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Italy Vacation Packages & Private Tours

Thanks to our dedicated team in Italy we can take you beyond the basics to discover the country's hidden gems. Whether it's your first Italian vacation or your tenth, we can create the perfect Italy itinerary for you.

You can travel Italy in classic "semi-independent" JayWay style with the benefit of our local staff's assistance before and during your trip, join one of our small group tours or take a private escorted tour with Daniele, our Italy country manager. Whichever style you choose, your Italy vacation package is guaranteed to surprise and delight in equal measure.

Italy


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Popular Italy Vacation Itineraries

Italy's a country that requires repeat visits. Our Italy vacation ideas have something for you whether it's your first time or your fifth. Our suggested itineraries for Italy and neighboring countries allow you to enjoy a multi-destination tour with ease. Our vacation packages make traveling in Italy and neighboring countries truly hassle-free. We take care of getting you from place to place, accommodation, excursions, and activities. For each of these itineraries, you can get a rough idea of the price using the Price Guide function.

Glowing Reviews from Our Guests

5.0 / 5

Average of our Guest's Ratings of our Italian vacation packages, based on 74 reviews

Review by Shanna & Michael
Shanna & Michael
Illinois

If you're thinking about whether or not to use the service, don't think twice! Our vacation was a 10 out of 10 because of JayWay Travel.

If you're thinking about whether or not to use the service, don't think twice! Our vacation was a 10 out of 10 because of JayWay Travel.

Year : 2022
Visited : Italy
Itinerary : Florence, Sorrento
Rating :
5 / 5
Year : 2022
Visited : Italy
Itinerary : Florence, Sorrento
Rating :
5 / 5
Review by Eileen, Boyer, Rowan, Nolan & Aine
Eileen, Boyer, Rowan, Nolan & Aine
New York

Overall smooth seamless transition of all the planning into reality!! Thank You!

Overall smooth seamless transition of all the planning into reality!! Thank You!

Year : 2022
Visited : Italy
Itinerary : Venice, Florence, Rome, Sorrento
Rating :
5 / 5
Year : 2022
Visited : Italy
Itinerary : Venice, Florence, Rome, Sorrento
Rating :
5 / 5
Review by Mark & Karen
Mark & Karen
New York

JayWay Travel's degree of professionalism and detail was unsurpassed. Exceeded our expectations!

JayWay Travel's degree of professionalism and detail was unsurpassed. Exceeded our expectations!

Year : 2022
Visited : Italy
Itinerary : Palermo, Ragusa, Siracusa, Etna, Salina, Lipari, Catania
Rating :
5 / 5
Year : 2022
Visited : Italy
Itinerary : Palermo, Ragusa, Siracusa, Etna, Salina, Lipari, Catania
Rating :
5 / 5

Start With Italy's Most Famous Destinations

It's almost impossible to visit Italy without at least passing through Rome. All roads truly do lead there. Whether it's your first or fifteenth time in the Eternal City, you're always going to find something new, like a recently uncovered part of Ancient Rome. First-timers shouldn't miss the Colosseum, Roman Forum and Vatican City but who could deny the pleasure of a gelato while gazing at the Trevi Fountain? 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 Accademia and the Uffizi Gallery you'll find a wealth of Renaissance art and architectural delights. As a major tourist destination in its own right, Venice is hard to beat. It can be busy to the point of bursting at peak times but Venice is a joy out of season. It should definitely be on everyone's list of must-sees in Italy. A big advantage of staying overnight is that you get to enjoy it after the cruise ship crowds have left. A sunset gondola ride with a glass of prosecco, followed by a stroll across St Mark's Square is the ideal start or end to a tour of Italy.

Let Us Take You Beyond Italy's Holy Trinity

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, or to Pisa's leaning tower, provide plenty of sightseeing opportunities when you tire of the Tuscan countryside's rolling hills, wineries, and medieval hill 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.

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. This favorite of the Hollywood set is a glamorous option for some extended time by the water. Head to Sicily and you can experience a microcosm of Italy. 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.

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. Capri , in the Gulf of Naples is an idyllic island beloved by honeymooners, drawn there by the famous Blue Grotto.

Vacation like an Italian

If you want to take a vacation as the locals do, then Puglia should be on your list. Still under the mass tourism radar, it's a welcome change of pace. Puglia's small coastal towns give way to vast olive groves and then hills dotted with the signature conical trulli houses. The island of Sicily is Italy in miniature. It's packed with UNESCO Sites, historic towns, national parks, and fantastic local dishes. Did you know Sicily has several island groups off its coast? The volcanic Aeolian Islands are the perfect place for someone who feels like they've already seen and done everything in Italy. If you've ever wondered why Italians don't go abroad for beaches, it's because Sardinia's abundant white sand beaches with iridescent blue water look like the Maldives.

Want to 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 Italian 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 and stress-free 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.

More Videos About Italy

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, and there are many destinations that are wonderful to experience outside the normal tourist season. The 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. In winter months the south, especially Sicily, has very mild weather. If you're more interested in history, food, and culture than beaches, winter can be the ideal time to visit. Our travel advisors are keen to help you explore the best of Italy at any time of year.
How long do I need to see Italy?
Italy's a country packed with beautiful sights, from ancient cities to spectacular landscapes. It could take years to properly explore all of Italy. Most of us aren't lucky enough to have unlimited money and time, so we have to focus. You could confine yourself to the classic trifecta of Rome, Florence and Venice, ideally with at least three days in each, or focus in on a region if you have a shorter time or already know you'll be back for more! We offer many of Italy's most interesting destinations, going far beyond the obvious. Our travel advisors have had the benefit of considerable years of visiting and living in Italy and can help you pick where to spend your time for the maximum enjoyment.
Where should I go in Italy?
Italy is rich in wonders and as one of our friends likes to say "extends from the Alps, to Africa". Whether you want mountains, lakes, gentle hills, Maldives-style beaches, ancient cities or historic towns, our travel advisors will help you pick the ideal spots for your vacation whether you want to stick to the well-known highlights or visit less famous delights.
What's included in your Italy vacation packages?
We start by working with you to plan your vacation, your route, and where you're spending each night. A private Italy tour offers you complete freedom to create your dream itinerary. You'll get to pick from a shortlist of recommended accommodations. You can also decide how you'd like to get around Italy. Arrival and departure airport transfers are always included in our Italy trips. We can arrange train tickets or a private driver. You can pick which guided tours including city sights, galleries and museums, and other activities like wine tasting, cooking classes, and many more that you'd like to include at this point or wait until it's closer to your arrival, when you'll be in touch with our local staff in Italy. Once you land those staff are available to you by phone or email to assist with whatever you need.
It's my first trip to Italy, should I go to Rome, Florence and Venice?
It's tempting to want to tick off the "Holy Trinity" of Italian tourist destinations, and many people do. The Colosseum, the Sistine Chapel, the Vatican Museums, Michelangelo's David and St Mark's Square are all powerful attractions. Yet there is so much to see in and around each of these places that you could easily pick just to one or two of these major cities and see lesser-known places along the way in between. Our extensive coverage and knowledge of Italy means we can create whatever kind of trip you're looking for.
Do you offer escorted tours of Italy?
Our small group tours of Italy are all escorted tours. Our Italy country manager Daniele will be your tour director and guide over several days, with local guides at certain sites. If you prefer a private escorted tour we are more than happy to plan a trip that covers all the destinations you wish.
How much does a private tour of Italy cost?
Our custom Italy vacation packages of accommodation, transfers and activities start at around $250 per person per day, but you can get a rough estimate based on any of the itineraries on our site by using the Price Guide function. Choose which class of hotel you prefer, the size of your party and the month you wish to travel in and an estimated total price will be generated for you. Included in the price is our expert planning service and support throughout your custom tour of Italy.
What is Italian cuisine like?

Italy is home to perhaps the world's most famous cuisine, with delicacies and dishes 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 food, 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. Italy's food and wine traditions are an important part of the culture so we prepared a guide to some dos and don'ts when dining in Italy.

What should I drink in Italy?
Italy 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. Italy also has a burgeoning craft beer scene to supplement the ubiquitous Peroni and Moretti brands. Local water is usually safe (some cities, such as Rome, have decorative fountains that double as drinking fountains), but we generally recommend bottled water.
What is public 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 often the best way to get between destinations quickly. Long distance buses aren't the most comfortable and are only popular for reasons of cost. They don't often cover routes not already served by trains. If you'd prefer a door-to-door service over taking the train we can arrange private transfers and include stops along the way.
Can I self-drive on my Italian vacation?
Although Italy's cities are well connected with high-speed train services, regions such as Puglia or Tuscany aren't so well served by public transport. An Italy road trip can be a great way to see more of the country and a rental car is a cost-effective way to get around. Driving in Italy isn't as terrifying as you may have been led to believe, outside the major cities at least. We can include car rental in the custom Italy vacation package we prepare for you.

If you'd prefer not to drive, we can arrange a guide and driver, or just a driver, to transport you between overnight destinations, stopping at points of interest en route.
How many UNESCO World Heritage Sites does Italy have?
The Italian Peninsula's rich history, from the Etruscans, ancient Greek colonies, the vast Roman Empire, the Renaissance, and its dramatic natural beauty means you're never far from a UNESCO World Heritage Site in Italy. There is a total of 58 on the main list and another 31 on the Tentative List. Fun fact: the UNESCO logo is based on the ancient Greek Temple of Concordia in Agrigento, Sicily
Is traveling in 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.
Can I mix private and group excursions and activities in my Italy vacation package?
In many locations, we offer both options; either with a private tour guide just for you and your party or small group tours. Although your overall Italy tour will be a private one, based on your dates and preferences, you can enjoy the social aspects of a group tour by opting to take some group excursions. We emphasize small group sizes wherever possible on the group excursions we offer. A bike tour is often more enjoyable in a small group.
Which other countries could I visit in addition to Italy?
We often create itineraries combining Italy with Croatia and Slovenia as well as other countries around the Adriatic Sea. Another common pairing is Switzerland and Northern Italy. If visiting Sicily, Malta is just a short flight away. Antiquities enthusiasts often ask us to create itineraries that feature Italy and Greece.
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