: Elevate your city break in Italy at Villa Clara, a fully-staffed, high-level luxury escape with the most incredible views of Orvieto. Just 15 minutes from the city, you can balance the peace of Umbria’s stunning countryside with trips into Orvieto for dinner. Whether you are relaxing in the dining room, out on the terrace or by your private pool, relish your own private view of Orvieto cathedral.
PERUGIA
Experience the buzz of Umbria’s most cosmopolitan city
Best for: indulging your sweet tooth and exquisite Jazz
Much like wider Umbria, Perugia is one of Italy’s most frequently overlooked destinations. There is plenty more to the city than the annual Umbria Jazz and Chocolate festivals, although they are well worth making the trip to experience. Perugia is home to one of Italy’s oldest universities, which balances the Etruscan history and medieval piazzas with a youthful vitality. For foodies, this also means an excellent choice of bars and cafes.
Most of Perugia’s key sights are centred around the picturesque Piazza IV Novembre, home to the cathedral and the National Gallery of Umbria. The art gallery is housed in a fascinating 13th-century gothic palace and can count works by Fra Angelico, Perugino and Piero della Francesco among its collection. You’ll also want to pay a visit to the Tempio di Sant’Angelo. The 5th-century romanesque church was built on top of the ruins of a Roman temple and is one of the most interesting buildings in Perugia.
Of course, Perugia is also best known for the Perugina Chocolate Factory behind the iconic Baci Perugina. Have our concierge arrange a tour, tasting and lunch with a local guide!
Where to eat: Osteria a Priori sits right in the centre of historic Perugia and serves an all-Umbria menu that spotlights small artisanal producers from the local area. Start with legumes from Lake Trasimeno and seasonal black truffles. Handmade pasta dishes include Chianina beef ragu and pecorino from Norcia, while second courses are warm and hearty whether you love meat or are a vegetarian.
Insider tip: To satisfy your sweet tooth, head to the Cioccolateria, Augusta Perusia for artisan chocolate and gelato that is off the main tourist trail. The local chocolatier first opened shop in 2000 and creates exquisite Baci and pralines.
Where to stay: We bet you didn’t think a city break to Perugia could include a fully-staffed, 17th-century villa set in a 10-acre park with classical gardens, an avenue of trees and a private swimming pool. Torre Della Duchessa offers all this just 4 miles from the centre of Perugia and you can walk into pretty Pila for bars, shops and restaurants as well.
Let’s make plans together!
At Tuscany Now & More, we like to do Italian city breaks a little bit differently. Why settle for a whistle-stop weekend city break, when you can relish an unhurried, leisurely getaway?
Our luxury villa rentals bring Italy’s greatest cities to your doorstep without having to compromise on space or exclusivity. Enjoy peace of mind knowing privacy, panoramic views and post day-trip dips in your private pool await you when you return to your luxury villa in Italy.