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. After much research are pleased to offer two ways to see Italy. You could go as part of a small group tour focusing on regional food, history and culture with our expert guide and Italy Country Manager Daniele. Or go in classic JayWay style, traveling independently with a complete vacation package including the benefit of our 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. There's even a saying to that effect. 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. 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.

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. 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. Starting in 2018 you can explore Sicily with us on a week-long escorted gourmet & culture tour.

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 sun-bathing 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 with the expectations of it being neat and tidy. It's a melting pot of a place and has been for over two thousand years. Dig beneath the surface though and you can't help but be enchanted by this chaotic metropolis. 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.

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 on your own. You'll taste some of the country's signature products. And you can meet the skilled artisans who make them. Besides the 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 groups upon request.

Italy vacation experts

Accommodation in Italy runs the gamut from farm stays to luxurious palazzos. Our local guides will be on-hand to assist all vacationers. Wherever you want to travel in Italy, we can make it happen. 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 Italy vacation, just for you.

Venice Florence Amalfi Coast Gourmet Tours Rome Milan Tuscany Cinque Terre Lake Como Naples Bologna Puglia Piemonte

  Average guest ratings of our Italy vacation packages:

(4.8/5 based on 5 reviews)

"If you're visiting Croatia, and you should, JayWay will put together a great trip for you and then will be there for you every step of the way.  Carmine was great, put together the perfect itinerary for us. We felt we were in good hands with Lidija. Very responsive."

Jonathan & Greg

New York

"The trip went so smoothly it was the most perfect honeymoon. Everyone we met and/or assisted in planning our trip was very helpful. JayWay gave us excellent customer service, fantastic accommodation, and a great vacation at a great price."

Anita & Matt

Chicago, IL