Flights to Italy Have Never Been Cheaper—Here's How to Plan Your Trip

Updated 07/19/17

If there's one destination that's giving us serious vacation envy at the moment, it's Italy. It seems like everyone on our Instagram feed is soaking up the Sicilian sun, lounging under the orange umbrellas in Positano, or riding gondolas in Venice. Given the recent flight deals to Rome, it's understandable—it has never been more affordable to jet to this European gem.

If you're among the lucky ones who scored a flight deal or can't take watching everyone else's travel shots of Italy and are planning to go yourself, we've mapped out the hard part for you. Ahead are three very different itineraries that cater to your travel style. Foodies will savor every bite of prosciutto and parmesan in Bologna and Parma while sunseekers can't miss the Amalfi Coast. Oh, and first-timers need to make their way from Rome to Florence and Venice.

You can close your Google Maps browser—this is exactly where you should go in Italy.

The First-Timer

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Rome

Multiple budget airlines have been offering discounted fares to Italy, and the vast majority fly into Rome, the capital. If this is your first time to Italy, dedicate at least two full days to being here. Rome is a bustling city steeped in history, but it often polarizes travelers. In summer, the humidity can reach an uncomfortable high, which is only made worse by swarms of tourist groups, so time your visit accordingly.

If you do choose to visit in the middle of summer, wake up early to see the major attractions, before the temperature soars. One of the little-known ways to skip the queues is with a ticket to Palentine Hill, an ancient site in the heart of the city. The ticket includes entry to three major attractions—the Colosseum, Roman Forum, and Palatine Hill—and is valid for two days. On the second day, arrive at the Colosseum when it opens; the majority of the people in line are forced to wait for tickets, giving you a coveted moment to take in the towering structure in silence.

Florence

After spending a few days in Rome, venture north to Florence, the jewel of Italy's Tuscany region. The journey takes just two hours by train or three hours by car. If you only have one mission in Florence, it should be to scale as many towers as possible and view the city from above; hundreds of terra-cotta tile roofs create a sea of burnt orange. Add the Duomo to your list of things to do—it's one of the best vantage points to see the city.

Venice

Sure, it's a little far from Florence, but if it's your first time in Italy, then Venice should absolutely be on your itinerary. Skip the train and book a flight to arrive in just two hours. When you touch down, drop your bags at boutique hotel Corte di Gabriela hotel and venture into the heart of Venice to wander the canals. Head to Piazza San Marco and the Rialto Bridge, and climb the tower at San Giorgio Maggiore for one of the best views of the city. Order a bellini at Harry's Dolci before hailing a gondola to see the beautiful crumbling buildings from the canals.

Original Illustration by Stephanie DeAngelis
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The Sunseeker

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Naples

Some travelers love Naples for its excellent pizza and energetic pace while others find the city overwhelming. If you do choose to spend time here, be sure to stop by L'Antica Pizzeria da Michele, the famous pizza store Julia Roberts visited in Eat Pray Love. Celebrity hype aside, the family-run pizzeria serves an incredible slice of margherita.

Capri

Jump on the fast ferry to reach Capri in less than an hour—this is where your summer vacation begins. Known as one of the most beautiful, exclusive islands and beloved by celebrities and European royalty alike, Capri delivers classic Italian glamor in spades. Head straight to Da Giorgio, a seafood restaurant just steps from the main square, for pizza and people-watching.

Capri is famous for its azure grottos, many of which are only accessible by boat. Book a private tour and spend a day exploring the grottos, then end your day with a romantic dinner at Terrazza Brunella, which has incredible panoramic views.

Sorrento

Make your way back to mainland Italy and spend a day or two in Sorrento. The town is perched atop cliffs, which make for a dramatic entrance by boat from Capri. If you only eat one meal in Sorrento, it should be at Soul & Fish. The gorgeous waterfront restaurant serves excellent fresh seafood with a complimentary glass of prosecco. What more could you ask for?

Positano

Make your way down the Amalfi Coast to Positano, one of the most photogenic villages in the region. You'll need at least three days here to fully appreciate the beauty of this hot spot. Reserve a sun lounger on the main beach and take a dip in the piercing blue water to see the sorbet-colored cliffside from the sea. Then, make a reservation at Le Sirenuse, a stunning vine-covered restaurant with unbeatable views. If you've got time at the end of your trip, venture to Ravello, a charming resort town farther down the coast.

Original Illustration by Stephanie DeAngelis
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The Foodie

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Original Illustration by Stephanie DeAngelis

Bologna

It's no secret that Italy is a food and wine lover's paradise, but a few towns should be at the top of your list if you're serious about sampling the best. Start your trip in Bologna, home of the traditional bolognese, ragu. Locals rave about All'Osteria Bottega, a modest, authentic Italian restaurant with a menu that "features the best hams from the region," according to the Michelin Guide. A few other eateries to add to your culinary bucket list include Serghei, Spacca Napoli, and La Sorbetteria Castiglione for one of the best gelatos in town.

Modena

Next up: the home of balsamic vinegar, Modena. The rich syrupy elixir is like gold in this town—trust us when we say it's nothing like the variety you find in your local supermarket. Be sure to visit a traditional vinegar house to see how they create the best vinegar in Italy.

Foodies should reserve a table at Osteria Francescana, which was crowned the best restaurant in the world in 2016. The three-star Michelin-rated gem is nestled down a cobbled street in Modena and has been credited for "reinventing Italian cuisine."

Parma

Just an hour's drive from Modena is Parma, the home of Parmigiano Reggiano and Prosciutto di Parma. Here, you can find traditional cheese factories and world-class restaurants—there's certainly no shortage of charcuterie platters. Nibble on strawberry risotto or pears poached in wine at La Greppia, then savor a glass of vino at relaxed trattoria Enoteca Fontana.

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Have you been to Italy? Share your itinerary and travel tips with us below. 

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