Top vacation destinations in Italy

We're big fans of Italy here at JayWay. We've held three of our team meetings there in the past five years. Our team and destination map in this magnificent and varied country are continually expanding. We are pleased to offer two ways to see and explore Italy. You could join a small group tour focusing on regional food, history, and culture with our expert guide and Italy Country Manager Daniele, or even put together a group of friends to take a private escorted tour based on those itineraries. Or go in classic JayWay style, traveling semi-independently with a complete vacation package including the benefit of our local staff's assistance before and during your trip. Either way, you'll have an unforgettable Italian vacation.

Take your pick of Italy's most famous destinations

It's almost impossible to visit Italy without at least passing through Rome. All roads truly do lead there. But whether it's your first or fifteenth time in the Eternal City, you're always going to find something new. Florence is often referred to as Italy's art gallery. Millions come every year to admire Michelangelo's David. Both outside and inside the city's famous galleries you'll find a wealth of artistic and architectural delights.

If Florence interests you, but you would prefer to explore vineyards and forests out in the countryside, the region of Tuscany provides a soothing balm. Day trips to Florence and Siena provide plenty of sightseeing opportunities when you tire of the Tuscan countryside's rolling hills, wineries, and hilltop towns and villages like UNESCO-listed San Gimignano. Nearby Bologna is home to the world's oldest university, and with its wealth and preserved Old Town, often tops rankings of the best places to live in Italy. The surrounding Emilia Romagna region is also famous for its fast cars and slow food.

As a major tourist destination in its own right Venice is hard to beat. It's busy to the point of bursting at peak times but a joy out of season. It should definitely be on everyone's list of must-sees in Italy. A big advantage of staying overnight in Venice is that you get to enjoy it after the cruise ship crowds have left. Visitors to Venice are never disappointed.

Proud of its status as the financial capital of Italy, Milan is an ideal place to start or finish a tour of Italy. There are a huge number of direct flights to the US and plenty to see and do for a couple of days. The grand Duomo and Da Vinci's Last Supper are but two highlights. Milan also has some of the best fashion shopping in the world set in the grand arcades. This provides a modern day distraction to the impressive cathedral that dominates the center of the city. The Navigli area of the city is packed with places to enjoy the favorite Milanese pastime of aperitivo. Lake Como is quite close by, and this favorite of the Hollywood set is a glamorous option for some extended time by the water. Head to Sicily and you can experience Italy in microcosm. In every major destination anywhere in the country we can arrange a walking tour with an expert local guide so you'll learn the stories that make each corner of this magnificent country unique.

More UNESCO World Heritage Sites than anywhere else

Italy is home to more UNESCO World Heritage Sites than any other country on Earth, and many more are on the candidates list. From ancient ruins to historical monuments and natural landscapes, this is a country whose greatest hits album goes on and on. Italy really is the ideal place for the perfect vacation.

Italy's coastal gems

Italy's coastline is studded with gems. It's a tough choice between Cinque Terre in the north or its southern counterpart, the Amalfi Coast. With our handpicked selection of hotels and guest houses and expert advice on how best to experience these places, you can be sure of a fantastic time by the sea. While not renowned for their beaches, we know a few places where you can get some quality sunbathing in! The ancient port city of Naples might best be considered a diamond in the rough. It's a love-or-hate kind of city and somewhere you don't go there expecting a neat and tidy city. It has been a melting pot for over two thousand years. Dig beneath the surface though and you can't help but be enchanted by this chaotic metropolis. Neighboring Capri is an idyllic island beloved by honeymooners. If you want to take a vacation like the locals do, then Puglia should be on your list. Still under the mass tourism radar, it's a welcome change of pace. The island of Sicily is Italy in miniature. It's packed with UNESCO Sites, historic towns, national parks, and fantastic local dishes.

Taste the very best of Italy

We believe that the very best of Italy isn't to be found only in the cities, but also in the countryside. These are the places where centuries of tradition and an obsession with only the very best wines and foods combine to produce exceptional products. Our small group tours get to the heart of Italy, its food. Daniele's connections open doors that you wouldn't be able to pass through on your own. You'll taste some of the country's signature products, you'll prepare delicious meals in private cooking classes. And you can meet the skilled artisans who make them. These are more than simple food and wine tours. Besides outstanding gourmet experiences you will visit sites of cultural and historic significance. We have a rich schedule of tours in several different regions. These make the perfect accompaniment to some independent exploration of the land of la dolce vita. We can even put together custom tours for your own private escorted tour groups upon request. Exploring the culture and cuisine on an Italy tour with a private guide is a treat for all the senses.

We're Italian vacation experts

We're more than an Italy travel agent. We are Italian vacation experts. Our seamless customized Italy vacation packages start with inside-out knowledge of our destinations. The carefully chosen lodgings we offer in Italy range from farm stays to luxurious palazzos. Our English-speaking local staff, drivers and guides are on-hand to assist. Whether it's about what to do and see, whether it's on a private tour, an organized excursion or just suggestions on how to spend some free time. Wherever you want to travel in Italy, we can make it happen. A travel agency or the mass market tour operators might make a few bookings for you. But we'll be with you every step of the way to ensure a spectacular trip that you'll remember forever. With a country so densely packed with riches, there will always be somewhere new to visit. Even if your desired destination isn't listed here, rest assured we can still include it in your custom trip plan. Contact us for a free travel consultation. We'll start planning the perfect trip to Italy, just for you.