Best friends laughing with Italy village in the background.

A Besties’ Guide to the Ultimate Italian Vacation

Bond with Friends and Family Over Jaw-Dropping Coastlines, Gelato and More!


Imagine traveling across Italy with your bestie, seeing famous art in Florence, devouring pizza in Naples and museum-hopping in Rome. You might be thinking this sounds too good to be true. Can it all be done on one trip? Essentially the keystone of Western civilization—from religious icons of the Roman Empire to globally influential art, celebrated high-fashion, acclaimed gastronomy, and more UNESCO World Heritage Sites than any other country on earth—Italy is culturally giant. Geographically, however, it’s surprisingly small—only three-quarters the size of California. And thanks to the country’s hyper-efficient mass-transit system, it’s easy to visit both must-see sites of the north and off-beat wonders of the south on a single vacation. Reaching speeds of over 220 mph, Italy’s high-speed Trenitalia trains can shorten travel times by as much as half, compared to driving. This means more time for bonding with your bestie over breathtaking coastal views, shopping until you drop, and consuming enough gelato to sustain a small family.

Women eating gelato in Italy.
Ultimate Italian Vacation - Don't miss out bonding with your besties while eating delicious gelato in Italy.

Go Shopping in Milan

A primary airport hub and a must-see destination in its own right, the chic cosmopolitan city of Milan is the perfect place to start your Italian adventure. From the intricate Gothic style of the Duomo di Milano to the legendary works of Leonardo da Vinci, Milan boasts an abundance of art and architecture at every turn. Castles, plazas, galleries and even cemeteries are dripping in sophisticated Italian aesthetic. In the country’s fashion capital, it’s easy to find a slice of this signature Italian design to bring home. Head to Galleria Vittorio Emanuele II—Italy’s oldest shopping mall and an architectural icon. Two glass-vaulted arcades meet at a central, octagonal glass dome. Inside are the haute couture shops of Italy’s most celebrated designers. Name any luxury label you can think of and chances are, it’s Italian. Prada, Gucci, Dolce & Gabbana, Armani, Versace, Fendi, Valentino—we could go on and on. Italy’s role as a global fashion powerhouse cannot be overstated. Whether you’re looking to find your own shiny treasure or to simply soak up the scene, this is the place. 

Couple with shopping bags walking in Italy
MILAN -  Don't leave Milan without going haute couture shopping at the Galleria Vittorio Emanuele II, Italy's oldest shopping mall.

Savor Foodie Finds in Bologna

The next stop on your Italian adventure is Bologna, and you’ll save over an hour getting there by train. The Trenitalia trains are separated into three lines by speed: Frecciarosa, Frecciargento, and Frecciablanca (red arrow, silver arrow and white arrow). The red arrow (Frecciarosa) is fastest—you’ll arrive in Bologna from Milan in just an hour. This historic city is the capital of Emilia-Romagna, Italy’s most revered gastronomic region. Come hungry, because the best thing to do in Bologna is eat, eat, and eat some more. Whether you know it or not, you’re probably already familiar with some of its most famous products. Parmigiano Reggiano, Prosciutto de Parma, Mortadella, Tortellini, Balsamic Vinegar of Modena—all of these were born in the region of Emilia-Romagna.

BOLoGNA -Indulge in traditional Italian cuisine while visiting Bologna, including a variety of homemade pasta.

See Art in Florence

A quick 35-minute train ride and you’ll arrive in Florence, the artistic capital of Italy’s Tuscany region. Michelangelo’s David, Botticelli’s Birth of Venus, Ghiberti’s Gates of Paradise, and The Fountain of Neptune are just the beginning of the city’s wealth of Medieval and Renaissance art. This is the perfect opportunity to walk off some of the fun from Bologna. If you plan to visit multiple museums, save money and skip the lines by investing in the Firenze Card. For 72 Euros, you’ll have VIP access to almost all the city’s museums for a full 72 hours. After you’ve had your fill of crowds, escape with a day trip to the picturesque Tuscan towns of Siena and San Gimignano, take a winery tour in the tranquil Chianti region, or see the famed slope of the leaning tower of Pisa

Women looking at a statue in Florence.
Florence - This is the artistic capital for Italy's Tuscany region with iconic art such as Michelangelo's David, Botticelli's Birth of Venus and more!

Snap the Essential Selfie in Rome

There is more to Italy than Rome, yet that doesn’t mean you shouldn’t pay it a visit. Nearly 3,000 years of prolific history has left a mark on this city in a monumental way. From the Vatican City to the Colosseum, the Trevi Fountain, the Pantheon, and the Roman Forum, the city is full of world-famous landmarks just begging to be photographed. Plus, most of the big sites are within walking distance of each other. Wear your comfortable shoes, make frequent stops for merendas and spuntini (small meals and snacks), and lead your own walking tour of Italy’s remarkable capital. But don’t stay long, the true gems await as you continue journeying south. The short train ride is just enough time to upload your selfies to social media (yes, there’s wifi!) and take a quick nap before arriving at the next destination.

Trevi Fountain, Rome, Italy
ROME - Take a selfie together to capture you amazing time in Rome, including a snapshot in front of Trevi Fountain. 

Witness Natural Beauty in Naples

Home to catacombs and castles, palaces and piazzas, there is plenty to do in Naples. But you’ll want to save time for what lies just outside the city; this is the gateway to some of Italy’s most breathtaking natural vistas. Anchored to the East by Mount Vesuvius—the volcano that destroyed the former Roman town of Pompeii—and to the west by the sparkling Tyrrhenian Sea, the scenery surrounding Naples is a colorful contrast to the beige tones of Rome. Explore the pastel-washed fishing villages and dramatic rugged shoreline of the Amalfi Coast. Take a quick ferry ride to the isle of Capri and sip sweet limoncello with a spectacular view of the candy-colored coastline. You could even opt for a sleeper cabin on the ferry to the impossibly photogenic isle of Sicily. Soak up the views while dining on a rainbow of market-fresh produce and same-day seafood at any number of picture-perfect oceanfront restaurants.

Amalfi Coast, Italy
amalfi Coast - Don't forget to add the Amalfi Coast to your trip itinerary to explore the pastel-washed villages and dramatic rugged shoreline.

Venture Off the Beaten Piazza in Bari

The final stop on your Italian adventure might be the most intriguing of the whole trip, and you can bet few of your friends have ever seen it. The region of Puglia (the heel of Italy’s boot) is one of the least-visited and most-diverse regions in the country. Whitewashed villages cling to rocky cliffs above almost artificial-looking bright blue seas. There are the curious trulli, cone-roofed limestone structures scattered across the Provinces of Bari, Brindisi, and Taranto. The pace of life is slower, the seafood is same-day fresh, and beaches are abundant. Plus, you won’t have to stress about retracing your path back north; a sleeper cabin will eliminate the cost of accommodation for a night, save travel time, and drop you right back in Milan to catch your flight home.

Inspired by this article and want to speak with an expert travel agent about how you can plan an unforgettable vacation to Italy? Let one of Vacation’s on-call travel expertsmatch you with an Italy travel specialist, who can customize the dream trip itinerary you deserve.

Puglia, Italy
PUGLIA REGION -  Take an off-the-beaten-path excursion to explore  small villages in the Puglia region such as Alberobello.