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:
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9 nights from $1,482*More details›
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Cities to Explore
Popular Areas of Italy
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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.
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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.
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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.
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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.
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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.
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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.
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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.
More to Explore
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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.
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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.
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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!
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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.
SUGGESTED ITINERARIES
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Beautiful Tuscany Self Drive (Florence - Lucca - San Gimignano - Siena)9 nights from $1,571*› - Flight into and out of Florence
- 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
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Rail to Road: Genoa - Cinque Terre - Florence - Southern Tuscany - Amalfi Coast11 nights from $1,882*›
- Flight into Genoa and out of Naples
- Hotel for 2 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
- Rental car for 5 days
- Hotel for 2 nights in Southern Tuscany
- Hotel for 2 nights in the Amalfi Coast
Driving Time
Southern Tuscany- Amalfi Coast: 6 hrs. approx.-
Cagliari Stay (Self Drive)6 nights from $2,220*›
- Flight into and out of Cagliari
- Hotel for 6 nights in Cagliari
- Rental Car for 7 days
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Rail to Road: Charms of Italy (Venice - Florence - Rome - Sorrento)8 nights from $1,299*›
- Flight into Venice and out of Naples
- 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.
Easily upgrade your vacation to include guided activities with our Experience Series package
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Experience and Adventure
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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.
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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.
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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.
Italy Customer Reviews
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An email sent out 2 weeks prior to trip would be nice, letting us know the email with travel details would be coming a week prior to the actual trip w ...Traveled on: 10/11/2026
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Everything was great, the hotels were very nice and centrally located and within walking distance to all the must see attractions in Rome, Florence an ...Traveled on: 10/7/2026
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The trip was great besides all of the trains in between cities left so early in the day that we only got 1 whole day in each city. Would have preferre ...Traveled on: 10/4/2026
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Let me think about that and get back to you with some useful information ...Traveled on: 9/30/2026
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Transportation was great! Hotels were fine, but you need to give them contact information! They all told me they had no way to reach out to me, aski ...Traveled on: 9/29/2026