Your Guide to Spending Two Weeks in Italy

Holiday in paradise? Check. Perfect itinerary to match? Double-check. This is how to spend two weeks in bella Italia!

Updated in May 2022

There are few places in the world as enchanting and enduring as Italy. From world-class cuisine to the ever-present influence of Renaissance-era culture, it’s no mystery as to how Italy continually dominates the tourism industry. And while it’s true that you could spend an entire lifetime exploring the cobblestone streets and rolling green hills of this stunning European destination, most travellers only have two weeks at a time to get their Italian cultural fix. So, how do you make the most out of only two weeks?

With help from our friends at Insight Vacations, we’ve created the ideal itinerary that will tell you how to spend two satisfying weeks in Italy. Let’s get started!

Where should I start in Italy?

As any veteran traveller will tell you, starting and ending in the same city is typically a great way to save money on long-distance flights. But if you’ve only got around 14 days to enjoy your vacation, then consider beginning your trip in one famous city (and major transit hub) then ending in another. This will ensure you won’t be sacrificing precious sightseeing time rushing hundreds of kilometres to get back to your departure point.

That’s why we suggest starting your adventure in Rome, Italy’s capital and arguably its most famous city. Fly into Rome’s Fiumicino Leonardo da Vinci Airport for closest access to the city centre and if you book a group tour, you can arrange for an airport transfer to deliver you straight to your hotel.

Keep in mind that if you arrive late at night, you’ll need to stay at an airport hotel, sleep in the terminal or be prepared to part with as much as 100 euros to get into the city via taxi. There’s little way around this as the public transit between the city and the airport ends fairly early in the evening. Do your best not to arrive after hours as the money you’ll save on the flight will be spent getting into the city.

Not sure what to pack? Bookmark these seasonal packing lists:

How do I get around Italy?

All across Europe, you’ll benefit from an extensive network of regional train systems, and specifically in Italy, the prices tend to be lower. You will also have the option of choosing between faster yet more expensive trains as opposed to the less direct but more affordable routes. However, Italy’s train system isn’t the most reliable, so don’t be surprised if your train fails to show up to the platform. If you’re in a hurry to reach your next destination, we’d strongly suggest simply hiring a car or joining a tour and allow the experts to arrange comfortable, dependable transportation for you.

A group tour is one of the best ways to explore Italy as you can spend all your mental strength on relaxing and enjoying the sights and experiences that Italy has to offer instead of sorting out train tickets, flights, and private cars. You also won’t need to worry about dragging your overpacked suitcase through busy transit terminals.

Of course, flying from one city to the next is also an option, but not a typical choice for a country the size of Italy.

Which cities in Italy should you visit?

1. Rome

Length of visit: 2 days
Top places to visit: St. Peter’s Basilica, the Colosseum, Trevi Fountain, the Pantheon, Piazza Navona, Giardino degli Aranci, and the Altemps Palace.
Must-do activities: After fighting the crowds in the Vatican City to take in the mandatory sights of the Sistine Chapel, you should snag yourself a gelato and stroll through Giardino Degli Aranci (the Orange Garden) located on Aventine Hill. The park provides truly impressive views of the city and is a wonderful way to spend a quiet afternoon.
What to eat: Traditional Roman cuisine includes carciofi (artichoke) prepared alla romana (Roman-style) or alla giudia (Jewish-style), coda alla vaccinara (protein-rich oxtail) and the classic but delicious spaghetti alla carbonara.

2. Pompeii


Length of visit: Half a day
Top places to visit: The ancient Roman city of Pompeii is the reason you’ll visit this area so the ruins themselves are really the only place to visit in this case. Explore the cobbled streets and observe the eerily preserved villas and temples over the course of several hours. There aren’t many markings or signage around to provide much historical context, so this is where a tour guide or guidebook would definitely come in handy.
Must-do activities: Step into the private homes of the ill-fated city’s residents and spot the traces of Italic and Roman domestic architecture. See the famous Alexander the Great mosaic within the luxurious House of the Faun.

3. Sorrento


Length of visit: 1-2 days
Top places to visit: Piazza Tasso, Piazza Sant’Antonino, Marina Grande, Cloisters of San Francisco, Basilica Di Sant’Antonino and Di Sorrento.
Must-do activities: Any journey to the romantic resort town of Sorrento wouldn’t be complete without a visit to the many small, charming places of worship like the Cathedral Di Sorrento, located just off Corso Italia. The interior is quite magnificent, and you can expect to see high ceilings, dramatic round arches, paintings and a sparkling marble altar dating back to the 11th century.
What to eat: Limoncello, the staple after-dinner digestivo of Italy is actually produced in Sorrento, so there’s no better place to enjoy a chilled serving of the good stuff after an unforgettable dinner of shellfish than this coastal town.

4. Capri

Length of visit: 1-2 days
Top places to visit: Blue Grotto, Piazzetta, Punta Carena lighthouse, Villa San Michele and Certosa di San Giacomo.
Must-do activities: Capri is one of the most cosmopolitan islands in the Mediterranean and it exudes as much glamour and natural beauty as you might imagine. After a delicious and filling breakfast, start your day in Capri by hailing a small boat to the iconic Blue Grotto where you can take in the bright blue glow of this small sea cave. During the afternoon you can take a stroll through Villa San Michele’s, the former home of a Swedish doctor and take in its colourful gardens, priceless archaeological artefacts, and marble statues all draped in vines. If you’re in search for the best views then ride the chairlift to the top of Mount Solaro – you won’t be disappointed.

5. Orvieto

Length of visit: 1 day
Top places to visit: Piazza del Duomo, Cappella Di San Brizio, Centro Storico Orvieto, Pozzo di San Patrizio
Must-do activities: You won’t need more than a day to discover the gems of this small city in the heart of Umbria. Spend a couple hours exploring the city’s underground cave network or climb down the spiral staircase inside the historic well of Pozzo di San Patrizio. Round off your experience with by dining in one of the city’s underground grottos – we promise it’ll make for a very memorable meal.
What to eat: Savour delicious antipasti dishes like prosciutto and olive oil-soaked bruschetta before moving on to truffle pasta and hefty servings of salami.

6. Assisi


Length of visit: Half a day will do
Top places to visit: St. Mary of the Angels Church, Basilica of St. Francis, St. Clare’s Church, Temple of Minerva, Communal Square and the Rocca Maggiore.
Must-do activities: Assisi in itself is a UNESCO World Heritage Site, highly regarded for its medieval architecture and for serving as the birthplace of Saint Francis. Therefore you’d be remiss not to visit the Basilica of Saint Francis, which locals will tell you provides one of the most complete representations of 13th and 14th-century European art. Be sure to treat yourself to a meal at one of the local family-operated ristorantes.

7. Perugia


Length of visit: 1 day
Top places to visit: Collegio del Cambio, Palazzo dei Priori, Fontana Maggiore, Rocca Paolina and the Church of San’t Angelo.
Must-do activities: Arrange a visit to a loom-weaving workshop to see the ancient craft in action in one of the town’s artisanal workshops. Snap a picture in front of the Great Fountain in the town’s magnificent main square and simply stroll around at your own pace to take in the magical Gothic architecture.

8. Chianti


Length of visit: 1 day
Top places to visit: Siena and Radda; a city and medieval town respectively and each have their own charms. Siena is defined by its medieval brick buildings and a 14-century tower called Torre del Mangia, which stands 88 meters tall and provides sweeping views of the city. In Radda, you can walk around the winding medieval walkways, including tunnels that are home to charming restaurants.
Must-do activities: In Siena visit the Church of San Domenico, the Civic Museum, the Public Palace, the Complex of Santa Maria della Scala and the Baptistery. In Radda visit the ghiacciaia granducale (Ice house of the Grand Duke), the Propositura di San Niccolo and Palazzo del Podestà.
What to eat: In both Siena and Radda you should sit down to enjoy traditional regional dishes like wild boar, Cinta Senese and hare.

9. San Gimignano


Length of visit: 1 day
Top places to visit: Palazzo Comunale, Torre Grossa, Collegiate Church of San Gimignano and the Sant’Agostino Church.
Must-do activities: Participate in a tasting from the region’s award-winning ice cream makers whose innovative flavour combinations will leave your mouth watering. Once you fill up on ice cream, hit up the aforementioned sites and then wander around the hills of Tuscany.

10. Florence

Length of visit: 1 day
Top places to visit: Piazza della Signoria, Palazzo Vecchio, Santa Croce Basilica, Florence Cathedral, Galleria dell’Accademia, Florence Baptistery, Boboli Gardens and Villa Badini.
Must-do activities: Consider renting a bicycle and riding along the winding bike paths that go through some of the city’s most unique neighbourhoods. Of course, you will also need to make time to visit the Galleria dell’Accademia to see the famous sculpture, David, in person and then take a walk through San Lorenzo Market to sample the local culinary delights on offer.
What to eat: Don’t leave Florence before you’ve had a bistecca alla fiorentina, an expertly prepared steak cut from the loin that will melt in your mouth just like butter.

11. Lucca


Length of visit: Half a day
Top places to visit: Guinigi Tower, Piazza dell’Anfiteatro, Lucca Cathedral and San Michele in Foro.
Must-do activities: Lucca is known as the city of 100 churches, so it could be difficult to choose which ones to visit with only half a day to explore but we suggest St. Michael’s Church and Lucca Cathedral. Next grab an espresso or aperitif in the city’s Amphitheatre Square, a relic from Roman times. You can also consider simply taking a relaxing stroll along the old city walls where you will enjoy a panoramic perspective of Lucca.

12. Cinque Terre


Length of visit: 1 day
Top places to visit: Footpath Monterosso, Pacro Nazionale Cinque Terre, Sentiero Vernazza a Corniglia, Church of San Francesco.
Must-do activities: Exploring the different neighbourhoods and villages in Cinque Terre is the best way to get to know the area but, if you have the chance, you mustn’t pass up the opportunity to embark on a sunset boat tour. If you’re only passing through, then reside to spending an hour or two relaxing at one of the sandy or rocky beaches that sit along the Italian Riveria.

13. Modena


Length of visit: Half a day
Top places to visit: Torre della Ghirlandina, Modena Cathedral, Ducal Palace of Modena, Museo Casa Enzo Ferrari, Duomo and Casa Museo Luciano Pavarotti.
Must-do activities: If you’re into sports cars then Modena will not disappoint. You can visit the Ferrari Museum in Maranello and experience the story of this classic luxury car for yourself before carrying on to the Piazza Grande, the historic centre of Modena. To end the day, sit down at a cafe and watch the locals pass by in search of the perfect aperitivo.
What to eat: Tortelli is a stuffed pasta typical of the region so don’t miss out. In the evening, open a bottle of lambrusco, a fizzy red wine served chilled.

14. Parma


Length of visit: Half a day
Top places to visit: Palazzo della Pilotta, Parma Cathedral, Baptistery of Parma, Galleria Nazionale di Parma, Piazza Garibaldi and Teatro Farnese.
Must-do activities: Aside from visiting all the typical sites, the must-do activity of Parma is simply…well, eating. Eat parma prosciutto, torta fritta, and tortellini until you simply can’t fit another bite in your mouth.

15. Verona


Length of visit: 1 day
Top places to visit: Arena di Verona, Piazza delle Erbe, Juliet’s Balcony, Teatro Romano, Castelvecchio, Giardino Giusti, Castel St Pietro.
Must-do activities: Walk, walk and walk. Verona is totally manageable to explore solely on foot to make the most out of your 24 hours in one of Italy’s most romantic cities and stroll around the Piazza Bra, or head to Juliet’s House early in the day to avoid crowds. We also suggest climbing to the top of the Torre dei Lamberti to see the spectacular skyline for yourself. If shopping is more your thing than visit Corso Porta Borsari, Verona’s famous shopping street which is also home to marvellous wine bars and classic cafes.

16. Venice


Length of visit: 1 day
Top places to visit: Piazza San Marco, Saint Mark’s Basilica, Doge’s Palace, Burano, Grand Canal, Rialto Bridge, Bridge of Sighs, Giudecca Island
Must-do activities: You might feel pressure to take a gondola ride if you’re going to Venice but there’s plenty of other iconic experiences waiting for you, including riding a far less expensive waterbus to get around the city’s waterways. If you’re thirsty, visit one of the city’s many waterside bars, some perched on the edge of the Grand Canal or tucked away in hidden alleys. You can also opt to observe the art of glassblowing on a visit to a traditional arts centre on Giudecca Island or cruise the islands of the Venetian lagoon over to Burano, famous for its candy-coloured houses.

To serve you with an extra dose of inspiration, you can also watch these enchanting Italian cities in action now:

Are you excited for your trip to Italy? Did we miss a city that absolutely must be included on this list? Tell us in the comments! 

Jackie is a travel-addicted Canadian who currently resides in Vienna, Austria. When she’s not writing travel guides or reading her new favourite book, she’s planning her next weekend getaway somewhere in Europe.

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