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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. 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 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. 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. 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.

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 in the world

Italy is home to more UNESCO World Heritage Sites than any other country on earth and many that are on the tentative 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 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 escorted tour groups upon request.

Italy 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 accommodation we offer in Italy runs the gamut from farm stays to luxurious palazzos. Our local staff and guides will be on-hand to assist and inform 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 trip to Italy, just for you.

Top vacation destinations in Italy

Amalfi Coast
Gourmet Tours
Cinque Terre
Lake Como

  Average guest ratings of our Italy vacation packages:
(4.9/5 based on 12 reviews)

"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

Anita & Matt

Chicago, IL

From the beginning we always felt like a priority with quick and informative responses. We had the most memorable honeymoon thanks to the JayWay Travel team.

Megan and Roby

Megan and Roby


Popular Italy Vacation Itineraries

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

Italy Tours

Condensed Italian Classics: Rome, Florence & Venice in a Week

A high-speed tour of Italy's big name destinations. Ideally you'd have a few more days to appreciate them fully, but if time is of the essence… read full itinerary

One Week Rome & Tuscany Tour

Enjoy some of Italy's most wondrous jewels, Rome, Tuscany and Florence. You'll get a real taste of the Italy's most loved rural region in between revelling in Rome's magnificence and feasting on fine art in Florence. read full itinerary

One Week Italy Dream Honeymoon: Rome & Amalfi Coast

Where better to go on your first trip as a married couple than Romantic Rome and the amazing Amalfi Coast. We'll make your trip seamless, leaving you to enjoy your special time together. read full itinerary

Highlights of Eastern Sicily in a Week

Some of Sicily's brightest gems are found on the eastern side of the island. In a week you'll see Taormina, Mt, Etna, Ragusa and Siracusa. read full itinerary

9 Days in Northern Italy: Milan, Lake Como & Venice

Spend 9 days exploring the very different sides of Northern Italy. Start in business-first Milan, the country's fashion and financial capital. From there you'll head to Lake Como to enjoy some time on the water and surrounded by the beauty of the lake region. The last stop is La Serenissima, Venice. The Queen of the Adriatic and a city like no other, it has to be seen to be believed. read full itinerary

Italian Classic Beauty: Rome, Florence, Venice in 10 days by train

Three classic Italian beauties. Start in the eternal city, Italy's magnificent capital Rome. Next comes Renaisasance masterpiece Florence, then the Queen of the Adriatic, Venice. With transport by high speed train between the cities. read full itinerary

Italian Dream Honeymoon

This ten day Italian honeymoon itinerary packs in Rome, Tuscany, Florence and Venice. Explore the Eternal City hand in hand. Relax poolside at a Tuscan farmhouse or palazzo. See the best of Florence in a day then spend the last three days in one of the most romantic cities in the world, Venice. read full itinerary

Italian Highlights in 11 Days: Rome, Tuscany, Cinque Terre & Venice

See Rome, Tuscany, Cinque Terre & Venice in a week and a half if traveling at a fast pace or take it slow and use this as a base for a longer tour and add some days. read full itinerary

Best of Sicily (Palermo to Catania) in 11 days

Find out for yourself why everyone's talking about Sicily. Italy in miniature is how we think of it and we know you'll love this magnificent island. Explore from regal Palermo to Catania by way of the valley of the temples at Agrigento, Baroque gem Ragusa Ibla, ancient Greek town Siracusa, bustling Catania, majestic Mt Etna and darling of the early jetset, Taormina. read full itinerary

Magical Italy: Rome, Amalfi, Tuscany, Florence, Venice in 2 weeks

Two weeks exploring some of Italy's highest highlights, starting in Rome, then the Amalfi Coast, followed by Tuscany, then Florence, finishing up in Venice. Truly magical! read full itinerary

Two Weeks Grand Tour of Italy

A veritable Grand Tour of Italy hitting many of the country's most popular destinations. After landing in Naples, you'll go straight to the Amalfi Coast, After that it's Rome, followed by the artisitic treasures of Florence. Back to the coast, with Cinque Terre followed by stays in Milan and finally Venice. read full itinerary

Tours of Italy and neighboring countries

12 Days Honeymoon in Venice & Southern Croatia

The perfect honeymoon combination: Venice, one of the most romantic cities in the world coupled with the highlights of Croatia's Dalmatian coast. Marvel at the majesty of Venice. Be awestruck by the beauty of Dubrovnik. Relax on Hvar, Europe's sunniest island. Wander in the cosy backstreets of the old city of Split. read full itinerary

The Best of Italy & Austria in 12 Days

Combine Italy and its northern neighbor Austria on this 12 day tour. With time in Rome, Venice, Salzburg and Vienna you'll see some of Europe's most wonderful cities, with thousands of years of history and three empires between them. read full itinerary

Rome and the Jewels of the Adriatic

A 2 week Greatest Hits tour. Start out by seeing the splendor of Rome, also ideal for flight connections to the US. From there it's a short flight across the Adriatic Sea to Dubrovnik, the first of three Croatian classic destinations. Some island time on Hvar follows, then Split, essentially a Roman emperor's retirement palace. The final stop is Venice, reached by another short flight. read full itinerary

The Best of Italy & Slovenia in 2 Weeks

This two week trip will have you experiencing the highlights of two beautiful countries. From bustling Rome, all the way to Ljubljana, the super-cute capital of Slovenia, with overnight stops in Florence, Venice and the Julian Alps along the way. read full itinerary

Adriatic Adventure - Croatia and Venice in 2 Weeks

Experience the very best of the Adriatic coast, from its Pearl, to its Queen. Starting in Dubrovnik over 2 weeks, you'll have some island time on Hvar and go Roman in Split – and that's just the first week! Next see the spectacular Plitvice Lakes before spending a few days in old-Venetian coastal town of Rovinj. Then finish up in La Serenissima itself, Venice! read full itinerary

Latest articles about Italy from the JayWay Travel Blog   -   read more

The Best Spa Towns in Central and Eastern Europe

Some very relaxing news for visitors to Central and Eastern Europe: a new international project has united the best spa towns in Central and Eastern Europe in an effort to earn UNESCO more...

Things to Do in Puglia: History, Relaxation, and Really Good Food

Oh, Italy. It's hard to decide which city and region to love best. Regal Rome? Vivacious Venice? Luscious Naples? There's something wonderful about each of them. But Puglia is in a class more...

Your Reading List for Venice

This week we continue our books for travel blog series with the legendary city of Venice! One of the highlights of Italy, Venice is a place with unmistakeable romantic charm. It's a truly more...

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