Italy, a country filled with rich history, stunning landscapes, and vibrant culture, is a dream destination for many travelers. With so much to see and experience, it’s important to plan your trip wisely to make the most of your time. In this article, we’ll explore ten unforgettable itineraries that will take you through some of Italy’s most iconic cities, charming towns, and breathtaking regions. Whether you’re interested in art and history, picturesque landscapes, or delicious cuisine, there’s an itinerary for every type of traveler. So, let’s embark on a virtual journey through Italy and discover the wonders that await!

1. Venice, Florence & Rome by Train

Our first itinerary takes us on a journey through the enchanting cities of Venice, Florence, and Rome. Start your adventure in Venice, known for its romantic canals, exquisite architecture, and vibrant culture. Take a gondola ride along the famous Grand Canal, explore the historic St. Mark’s Square, and visit the iconic Doge’s Palace. Don’t forget to wander through the charming neighborhood of San Polo, where you’ll find hidden gems like artisan studios and local shops.

Next, hop on a train to Florence, the birthplace of the Renaissance. Immerse yourself in the world of art as you visit the renowned Uffizi Gallery and admire masterpieces by Michelangelo, Botticelli, and Leonardo da Vinci. Take a stroll through the Oltrarno neighborhood, known for its artisan workshops and picturesque streets. Finally, make your way to Rome, the eternal city. Marvel at the ancient wonders of the Colosseum, explore the Vatican City, and immerse yourself in the rich history and culture that permeate every corner of the city.

2. The Hill Towns of Tuscany by Car

If you’re seeking a more relaxed and picturesque experience, our second itinerary will take you through the charming hill towns of Tuscany. Rent a car and embark on a journey through the rolling landscapes of this beautiful region. Start in Volterra, a town known for its medieval architecture and alabaster carving. Explore the narrow streets and visit the 12th and 13th-century tower houses that still stand today.

Continue your journey to San Gimignano, famous for its tall towers and panoramic views of the surrounding countryside. Explore the well-preserved medieval streets and savor the local cuisine. Head south to Colle di Val d’Elsa, where you can admire the 13th-century walls and visit the Palazzo Pretorio, which houses artifacts from a nearby Etruscan cemetery.

Make your way to Monteriggioni, a small town surrounded by perfectly preserved 13th-century walls. Take a walk along the walls, visit the fortress, and enjoy the breathtaking views of the Tuscan countryside. Don’t miss the opportunity to explore Siena, a town filled with medieval and Renaissance buildings, including its stunning cathedral. Visit the Museo Archeologico in Asciano to discover more Etruscan artifacts and explore the Olivetan monastery of Monte Oliveto Maggiore.

Conclude your journey in Montalcino, a town that seems frozen in time, with intact walls dating back to the Middle Ages. Walk along the well-preserved walls, visit the castle, and soak in the panoramic views of the Tuscan landscape. Nearby, you’ll find the ancient Abbey of Sant’ √Āntimo, a Romanesque church that is a true architectural gem.

3. Milan to Venice by Train

For art and history enthusiasts, our third itinerary takes you on a train journey from Milan to Venice, passing through some of northern Italy’s most important cultural landmarks. Start your trip in Milan, a fashion capital and home to iconic attractions such as the magnificent Duomo and Leonardo da Vinci’s Last Supper. Explore the historic city center and immerse yourself in the vibrant atmosphere.

As you travel east towards Venice, make a stop in Brescia, a city that preserves its Roman past with impressive remains such as a temple, theater, and forum. If time allows, take a side trip to Desenzano di Garda and enjoy a boat tour of Lake Garda. Continue to Verona, where you can visit the famous Roman arena, Juliet’s house, and explore the beautiful streets of this romantic city.

Next, make your way to Vicenza, renowned for its architecture designed by Andrea Palladio. Visit the Basilica Palladiana, Teatro Olimpico, and the iconic villa La Rotonda. Continue to Padua, where you can’t miss the Shrine of St. Anthony and Giotto’s stunning frescoes in the Cappella degli Scrovegni. Consider a side trip along the Brenta Canal to admire the elegant villas and gardens.

Finally, arrive in Venice, a city like no other. Take a gondola ride along the canals, visit St. Mark’s Square and the Doge’s Palace, and get lost in the maze-like streets of this timeless city. Take your time to savor the unique atmosphere and indulge in the local cuisine.

4. Florence, Prato, Pistoia, Lucca & Pisa by Train or Bus

Our fourth itinerary offers a mix of art, history, and charming towns in Tuscany. Start your journey in Florence, a city renowned for its artistic heritage. Explore the world-class art museums, including the Uffizi Gallery and the Pitti Palace. Take a stroll through the Oltrarno neighborhood and discover its artisan workshops and hidden gems.

Next, visit Prato and Pistoia, two lesser-known towns that offer a glimpse into Tuscany’s rich history. In Prato, marvel at the 15th-century frescoes in the cathedral and explore the historic center. In Pistoia, visit the Cattedrale di San Zeno and admire the 14th-century baptistery.

Continue your journey to Lucca, a town famous for its well-preserved medieval walls and charming atmosphere. Climb the Guinigi Tower for panoramic views and take a leisurely bike ride along the top of the walls. Finally, make your way to Pisa, where you can’t miss the iconic Leaning Tower. Explore the Campo dei Miracoli, a UNESCO World Heritage site, and visit the magnificent cathedral and baptistery.

5. Driving Tour of Sicily

For those seeking a blend of history, natural beauty, and unique culture, our fifth itinerary takes you on a driving tour of Sicily. Start your adventure in Palermo, the capital city, and explore its vibrant markets, historic sites, and stunning architecture. Visit Monreale, home to a magnificent cathedral and breathtaking mosaics.

Head west to Segesta, where you can explore an ancient Greek theater and an unfinished temple. Continue to Trapani, a historic port town with picturesque streets and beautiful views. Don’t miss the nearby hilltop town of Erice, known for its castle and panoramic vistas.

As you travel along the coast, make a stop in Marsala and Mazara del Vallo before reaching Selinunte, home to one of the largest Greek temples in existence. Explore the Valley of the Temples in Agrigento, where you’ll find some of the best-preserved Greek ruins in the world.

Take a detour to Enna to visit the UNESCO World Heritage Site of Villa Romana del Casale, renowned for its well-preserved Roman mosaics. Head south to Ragusa and Modica, two charming towns known for their Baroque architecture. Finally, reach Syracuse, a city filled with ancient Greek theaters, catacombs, and archaeological sites.

6. The Italian Riviera by Train and Boat

Our sixth itinerary takes us along the stunning Italian Riviera, a stretch of coastline dotted with picturesque resorts, fishing villages, and historic treasures. Begin your journey in Sanremo, known as the “flower center” of the Riviera. Explore its beautiful gardens, visit the historic casino, and relax on its pristine beaches.

Make your way to Genoa, a city often overlooked but rich in history and culture. Discover its glorious palaces, churches, and museums, including the famous Genoa Aquarium. Take a boat from Genoa to the postcard-perfect harbor of Portofino, a charming village surrounded by colorful buildings and crystal-clear waters. Continue to Santa Margherita, a perfect base for exploring the surrounding area.

Next, venture to the Cinque Terre, a UNESCO World Heritage Site comprised of five colorful seaside towns perched on rugged cliffs. Explore the charming streets, hike along the coastal trails, and savor the fresh seafood. Conclude your journey in Portovenere, a hidden gem known for its medieval architecture and breathtaking views. Don’t miss the opportunity to visit the nearby islands of Palmaria, Tino, and Tinetto.

7. Lake Garda & the Dolomite Road Driving Tour

Our seventh itinerary combines the beauty of Lake Garda with the stunning landscapes of the Dolomites. Start your journey in Verona, the city of love, and explore its Roman arena, historic castle, and charming streets. Head north to Peschiera, a town located on the southern shore of Lake Garda. Enjoy the lake’s tranquil atmosphere, visit the picturesque village of Sirmione, and take a boat tour to admire the stunning scenery.

Continue along the eastern shore of Lake Garda, stopping in Malcesine to visit its medieval streets and enjoy panoramic views. Reach Riva, a lively town perfect for outdoor activities such as hiking, biking, and sailing. Leave the lake behind and venture into the Dolomites, a UNESCO World Heritage Site known for its dramatic peaks and scenic roads.

Drive through the Sella Pass, a picturesque route that offers breathtaking views of the surrounding mountains. Marvel at the rugged beauty of the Dolomites as you pass through enchanting villages and enjoy the fresh mountain air. Make your way to Vittorio Veneto, a town that showcases the influence of Venetian architecture and history. Before returning to Verona, visit the walled towns of Castelfranco and Citadella.

8. Driving Tour through Emilia-Romagna from Bologna to Florence

Our eighth itinerary takes us through the picturesque region of Emilia-Romagna, from the vibrant city of Bologna to the Renaissance wonders of Florence. Begin your journey in Bologna, known for its medieval towers and beautiful churches. Explore the historic city center, visit the famous Two Towers, and indulge in the local cuisine, including the world-famous Bolognese sauce.

Continue east to Ravenna, a city renowned for its exquisite Byzantine mosaics. Visit the eight churches that house these stunning artworks and immerse yourself in the rich history of this former capital of the Western Roman Empire. Travel along the coast to Cesenatico, a charming fishing village with a floating museum of historic boats.

Head south to Rimini, a city that boasts a rich Roman past. Explore the excavations, the grand Porta Augusto, and the ancient bridge, Ponte Tiberini. Enjoy a leisurely stroll along the beautiful Adriatic beaches if the season is right. Take a side trip to San Marino, a tiny independent republic perched on a hilltop, and explore its historic center and castles.

As you make your way back towards Florence, stop in Forli, a walled town with impressive stone carving at the Abbazia di San Mercuriale. Follow the scenic SS67 road over the Apennines, passing through picturesque villages, before reaching the Renaissance wonders of Florence. Spend your remaining days exploring the city’s art galleries, magnificent architecture, and vibrant streets.

9. Driving Tour of Sardinia

Our ninth itinerary takes us to the stunning island of Sardinia, where pristine beaches, ancient ruins, and unique culture await. Start your journey in Cagliari, the capital city, and visit its main sights, including the ancient citadel and the museum that showcases the island’s unique nuraghe towers.

Head north to see the best-preserved nuraghe on the island, Nuraghe su Nuraxi. Continue west to Oristano and explore the ruins of Tharros, a Phoenician, Carthaginian, and Roman city. Travel along the picturesque coastal road to Bosa, a beautiful town nestled beneath a castle. Enjoy the colorful streets and visit nearby attractions.

Make your way to Alghero, a town known for its Catalan influences and well-preserved historic center. Walk along the city walls and explore the charming stone streets. Take a boat trip to the Grotta di Nettuno, a stunning sea cave with impressive rock formations. Continue to Sassari, where you can discover the local culture and history.

Follow the north coast to Santa Teresa di Gallura and take a ferry to the enchanting Arcipelago di la Maddalena. Explore the pink beaches and crystal-clear waters before reaching the famous Costa Smeralda. Use Arzachena as your base to discover the trendy resort villages and visit the outstanding prehistoric sites.

Drive south along the east coast to Nuoro, a good starting point to explore the mountainous Barbagia region and its remote towns. On your way back to Cagliari, make a stop at Nuraghe Losa and the mysterious well of Santa Cristina. Take your time to enjoy the unique culture, cuisine, and natural beauty that Sardinia has to offer.

10. Driving Tour of the Aosta Valley

Our final itinerary takes us to the scenic Aosta Valley, a stunning region nestled in the Italian Alps. Begin your journey in Turin, a city known for its royal splendor and vibrant culture. Explore the Savoys’ Royal Palace, visit the Mole Antonelliana, and indulge in the city’s culinary delights.

Head north from Turin to the charming village of Breuil-Cervinia, located at the foot of the iconic Matterhorn. Enjoy panoramic views of the mountain, take a cable car ride, and immerse yourself in the alpine atmosphere. On your way back, stop at Lago Blu for a breathtaking view of the Matterhorn’s south face.

Continue your journey in Chatillion and explore the impressive Castle of Fenis, a medieval fortress with stunning frescoes and panoramic views. Arrive in Aosta, the valley’s largest town, and discover its Roman heritage, including the Arch of Augustus and the Roman Theater. Visit the monastic complex of Sant’Orso and admire the mosaics in the cathedral.

Take a cable car to Pila and enjoy panoramic views of the valley and the surrounding Alps. Make a side trip to the Gran Paradiso National Park and explore its beautiful meadows and hiking trails. Conclude your journey in Courmayeur, a chic resort town at the base of Mont Blanc. Visit the Alpine Museum and take a cable car ride to enjoy the incredible views.


Italy offers an endless array of experiences, from the iconic cities of Venice, Florence, and Rome to the charming hill towns of Tuscany, the breathtaking landscapes of the Dolomites, the stunning beaches of Sardinia, and the alpine beauty of the Aosta Valley. Whether you choose to explore the art and history of Italy’s cultural treasures or immerse yourself in the natural wonders and unique culture of its regions, each itinerary promises an unforgettable adventure. So, start planning your trip to Italy and get ready to create memories that will last a lifetime. Buon viaggio!

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Isabella Doherty
Travel junkie. Friend of animals everywhere. Infuriatingly humble explorer. Passionate reader Food practitioner.