Custom Italy Vacation Packages
Tailor made Italy vacation packages by destination, hand crafted by our Italy specialists.
Start Planning My Custom Italy VacationBrowse Italy Vacations by Who Is Traveling
We also plan around who is coming with you. These trips are built for the group as much as for the destination.
Every trip we plan starts with the style of vacation you want. Pick the one that fits below, or read the full guide to Italy vacation styles to see how the eight compare.
As one of the world’s most highly traveled vacation destinations, it comes as no surprise how many Italy Vacation Packages their are because after all, Italy offers something for every interest. Bursting with legendary art, delectable cuisine and wine, monumental architecture, an incredibly rich culture and centuries of history, the many premiere destinations within Italy cater to all types of trips. In fact, the hardest part of planning a vacation is deciding where to go and which of the country’s endless activities to add to the itinerary.
Our travel experts can help create the perfect getaway, whether for a group, families, foodies, car lovers, religious pilgrimages, or any other special interests. Travelers can choose from any of our prepared recommended itineraries or can choose to create customized experiences that cater to their specific needs and desires.
From the oceanside cliffs of Cinque Terre to the ancient ruins of Rome to the sprawling vineyards of Tuscany, travelers of all kinds are sure to experience an unforgettable adventure via a vacation package that is not only personal to them, but also guarantees to highlight the best of what Italy has to offer.
Custom Italy Vacation Packages by the Numbers
Every package on this site is built from scratch for the people taking it. These are the figures behind that, taken from what we have booked rather than from a sales page.
23 Years of Planning Italy
We have been building custom Italy vacations since 2003. The first client we ever booked is still with us, which is the number we are proudest of.
253 Custom Itineraries and Counting
Not 253 packages you pick from. 253 separate itineraries we designed for individual travelers, none of which started from a template.
14,000 Travelers Sent to Italy
Families, couples, groups and solo travelers. Between 50 and 60 percent of our group organizers come back and book us again.
20 Regions, All of Them
From Lombardy, Piedmont and Veneto in the north to Campania, Basilicata, Calabria and Sicily in the south. There is no region of Italy we do not plan.
9 Travelers Is Our Group Minimum
Below nine we plan it as a private custom trip instead, which usually works out better for a small party anyway.
2 to 12 Months of Planning Time
Twelve months ahead is comfortable and gives the widest choice. Two months is the shortest window we will take on, and we have built excellent trips inside it.
What Goes Into an Italy Vacation Package
A package here is not a shelf product. It is an itinerary we assemble around you. These are the parts we put together, and the destinations they usually run through.
The Destinations and the Highlights
Rome for the Colosseum, the Roman Forum and the Vatican. Florence for the Renaissance masterpieces and the Duomo. Venice for the canals and St Mark’s. Naples and Pompeii together, Sorrento and the Amalfi Coast at Positano and Ravello, and the islands of Capri and Ischia. Further south, Palermo, Taormina, Catania and Agrigento in Sicily, and the beaches and whitewashed towns of Puglia.
Northern Italy and Southern Italy Travel Differently
Northern Italy gives you Milan, Turin, Lake Como and the Dolomites, and it runs on fast trains and short drives. Southern Italy is slower, warmer and further apart, and the villages and countryside are the point rather than the gap between cities. We tell you which suits your dates before you commit to either.
Guides, Transfers and Timed Access
Licensed local guides for each site, private drivers and transfers between destinations, and timed entry where a queue would otherwise eat a morning. The landmarks, museums and treasures on your itinerary are booked before you travel, not negotiated at the door.
Culture, Heritage, Relaxation and Adventure
Most itineraries carry all four. A few days of culture and sightseeing in the cities, then heritage sites and countryside, then coast or lakes for the slower half, with as much walking, skiing, sailing or exploration as the group wants. The balance is yours to set and ours to build.
The Places Most Italy Packages Leave Out
Rome, Florence and Venice earn their reputation. They are also where every other package stops. These are the destinations that make an itinerary feel like yours rather than the standard route.
Tuscany Past Florence
Siena for the Piazza del Campo, San Gimignano for the towers, Pisa for more than the tower, and the Chianti countryside between them. Assisi sits just over the Umbrian border and is one of the quietest places in central Italy to spend a morning.
Bologna and the Table
Bologna is the capital of Emilia Romagna and the best eating city in the country, with Parma, Modena and the Parmigiano dairies within a short drive. This is where a taste of Italy stops being a phrase and becomes a morning with the person who made the cheese.
The South and the Islands
Lecce and the baroque towns of Apulia, Matera in Basilicata, and in Sicily Palermo, Syracuse, Modica, Ragusa, Caltagirone and the cliffs at Scala dei Turchi. The Greek temples of Agrigento and Segesta are older than anything in Rome. Apulia and Basilicata travel well together because they are neighbors.
Coastline, Riviera and the Water
The Amalfi coastline, the Ligurian Riviera at Portofino and the Cinque Terre, and the views from the Sorrento peninsula. A gondola ride in Venice is worth doing once and worth doing properly, at an hour when the canals are quiet rather than at midday.
Art Beyond the Obvious
Michelangelo in the Sistine Chapel and the David, then the Ravenna mosaics and the traditions of the workshops that still operate in Florence and Venice. Transportation between all of it is by private driver or fast train, arranged before you travel.
For centuries, Italy has been considered by poets, writers and artists to be one of the world’s most romantic countries. Home to the town that inspired the legendary love story of “Romeo and Juliet”, Verona, as well as legendary destinations for couples such as Venice, Tuscany and Rome, Italy is a dream honeymoon destination for couples from around the world.
Holding hands while walking historic cobblestone streets, indulging in incredible local cuisine, and experiencing sensational sightseeing are just a handful of romantic activities newlyweds can enjoy together. The sights offer a rich history of the world along with stunning sites, delicious culinary offerings and incredible landscapes and scenery, all of which set the perfect backdrop for a romantic getaway with your beloved.
Active couples can ski the slopes of the powder covered Alps, art lovers can stroll together in the famed Uffizi Gallery in Florence, and those looking to relax and retreat can watch the waves from the terraced cliffs of Cinque Terre. Whether celebrating a monumental anniversary in the Tuscan wine country or taking an elegant escape to the Italian Riviera for a second honeymoon.
Where Honeymoons Go
Venice, Verona and Florence for the first week, then Capri, Positano and Ravello on the Amalfi Coast, or Lake Como and Lake Garda if the second half should slow down rather than speed up.
How Long a Honeymoon Runs
Seven to ten nights for a first honeymoon across two or three bases. Ten to fourteen for a second honeymoon, which goes deeper rather than wider because the couple has usually seen Italy already.
When To Travel
May, June and September read best. Lake properties around Como, Bellagio and Stresa close through January and February, and the smaller lake towns shut almost entirely.
Trips 2 Italy knows how to create the perfect, custom getaway for any traveler, family, or special interest group. Our 20+ years of experience and vast knowledge of home country allows us to curate a custom itinerary that cater to travelers’ specific needs while showcasing the wonders of Italia.
What Gets Customized
The route, the pace, the guides, the drivers, the timed entries, the meals and which nights sit where. Nothing on this page is a fixed departure you join.
How the Planning Runs
One specialist owns your trip from the first call to the last transfer. You approve the plan before anything is booked, and you keep the same contact while you are traveling.
How Far Ahead To Start
Twelve months is comfortable and gives the widest choice of dates. Two months is the shortest window we take on, and we have built excellent trips inside it.
No two people, families, or travel groups are alike, so why should your itinerary be a carbon copy of someone else’s? We listen to our guests to ensure that what is important to them, destinations, sites, restaurants, activities, are prioritized. To enhance your experience, we’ll even suggest off the beaten path locales that only the locals would know. We believe that custom itineraries can be the difference between good and a great.
Each of our travlers have a unique view of what they think their vacation should include. For most a trip to Italy is a once in a lifetime experience and its not the time to plan a vacation to a foreign country on your own. Our staff is Italian. They know Italy and we know how to plan a vacation that will last a life. Don't just see Italy, Live IT!
What Kind Of Italy Trips Can Be Customized?
Our expert team has experience planning custom Italy vacations of a wide variety. From honeymoons to special family occasions, to special interest groups and everything in between, our custom itineraries allow for travelers to experience Italy their way.
By Trip Style
Iconic, coastal, food and wine, romantic, landscape, modern, sophisticated, off the beaten path and ski. Nine styles, each with its own regions and its own season.
By Who Is Traveling
Families, private groups, small group tours, honeymooners, reunions, cultural societies, wine clubs and shore excursion parties.
By Region
All 20 Italian regions, from Lombardy, Piedmont and Veneto in the north through Tuscany, Umbria and Lazio, down to Campania, Apulia, Basilicata, Calabria, Sicily and Sardinia.
A trip to Italy is always high on the list of trips family look to take. As these trips are on of most popular vacation, we often have special vacations deals waiting for your family. After all Italy offers something for everyone regardless of age. There are many historic locales to choose from that sure to please travelers of all ages and families of all sizes. Whether planning a yearly family vacation or a once-in-a-lifetime family reunion, a trip to Italy promises to be educational, immersive, and memorable.
Of late, we have seen many families looking to take a vacation that has a heritage component to it. These trips often mean both grand parent and grand child are taking that trip to Italy together. This can present a unique challenge to keep everyone engages and enjoying the trip. At Trips 2 Italy we have vast experience in planning custom family vacations to Italy
For families with children, we cater to younger travelers. Our experts can give great advice on activities that will keep children entertained and help spark their interest in things like art and history, all while making sure the other members of the family are satisfied as well.
Where Families Do Best
Rome for the Colosseum and the Vatican, Florence for the Accademia, Venice for the canals, then the Amalfi Coast, Sorrento or Tuscany for the part of the trip where nobody has to be anywhere.
How Long To Allow
Ten to fourteen days. Families move slower than couples, and a route that looks fine on paper turns into three hours in a car with children who have run out of patience.
What We Arrange
Private guides who actually work with children, drivers rather than rental counters, timed entries so nobody queues, and connecting rooms held early because they go first.
When it comes to exploring Italy, the experience is brought to the next level when going on vacation with a group of likeminded people who share the same interests. Group travel is a fun and exciting way to see and do new things while also spending quality time with friends, family, or fellow members of a special interest group. Having travel experts plan your group’s itinerary will make your groups trip to Italy far more enjoyable.
Our travel experts have experience in planning travel vacation of all kinds, including friend getaways and custom group travel packages. Travel clubs with specific interests such as art and architecture as well as groups of friends or family can enjoy customized escorted tour packages of locations throughout Italy and these will all be included in your Italian travel package that was created specifically for your travel group.
Food and wine groups can enjoy a culinary and wine tour of some of Italy’s most cuisine-centric regions. Groups of friends celebrating an event can enjoy a ski vacation or bond on a historic tour of Rome. No matter what type or size of group, our customized escorted tours provide travelers with itineraries that cater to their unique needs and interests.
Minimum Group Size
Nine travelers. Below that we plan it as a private custom trip instead, which usually suits a small party better anyway.
How the Money Works
Every traveler books and pays Trips 2 Italy directly, so the organizer never holds anyone’s money and the paperwork passes a finance office.
Where Groups Travel
Rome, Florence, Venice and Tuscany carry most group itineraries, with Sicily, Apulia and the Amalfi Coast for groups returning to Italy a second time.
When traveling as a group it can be difficult to find and organize an itinerary that accommodates your group’s size and varied interests. That task is even more of a struggle when trying to plan for a destination such as Italy, where there is so much to see and do. Luckily Trips 2 Italy specializes in crafting custom itineraries that can include guided tours of Italy for groups of any size.
We understand that group trips, whether for families, friends, special interest clubs, or groups from an organization, are an important time for bonding, so when planning a group vacation package, we handle the tough work of hashing out the details. We craft our itineraries with guided tours that meet your group’s needs and highlight areas throughout our country that coincide with your group’s specific interests.
Of the many types of guided tours we offer, our day sightseeing tours are one of the most popular. No matter where a group travels in Italy, there are always many incredible monuments, sites, and attractions to see. Whether exploring the historic center of Florence, taking in the best of Sicily, or visiting Rome for the first time, our knowledgeable tour guides can lead groups on a day sightseeing tour that is stress free, immersive and incredibly memorable.
Who Guides You
Licensed local guides chosen for the specific site and the specific group, not a coach courier reading from a script. Our people travel Italy year round and the relationships are theirs.
How the Days Are Shaped
Around half of each day is guided. The rest is yours, because a group that is marched from nine to six stops enjoying itself by day three.
What Is Included
Private motorcoach or drivers, timed museum entries, group meals booked where a walk-in would not get a table, and a single point of contact throughout.
Home to more UNESCO World Heritage Sites than any other country, Italy’s importance as a hub of world history and culture cannot be denied. Its countless museums and vast array of historic monuments, inspiring architecture, and classic art makes it a world capital for culture. No matter where one travels in Italy there are must-see locales and must-do cultural experiences that set Italy apart from all other travel destinations. We are travel expert that can create trips that are comprehensive cultural tours, taking travelers on an adventure through the cultural heart of the country.
For those interested in art, Italian museums are a dream come true. The Italian Renaissance art movement began in Florence, setting the tone for the rest of the world during the most influential period of artistic history. Our travel experts can add tours of historic museums like the Uffizi Gallery, Vatican Museums, and more. Both casual admirers of art and experienced collectors are sure to enjoy custom cultural tours of any number of Italy’s many museums.
For travelers looking to sightsee, there is no better location than Italy. Travelers with an appreciation for architecture can marvel at architectural accomplishments such as the Pantheon in Rome or Filippo Brunelleschi’s famed Dome in Florence. Sightseers can take photos at iconic locales such as the Leaning Tower of Pisa and St. Mark’s Basilica. No matter what type of architecture one is interested in, a custom cultural tour with one of our experienced guides can reveal interesting information and fun facts about the architecture that Italy is so famous for.
After taking in sites and museums, we love to suggest that travelers enjoy the local entertainment and festivals available all throughout Italy. We can arrange cultural tours which include insights into the local customs and highlight the activities that make each city unique. Throughout the year travelers can also immerse into the local culture by enjoying festivals alongside locals. Some of the most famous events include the several wine and food festivals during the Vendemmia (harvest period) in Tuscany, the Carnival of Venice, the Eurochocolate chocolate festival in Perugia, and Florence’s Scoppio del Carro.
The Collections
The Vatican Museums and the Sistine Chapel in Rome, the Uffizi and the Accademia in Florence, the Doge’s Palace in Venice, the Archaeological Museum in Naples and the Roman mosaics at Villa del Casale in Sicily.
Beyond the Famous Names
Ravenna’s Byzantine mosaics, Urbino in the Marche, Matera in Basilicata, and the Norman and Arab architecture of Palermo and Monreale.
How To Time It
April, May, September and October. Italy holds more UNESCO World Heritage sites than any other country, and the good ones fill to capacity between June and August.
For lovers of food and wine, there is simply no better country to explore than Italy. Just the word “Italian” conjures up images of fresh cut pasta, simply seasoned tomato sauce, and melty pizza. However, the Italian food and wine scene is vastly different than the cuisine we typically consider to be Italian.
The rich history of each region influences the area’s cuisine, often resulting in Italian food that is surprisingly multicultural. In Tuscany, one can expect simple and rustic dishes. In Piedmont, decadent and expensive ingredients such as truffles take center stage. In Umbria, recipes are made using local, seasonal ingredients.
Similarly, each region’s wine selection is varied. Whether a region produces great reds or crisp whites, the wine varieties of various regions are dependent on the history of the area, growing conditions, and the local winemaking traditions that span centuries.
For any foodie or wine connoisseur, Trips 2 Italy can help create Italian experience complete with food and wine tours. Some of the best ways to experience Italian cuisine is to take a hands-on cooking class, enjoy private dining, or tour a winery. We offer all that and more in our custom culinary tour packages.
The Food Regions
Emilia Romagna for Parmigiano Reggiano, prosciutto di Parma and aceto balsamico di Modena. Piedmont for Barolo, Barbaresco and Alba white truffles. Tuscany for Chianti Classico, Montalcino and Montepulciano. Sicily for Etna reds and Marsala.
Who Opens the Door
Producers, cellars and family kitchens are not built for tourism and the good ones are not taking walk-ins. Our specialists arrange the private visits and the tastings with the people who made the wine.
When To Come
September and October for the grape harvest, late October and November for Alba truffles. Emilia Romagna produces year round and travels well in spring.
Among the many incredible offerings of Italy that should be included in Italian vacation packages are the wide range of outdoor and sporting activities travelers can enjoy. The varied geography of the country which includes rolling hills, snowcapped mountains, vast natural forests, stunning sea views, flourishing lakeside shores, and expansive countryside sceneries makes for an outdoor vacation unlike any other.
Italy is home to some of the most amazing ski resorts in the world, making it ideal for skiing trips with family or friends. Popular locations for skiing in Italy include the Aosta Valley, Trentino Alto Adige, Veneto, Lombardy, Piedmont and even Sicily, which surprises travelers with its volcanic mountaintop that is perfect for skiing despite its Southern location.
Its nearly 5,000 miles of coastline offer an abundance of beach and water focused activities, from sunbathing to waterskiing to scuba diving. Oceanside locales such as the Amalfi Coast and Cinque Terre as well as lakeside retreats in the Italian Lake district (comprised of Lakes Como, Garda, and Maggiore) allow travelers to enjoy waterfront views and activities without missing out on the culture of Italy.
Whether interested in hiking the cliffside trails of Cinque Terre, biking the roads of the Italian countryside, or skiing the mountains of Trentino-Alto Adige, Trips 2 Italy can help sporting enthusiasts create custom Italian vacation packages that exceed their expectations.
Where To Go On Foot
The Dolomites around Cortina d’Ampezzo, Val Gardena and Alpe di Siusi, the Cinque Terre coastal paths in Liguria, and the Gran Sasso and Majella parks in Abruzzo.
On Snow
Dolomiti Superski links twelve areas through the Sella Ronda. The Aosta Valley has Courmayeur and Cervinia, and Lombardy has Bormio, Livigno and Madesimo. Italian slope colors run blue for easiest, red for intermediate, black for expert.
On the Water
Sailing the Costa Smeralda in Sardinia, the Amalfi Coast by private boat with its crew, and the northern lakes. Time on the water is planned as part of the whole itinerary.
Ready To Start Planning Your Trip To Italy?
Browse Italy Vacation Packages by Region
Choose a region to explore its custom vacation packages, then we tailor the itinerary to you.