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Iconic Italian Road Trips: Point of Interest Map
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Iconic Italian Road Trips Vacation Packages

There’s a lot to love about taking an Italy road trip, one of the most beautiful countries in the world that’s best seen from the road and away from the crowds. From north to south and coast to coast, driving in Italy takes you through breathtaking countryside views, incredible mountain scenery, through charming small towns, picturesque seaside vistas, and bustling cities, all with the freedom to define your own adventure.

Best Vacation Packages:

Cities to Explore

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Popular Areas of Italy

  • Cinque Terre

    Cinque Terre means Five Lands (in Italian), and this popular area offers five miles of rocky coast with five small villages (born in the 11th Century as fortresses) overlooking the sea, in the midst of two capes with hundreds of miles of beautiful paths. It offers a unique landscape with twisting coastal footpaths with breathtaking views; beautiful beaches with crystal transparent waters plus old churches, sanctuaries and castles.

  • Umbria and the Hilltowns

    Umbria, the only Italian Region having neither a coastline or a border with other countries, is characterized by hills and historical towns such as Assisi (a World Heritage Site associated with St. Francis of Assisi), Norcia (the hometown of St. Benedict), Gubbio, Spoleto, Todi, Città di Castello, Orvieto, Castiglione del Lago, Narni, Amelia, and other small cities.

  • Tuscany and Hill Towns

    Tuscany is a vibrant, lush and alluring region. From all-time favorite, San Gimignano and Cortona, to lesser known gems like Massa Marittima, Pitigliano and Anghiari, each one has its own distinctive atmosphere. Visitors come to Tuscany for many reasons - Be it the art, the countryside, the food or the wine, there is no shortage of things to see and do. The only question is where to begin.

  • Amalfi Coast And Neapolitan Riviera

    The mild climate, the splendor of the coasts, the richness of its art and history, and the love for food make the Amalfi Coast and Neapolitan Riviera, the fascinating territory that it is. It offers a sea with intense colors and coasts packed with bays, coves and rock faces plus ancient pathways, some of which date back 2,000 years.

  • Italian Lakes

    Adored by romantic poets as well as statesmen and royalty, the beautiful Italian lakes are stunning, with mountains that descend to meet the lakeshore and pretty lakeside towns. They are embedded with fishing villages, medieval castles, Renaissance palazzi and neoclassical villas, ancient ruins, and sumptuous gardens spilling right down the water's edge.

  • Sicily

    One of the pearls of Southern Italy, Sicily is the largest of the Italian islands, just off the "toe" of Italy's "boot." Sicily is rich in UNESCO World Heritage Sites: the archeological area of Agrigento, the famous Valley of the Temples, and Syracuse with the Necropolis of Pantalica. On Sicily’s eastern edge is Mount Etna, one of Europe’s most active volcanoes.

  • Italian Riviera

    The Italian Riviera is a spectacular coastline on the Ligurian Sea extending from the Italian-French border to Capo Corvo, near La Spezia and offering luxuriant mountains to the north and east, and the sapphire blue Mediterranean to the south and west with medieval hilltop hamlets, panoramic vistas, vibrant seaside villages and unspoiled beaches.

See All Popular Areas of Italy

More to Explore

  • Iconic Spanish Road Trips

    With one of the most extensive systems of roads and highways in the world, clocking in at over 10,000 miles, Spain is very easy to traverse by car. Major highways (autopistas and autovías) connect all of Spain`s 45 mainland provinces with one another, and they can be found in the Balearic and Canary Islands as well. Let us help you find your ideal Spanish road trip that`s tailored to your desires.

  • Iconic French Road Trips

    France is not just Paris, but fortified towns with elaborate chateaus and castles; Roman ruins and religious monasteries; verdant vineyards and sunflower fields; magnificent mountains and the warm Riviera sunshine and so much more. With its beautiful winding country lanes, it’s not hard to understand why taking a France road trip tops so many bucket lists around the world.

  • Iconic Croatian Road Trips

    Traveling by car is perhaps the best way to experience everything Croatia has to offer. Our self-drive vacation packages take you where air, train, and ferry simply cannot. Whether you want to explore the Croatian islands, Dalmatia, the Plitvice Lakes, the Kvarner Gulf, Istria, or the nation`s capital, Zagreb, there is at least one great self-drive vacation package that will meet your needs and exceed your expectations. Customize your own Croatia journey by car today!

  • Iconic German Road Trips

    From half-timbered houses and fairytale castles, to dark forests and bustling cities, Germany offers an amazing culture and landscape. The country is large with plenty of adventures to be had and incredible sites to be seen. Driving in Germany is the perfect way to see as much as you possibly can amongst spectacular scenery that will leave you spell bound for more.


  • Beautiful Tuscany (Florence - Lucca - San Gimignano - Siena - Self Drive)
    9 nights from $793*
  • Focus your visit to Italy in wonderful Tuscany!. Visit artistic Florence, then pick up your car and spend some leisurely days staying in Lucca, San Gimignano and Siena to be able to experience all the different aspects of this charming region. Return to Florence for one last stay. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    • Hotel for 2 nights in Florence
    • Rental Car for 6 days
    • Hotel for 2 nights in Lucca
    • Hotel for 2 nights in San Gimignano
    • Hotel for 2 nights in Siena
    • Hotel for 1 night in Florence

  • Cinque Terre - Tuscany - Amalfi with Pompeii
    15 nights from $1,252*
  • Start in with a visit to Genoa, then continue to beautiful Cinque Terre, then visit artistic Florence, after that pick up your car for a stay in Southern Tuscany, then drive to Pompeii for a visit to this incredible insight into Roman times, and finally continue for a stay in the Amalfi Coast. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    • Hotel for 1 night in Genoa
    • Train: Genoa to La Spezia (Cinque Terre)
    • Hotel for 2 nights in Cinque Terre
    • Train: La Spezia (Cinque Terre) to Florence
    • Hotel for 3 nights in Florence
    • Rent a car for 8 days
    • Hotel for 3 nights in Southern Tuscany
    • Hotel for 2 nights in Pompeii
    • Hotel for 3 nights in the Amalfi Coast
    • Hotel for 1 night in Naples
    • Daily breakfast (if stated in hotel description)

  • Cagliari Stay (Self Drive)
    6 nights from $1,689*
  • Visit Cagliari in Sardinia Island of Italy, where all visitors can cherish the coastal views and the resonating culture. The city is best known for being the capital city of the Italian island of Sardinia and is well known for the hilltop Castello, a medieval walled quarter situated high over the rest of the town. Base yourself in Cagliari and explore its beautiful surrounding areas with a rental car. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    • Hotel for 6 nights in Cagliari
    • Rental Car for 7 days

  • Charms of Italy (Venice - Florence - Rome - Sorrento)
    8 nights from $849*
  • Take Italy into your own hands!, with this customizable package combining train transfers and a Rental Car. Start in Venice (sumptuous palaces and romantic waterways), after that, trains will take to Florence (an artists dream: Michelangelo`s David, Botticelli`s Birth of Venus, and Raphael`s La Velata) and Rome (Italy`s treasure with two millennia of artistic achievement). From here, catch your Rental Car and drive along Sorrento (situated on an expansive stretch of cliff, among lemon and olive groves with stunning vistas). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    • Hotel for 2 nights in Venice
    • Train from Venice to Florence
    • Hotel for 2 nights in Florence
    • Train from Florence to Rome
    • Hotel for 2 nights in Rome
    • Rental Car for 3 days
    • Pick Up: Rome Downtown/Drop Off: Naples Airport
    • Hotel for 2 nights in Sorrento
    • Driving Time
      Rome - Sorrento: 3 hrs. 50 mins. approx.
      Sorrento - Naples Airport: 1 hr. approx.

Build Your Own Itinerary

Experience and Adventure

  • UNESCO World Heritage Sites of Italy

    Italy boasts the greatest number of UNESCO World Heritage Sites than any other country in the world. With 51 designated cultural and natural landmarks, it makes up over 5% of UNESCO’s global list. From Dolomites and historic centers of Florence and Rome to Pompeii and the Amalfi Coast, the Italian sites are ideal travel destinations for anyone seeking out history, art, and culture.

  • Italian Wine Regions

    Italy offers the perfect combination of food, wine and people that can’t be beat, and it’s a must for any lover of wine and culture. The country boasts thousands of vineyards found in many of its regions which produce hundreds of famous varieties of wine, from the bold reds in the hills of Tuscany to crisp sparkling wines in the northern lakes region, and one-of-a-kind varietals at rustic island wineries in Sicily.

  • Italian Cuisine

    There’s no greater expression of a culture than the food people eat. It defines a culture, and in Italy, food is life...and food is love. Regional, seasonal and as fresh as possible, Italy’s cuisine is hearty, satisfying and made with heart. Italians are the masters of creating simple dishes that sing with flavor. From haute cuisine to street vendors, Italy’s food is authentic and surprising - pizza and pasta are only the tip of the iceberg when it comes to the diverse array of unforgettable food.


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Cities in Italy

Iconic Italian Road Trips


Cities in Italy

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Italy and Beyond