Italy is an iconic destination with a rich cultural heritage. From the Dolomites and alpine lakes of the north to the idyllic countryside of Tuscany, and from the rugged coastlines of Cinque Terre, Amalfi, and Sicily to classic cities like Rome, Florence, and Venice, Italy offers ancient ruins, world class art, iconic architecture, and delicious food and wine.
Explore iconic Italy with one of our best-selling vacation packages. Choose from our most popular Italian city combinations, customize your flights, hotels and number of nights, then add transfers and activities to create your dream vacation to Rome, Florence, Venice, and more!
Our #1 Bestseller to Italy!. Visit these fascinating cities: Rome (with stunning Colosseum, Roman Forum and delicious food) after that, travel north ...
Visit: Florence, Rome, Venice
Take Italy into your own hands!. Start in Venice (sumptuous palaces and romantic waterways), after that, trains rides will take you to Florence (home ...
Visit: Florence, Naples, Rome, Sorrento, Venice
Experience Italy by train!. Travel to Rome (famous for the Colosseum, Roman Forum, Vatican and delicious food), after that, Cinque Terre (five miles ...
Visit: Cinque Terre Area, Florence, Rome, Venice
Combine glorious cities in Italy with this fun vacation!. Visit Rome (the Eternal City, with its stunning Colosseum, Roman Forum and delicious food) ...
Visit: Florence, Rome, Siena, Venice
One of our most popular vacation packages, offering an incredible introduction to Italy!. Discover Rome (the Eternal City, with the Colosseum, Roman ...
Visit: Florence, Milan, Rome, Venice
Enjoy style and ease while discovering rich cultural heritage, classic food, and impossible beauty.
Visit: Amalfi Coast, Amalfi Town, Florence, Naples, Rome, Venice
Everything was great! I have no complaints.
Traveled on: 09/08/2025
Discover history, religion, art, and ancient ruins in Italy's charming towns and vibrant cities. Whether it's wine tastings in Tuscany, sunbathing in Amalfi, cruising the canals of Venice, or shopping of Milan, Italy offers something for everyone!
Not sure what to see or do, or where to start when planning your trip? Try one of our vacation package ideas that includes tours based on your interests, or maybe a package including private car transfers between your destinations! From culinary experiences to cultural attractions, you deserve a vacation tailored just for you!
Explore favorite Italian cities and hidden gems, including Montepulciano and UNESCO-listed cities Ferrara and San Gimignano, with private transfers.
Artistic Italy calls to you!. What can be said about these magnificent cities: Rome (the Eternal City is a living museum and houses untold treasures ...
Discover rich heritage sites of the Italian capital and other main cities!. Explore historic highlights and consequential neighborhoods of the Eternal ...
Stunning architecture, ancient ruins, world-class museums, charming UNESCO listed towns, and delicious food and wine! The best of Italy is yours to ...
Explore Tuscany and The Italian Riviera with a private driver, including stops to discover Lucca,Prato and Castello di Lerici.
From the Roman Empire to the Renaissance, Italy is famous for its huge contributions to the worlds of art, architecture, fashion, opera, literature, design, and film – the list goes on, and we haven`t even mentioned the food yet. The country has more UNESCO World Heritage cultural sites than any other country in the world.
Artistic masterpieces, medieval hill towns, majestic mountains, Mediterranean beaches, bustling markets and mouth-watering cuisine - Italy really is a country that has it all, and that's why it is one of the most-traveled destinations in Europe.
There are so many highlights in this gorgeous country - from the canals of Venice to the museums of Florence and the surrounding countryside of Tuscany and its Hill Towns
to the cobblestone streets of Rome to the cliffs of Positano… and beyond.
Rome is one of the most iconic and most traveled cities in Europe and you could spend days getting lost in this amazing destination. The most picturesque spots in Italy might just be Cinque Terre and all the stops along the Amalfi Coast. Positano is the gem of the Amalfi Coast and is arguably the most beautiful and most charming town in the whole of Italy.
Like all popular European destinations, Italy sees visitors throughout the year - rain, snow or shine. And all of these are a possibility depending on when you visit Italy. Every season in this country has its charm, as well as its drawbacks, so when to go depends on your travel type and what activities you are interested in.
Generally speaking, the best times to visit are during the `shoulder seasons` which is spring (April to June) or fall (September and October) when there are fewer tourists, lower prices, and moderate temperatures. The summer months bring an influx of tourists and increases in hotel rates, and higher temperatures. The winter months are often grey, wet, and cold in the north but temperate south of Rome. Here is an overview of Italy in all four seasons that will help you decide what`s the best time of year for you to visit. For more information, check out: Best Time to Visit Italy
We recommend 7-10 days based on what you want to see and do. We offer flexible vacation packages so you can select your number of nights in each city, desired hotel and activities. We suggest a minimum of 3 nights in larger cities.
Whatever your pleasure, transportation in Italy is modern, easy to navigate and fits a variety of budget ranges.
By Car:
If it's the open road you're after, renting a car is the best way to travel in Italy. All the typical car rental companies are available at the major airports. Specify automatic or manual transmission, as car transportation in Italy (and Europe, for that matter) is usually manual. On the small, winding country roads, manners usually win out, and major highways span the country to help ease access to the major cities. For more information on getting around by car, check out: Driving in Italy
By Train:
Train travel in Italy is an excellent way to take the stress out of planning routes. Though you can't get to the smallest towns by train, the medium-sized and, of course, the major stops are on train routes.
The currency of Italy is the Euro. US dollars are not accepted. Please be sure to have the correct currency on hand or be prepared to exchange your dollars for euros upon arrival. Currency exchange desks can be found at the airport and many locations throughout the city. For more detailed information, consult our guide by clicking here Tipping in Italy.
English may be spoken at your hotel and in the tourist areas, but not everywhere. We suggest you get a good English-Italian guidebook and familiarize yourself with common phrases such as hello, goodbye, excuse me and numbers 1-10.
Rome - Florence - Venice with Signature Transfers (7 nights)
Explore our favorite Italian cities and hidden gems, including Montepulciano and UNESCO-listed cities Ferrara and San Gimignano, with private transfers. Begin this twist on our classic Italy getaway in historic Rome (the Eternal City) where the Colosseum looms large and the Vatican's treasures await discovery, and after that, travel to Florence (the capital of Tuscany and cradle of the Renaissance), until you finally reach Venice (the intimate city set on canals famous for gondola rides). Enjoy private transfers between each city that allow you to avoid the hassle of train stations and explore the following scenic towns: Montepulciano (renowned for its exquisite Vino Nobile Wine), San Gimignano (characterized by its medieval architectural towers) and Ferrara (a well-preserved UNESCO-listed city with rich history).
The driver will give you time to explore these stops independently: Enjoy wandering the streets, shop, grab lunch, gelato, or coffee, and see the iconic landmarks before continuing your journey!
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
Rome - Florence - Venice for Art Lovers (11 nights)
Artistic Italy calls to you!. What can be said about these magnificent cities: Rome (the Eternal City is a living museum and houses untold treasures in the incredible Vatrican Museums), Florence (the capital of Italy’s Tuscany region is home to many masterpieces of Renaissance art and architecture) and Venice (set on gorgeous canals, intimate Gondola rides and under sculpted bridges) that hasn't already been said?. They are home to leading museums, art on every street corner, and a worldwide influence that goes unmatched. There is not enough time to see all the treasures housed in one, let alone three, but that doesn't mean you shouldn't try!.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
Rome - Pompeii - Amalfi with Signature Transfers (6 nights)
Discover rich heritage sites of the Italian capital and other main cities!. Explore historic highlights and consequential neighborhoods of the Eternal City of Rome (with its stunning architecture like the Colosseum and the Roman Forum and delicious food) then take a transfer to Amalfi Town (beautiful small seaside resort, with distinctive architecture, crystal blue waters, and local delicacies), on the scenic Amalfi Coast (known for its stunning coastline, cliffs, and beaches and colorful villages with steep and narrow streets) with a stop in Pompeii.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
The Best of Rome - Florence - Venice plus the Amalfi Coast and Cinque Terre (11 nights)
Along charming places in Italy!. The Eternal City, Rome (with its stunning architecture like the Colosseum and the Roman Forum and delicious food), Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture) and Venice (set on gorgeous canals, intimate Gondola rides under sculpted bridges), have so much to offer, but don't miss out on popular nearby destination: The Amalfi Coast and Cinque Terre (both UNESCO Sites, by the way)!. Visiting the large metropolitan cities is only complemented by visits to the quaint and more authentic collection of villages in these two areas.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat suppor
Includes:
Florence - Tuscany - Italian Riviera with Signature Transfers (8 nights)
Dreamy Italian Tuscany and Riviera!. Combine unforgettable stays at these Tuscany cities: Florence (capital of Tuscany; home to Renaissance Art and Architecture) and Lucca (fantastic medieval city walls that still encircle most of the historic old town); with Santa Margherita Ligure (a charming fishing village) and port city of Genoa (rich cultural heritage encompassing art, music, and culinary traditions) in Italy's Riviera Coast. By private door to door service stops along your way, visit Pisa (world-renowned Leaning Tower), Prato (textil industry, traditional cuisine and wines) and at the Genoese Coast, Castello di Lerici (medieval prison and fortress with spectacular views).
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes: