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Italy Vacation & Tour Packages

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 and 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 fiftieth 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 Michaelangelo'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 and day trips to Florence and Siena provide plenty of sightseeing opportunities when you tire of rolling hills, wineries, and hilltop villages. 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, including Italy's best cheeses.

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 overnighting 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.

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 its 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

Should a coastal stay be of interest, you can take your pick of 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 to expecting a neat and tidy city. It has been a melting pot of a place 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 just like the locals do, then Puglia should be on your list. Still under the mass tourism radar, it's a welcome change of pace. With its many UNESCO Sites, national parks, and fantastic local dishes, the large island of Sicily is Italy in miniature.

Taste the very best of Italy

We believe that the very best of Italy isn't to be found just 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. 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.

Italian vacation experts

We're more than an Italy travel agent. We are Italian vacation experts. Our seamless Italy vacation packages start with inside-out knowledge of our destinations. The handpicked accommodations we offer in Italy range from farm stays to luxurious palazzos. Our local staff and guides will be on-hand to assist and inform all vacationers about what to do and see, whether it's on 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 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 then we'll start planning the perfect trip to Italy, just for you.

Explore Our Destinations in and Around Italy

Popular Italy Vacation Itineraries

Our suggested itineraries in Italy and neighboring countries allow you to enjoy a multi-destination tour with ease. Our vacation packages make traveling in Central & Eastern Europe hassle-free. We take care of getting you from place to place, accommodation, excursions and activities.

Glowing Reviews from Our Guests

4.9 / 5

Average of our Guest's Ratings of our Italian vacation packages
Based on 32 reviews

Mike & Kirsten

Nebraska

JayWay Travel is a company that will take most of the hassles of planning an international trip. From budgeting, preplanning ideas and execution. JayWay Travel help build the trip that you want instead of following someone else's itinerary.

JayWay Travel is a company that will take most of the hassles of planning an international trip. From budgeting, preplanning ideas and execution. JayWay Travel help build the trip that you want instead of following someone else's itinerary.

Year : 2019
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Venice
Rating :
5 / 5
Year : 2019
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Venice
Rating :
5 / 5

Alexander & Irina

New York

JayWay Travel delivers the best personalized high quality hassle free travel experience.

JayWay Travel delivers the best personalized high quality hassle free travel experience.

Year : 2019
Visited : Italy
Itinerary : Florence, Rome, Positano
Rating :
5 / 5
Year : 2019
Visited : Italy
Itinerary : Florence, Rome, Positano
Rating :
5 / 5

Megan & Jason

Missouri

JayWay Travel turned our dream honeymoon into reality. From help with the accommodations, transfers between cities, daily excursions and so much more, we had the best time. We can’t wait to go on another JayWay vacation.

JayWay Travel turned our dream honeymoon into reality. From help with the accommodations, transfers between cities, daily excursions and so much more, we had the best time. We can’t wait to go on another JayWay vacation.

Year : 2019
Visited : Italy, Croatia
Itinerary : Castellina in Chianti, Rome, Dubrovnik, Hvar, Split
Rating :
4.8 / 5
Year : 2019
Visited : Italy, Croatia
Itinerary : Castellina in Chianti, Rome, Dubrovnik, Hvar, Split
Rating :
4.8 / 5

Frequently Asked Questions about travel to Italy

When is the best time to visit Italy?

As a long peninsula stretching deep into the Mediterranean from the Alps, Italy’s weather can vary greatly. We tend to recommend visiting either from late April to early June, or from mid-September to mid-October. Italy's key sites can be crowded in the peak summer months of July and August, and the heat in the cities can be overwhelming, but this is the perfect time to travel to lesser-known regions and destinations and our travel advisors are keen to help you explore the best of Italy at any time of year.

Is Italy safe?

Italy is generally safe, but you’ll want to keep an eye out for bag-snatchers and pickpockets, especially on public transport or in touristy areas. If driving, be sure not to leave valuables in your car. Although southern Italy is infamous for organized crime, these gangsters are rarely involved in petty crime affecting tourists, preferring to focus on other activities, such as drug trafficking and racketeering. Although you should keep your wits about you in Naples’ old town, its petty crime rates are on par with Barcelona, Marseilles, and Amsterdam.

What is Italian cuisine like?

Italy is home to perhaps the world's most famous cuisine, with foods popular with people from millionaires to children and grad students. The dishes that you might be familiar with from Italian restaurants abroad (especially chains like Olive Garden!) are a poor introduction to Italian cuisine, however, as it varies greatly from region to region. Until Italy unified 150 years ago, it was a bewildering hodgepodge of kingdoms, democracies, and a theocracy, speaking different languages. This is reflected in the local foods. Trieste has excellent pastries, but a decent pizza is rare up there, while you'll be hard-pressed to find a perfect risotto in Sicily. In each region or destination you visit, we'll provide dining suggestions to help you explore local traditions via food and drink.

What is transportation like in Italy?

Italian cities can be chaotic, especially Naples and Rome, with aggressive drivers, constant traffic jams, and overcrowded subways and buses. Italian cities and towns are best explored by foot, and we prioritize centrally-located accommodations, to help you do so. The high-speed express trains that serve major cities are modern, frequent, and are an excellent way to get between destinations quickly. We often arrange private transfers, which let you make stops between destinations, such as to visit Tuscan hill towns. Italian highways are modern, although most charge tolls. We tend to advise against car rental for city-based itineraries, as Italian drivers are aggressive, urban traffic heavy, parking very difficult to find, and areas where most cars are banned can be poorly marked. Conversely some regions, such as Puglia, lend themselves well to self-drive exploration.

What should I drink in Italy?

Italy similarly has a vast array of wine varieties (at every possible price point). As vineyards can be found in every part of the country, we recommend seeking out local wines, which often perfectly match the local food, and are always available. Italy produces some good beers, especially its increasingly popular micro-brews. People seeking something stronger should seek out Grappa (brandy made from leftovers from wine production), or Limoncello (a sweet lemon liqueur popular in the south). A common digestif is Amaro, a bittersweet liqueur. Local water is usually safe (some cities, such as Rome, have decorative fountains that double as drinking fountains), but we generally recommend bottled water.
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