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Experience Italy's Finest: 14 Days of Art, History & Beauty


Dates and Prices
Day By Day Itinerary

- Day 1 Welcome to Rome
Ciao Roma! Upon your arrival at the airport, pick up your rental car and settle into your hotel in the heart of Rome.
Suggestion for the day: This afternoon, embark on a leisurely stroll through the city's vibrant streets, soaking in the atmosphere and discovering captivating corners. As the evening descends, savor a delightful Italian dinner at a charming local restaurant, setting the stage for your culinary adventures to come.
- Pro tips:
- If you arrive early enough (before 6 PM), ascend to the tranquil Orange Garden, located on one of Rome's seven hills, for breathtaking city views.
- Take a short walk along Via di Santa Sabina Street to the southwest and reach Piazza dei Cavalieri di Malta. Here, you can peek through the keyhole at the entrance to the Villa dei Cavalieri, revealing a magnificent framed view of St. Peter's Cathedral.
- For convenient exploration, consider using Rome's city buses to avoid parking in busy areas.
- Take some time to discover hidden restaurant gems near your location.
- Pro tips:
- Day 2Rome
Suggestions for the day: Discover Ancient Rome and the Vatican City
- In the morning we recommend exploring Vatican City. Make sure to visit the Vatican Museums, the Sphere within a Sphere sculpture, the breathtaking Sistine Chapel, and the awe-inspiring St. Peter's Basilica.
- Take a short walk to Castel Sant'Angelo before crossing the Tiber River and venturing into the heart of Ancient Rome. If you'd like further guidance, consider booking an afternoon tour of the Colosseum and Roman Forum. Spend the rest of your day exploring iconic landmarks like the Trevi Fountain, the Pantheon, sipping an espresso in Piazza Navona, and climbing the Spanish Steps. If you missed the Orange Garden yesterday, be sure to include it in your explorations today.
- Day 3Drive to Positano
Suggestions for the day: Explore the Ruins of Pompeii and Sorrento
- In the morning start your journey to Pompeii. To reach Pompeii from Rome, you’re looking at a 2-hour, 40-minute drive. There you can witness the devastation caused by the eruption of Mount Vesuvius and walk around this city frozen in time. Stay the night in Positano and, on your way there, you can stop and explore the beautiful Sorrento. Here are our suggestions for places to see in Sorrento:
- The Museo della Tarsia Lignea - inlaid Wood Museum
- Museo Correale di Terranova - archaeological finds, paintings, prestigious porcelain.
- Corso Italia - fashionable shops and boutiques
- Piazza Tasso - aperitivo and people-watch
- Vallone dei Mulini - see the ruins of a water-powered mill
- Villa Fiorentino - exhibitions are often held here
- Villa Comunale - Bay of Naples and Vesuvio views
- Cloister of San Francesco - a Medieval cloister dating from the 1300's
- Basilica di Sant'Antonino - dedicated to the city's patron saint
- The Lanes of the Historic Center - historic streets in Sorrento with artisan workshops
- Sedil Dominova - frescoed cupola
- Marina Grande - Sorrento's fishing village
- Bagni della Regina Giovanna - a flight of stairs down to Roman ruins in a small lagoon
- Pro Tips:
- Have some cash/ change on you to pay road tolls as some don’t accept credit/ debit cards.
- Pay attention to speed limits, and radars on the motorways.
- In the morning start your journey to Pompeii. To reach Pompeii from Rome, you’re looking at a 2-hour, 40-minute drive. There you can witness the devastation caused by the eruption of Mount Vesuvius and walk around this city frozen in time. Stay the night in Positano and, on your way there, you can stop and explore the beautiful Sorrento. Here are our suggestions for places to see in Sorrento:
- Day 4Positano
Suggestions for the day: A Day on the Isle of Capri
- On this day we suggest you visit the Isle of Capri. You will cross the Bay of Naples and enjoy the beautiful sights. Capri is a picturesque island located in the Tyrrhenian Sea off the Sorrentine Peninsula, on the south side of the Gulf of Naples in Italy. Known for its stunning natural beauty and glamorous atmosphere, Capri has been a favorite destination among artists, writers, and celebrities for centuries. The island is famed for its crystal-clear waters, rugged coastline, and dramatic landscapes, inspiring many works of art throughout history. You can explore ancient ruins, charming villages, and upscale boutiques while enjoying the island's laid-back Mediterranean lifestyle. Whether you're looking for relaxation or adventure, Capri Island offers something for everyone. Later, you will return to the mainland and spend the night in Positano.
- Day 5Drive to Assis
Suggestions for the day: Explore the Mystical Town of Assis and/or Tivoli
Start your way back north with a stop at the historic Benedictine Abbey of Cassino, a significant World War II battleground. Afterward, you have a captivating choice:
- Option 1: Journey northward to the enchanting town of Assisi, St. Francis's birthplace. Explore the Basilica of St. Francis, immerse yourself in the town's history, and experience its timeless allure.
- Option 2: If you desire a detour closer to Rome, venture to Tivoli and immerse yourself in the splendor of its villas and gardens. Discover archaeological ruins, medieval cathedrals, and the unforgettable Villa d'Este Gardens.
- Pro tips for your stop in Tivoli:
- Explore Tivoli's archaeological ruins and historical villas (for some you have to pay for entrance fee).
- Experience the divine presence in the town's medieval cathedrals.
- Head to the Villa d'Este Gardens to see unforgettable gardens.
- Check out Rocca Pia, an ancient 15th-century fortress built to protect Tivoli.
- Enjoy the finest Italian cuisine at the Ristorante Osteria la Briciola and other top-rated restaurants in Tivoli.
- Day 6Drive to Venice
Suggestions for the day: Journey to Venice through Emilia Romagna
- Begin your day with a scenic drive through the breathtaking countryside of Emilia Romagna, a region renowned for its culinary prowess. Indulge your tastebuds with stops in cities like Bologna, Ravenna, Parma, or Modena – the birthplace of tortellini, mortadella, and parmesan cheese. We especially recommend exploring Parma, where you can delve into the rich traditions of cheese, ham, and balsamic vinegar production. In the afternoon, continue your journey towards Venice and settle into your hotel for the evening.
What to Know Before Visiting Venice:
- Cars are not allowed to be driven into Venice. That’s why Venice offers numerous car parks where you can leave your car even for long periods, at a reasonable charge. There is a parking at Piazzale Roma, at the end of the road into Venice; one at Tronchetto, to the right at the end of the bridge into Venice; and reasonably priced parking next to the train station at Mestre, on the mainland. From Piazzale Roma or Tronchetto, you can take a vaporetto (water bus) to other parts of Venice. From Mestre, you can take a train to Santa Lucia station or a bus to Piazzale Roma, then a vaporetto. Most properties offer transfers from the car parks or bigger terminals. However, guests must contact the property with arrival details before travel. All transfers must be booked in advance.
- On certain dates of the year, visitors must pay an access fee of EUR 5 per person per day to enter Venice. Those with accommodation in Venice are exempt from paying this. Guests must however request an exemption voucher in advance and present it with an identity document on arrival. To check affected dates and request an exemption, visit cda.comune.venezia.it.
- Day 7Venice
Suggestions for the day: Discover Venice
- Prepare to be enchanted by Venice! Experience the artistry of traditional glassblowing, browse for souvenirs, and navigate the picturesque canals. Your itinerary should undoubtedly include the awe-inspiring St. Mark's Square and Basilica, the historic Bridge of Sighs, and the magnificent Doge's Palace. Consider a gondola ride for a romantic touch or indulge in Venetian delicacies at a cozy bacaro, starting with the refreshing Venetian Spritz.
- Pro tip: If you wish to book any tours and experiences in Venice, do so in advance.
- Day 8Drive to Lake Maggiore
Suggestions for the day: On to Milan and Scenic Lake Maggiore
- Journey westward to Verona (approximately 1 hour and 20 minutes), home to Shakespeare's Romeo and Juliet. Explore the Roman arena and Juliet's Balcony before continuing to the fashion and design capital of Italy - Milan (from Verona 2h drive). Here, explore the Gothic Duomo, La Scala Opera House, and the iconic Galleria Vittorio Emanuele II. In the late afternoon, venture towards stunning Lake Maggiore (1 hour 45 min drive) for a relaxing overnight stay.
- Pro-tip for Verona: Utilize the Porta Palio or Piazzale Guardini car parks for free parking within walking distance to the center.
- Day 9Lake Maggiore
Suggestions for the day: Lake Como and Island Excursions
- Embrace the serenity of Lake Como (from Lake Maggiore 1h30min drive). Spend the day unwinding amidst its picturesque landscapes, indulge in delicious gelato, and perhaps embark on a scenic cruise. Later, consider indulging in a memorable dining experience infused with local flavors at one of the lakeside villas – the historic Villa Toscanini, a former hideaway of the legendary conductor Arturo Toscanini, is an exceptional choice.
- Day 10Drive to Portofino
Suggestions for the day: Genoa and Picturesque Portofino
Depending on your interests, tailor your day to one of these options:
- Option 1: Drive towards Genoa (approximately 3 hours) and explore the vibrant city's port, aquarium, Galata Maritime Museum, and Biosfera tropical garden. Afterward, continue to the charming coastal town of Portofino (2 hours) for a relaxing evening.
- Option 2: Embark on a direct journey to Portofino (approximately 3 hours and 30 minutes) for a full day of coastal relaxation and exploration.
- Day 11Drive to Florence
Suggestions for the day: Pisa, Cinque Terre & Florence
Today offers another exciting choice with three tempting possibilities:
- Option 1: Drive straight to Pisa, home of the iconic Leaning Tower, and immerse yourself in its Square of Miracles.
- Option 2: Detour the enchanting villages of Cinque Terre, nestled along the rugged coastline, before reaching Pisa.
- Option 3: Travel to the marble quarries of Carrara for a unique experience before admiring the Leaning Tower in Pisa.
Finally, make your way to Florence, the 'Cradle of the Renaissance', for an approximately 1.5-hour drive.
- Day 12Florence
Suggestions for the day: Art and Architecture in Florence
- Dive into the artistic heart of Florence. Explore renowned galleries, learn traditional pasta-making techniques, or uncover the stories behind the city's historic leather and gold industries. Remember, Florence was the home of the influential Medici family, whose artistic and architectural legacy surrounds you. Ascend to Piazzale Michelangelo for breathtaking panoramic views of the city skyline, highlighted by the elegant Duomo and the historic Ponte Vecchio.
- Day 13Drive to Rome
Suggestions for the day: Treasures of San Gimignano and Return to Rome
- Venture south towards Rome with a captivating stop in San Gimignano, a Tuscan hill town celebrated for its medieval towers and rich history. Explore the Piazza del Duomo, surrounded by these architectural marvels and 13th-century city walls. For fans of the film The Gladiator, parts were filmed in the scenic Orcia Valley (Val d'Orcia,) a picturesque detour option. Enjoy a final delightful dinner in Tuscany or back in Rome.
- Day 14Farewell Italy
Farewell, Italy! As your Italian adventure concludes, return your rental car and bid farewell to Rome. Reflect on the unforgettable memories created as you embark on your journey home. We hope you had an extraordinary time and look forward to welcoming you back for another adventure soon.
Why We Love This Deal
- Explore at Your Own Pace: This road trip itinerary puts you in the driver's seat, allowing you to craft your own Italian adventure. Linger in charming towns, detour to scenic vistas, and discover hidden gems along the way.
- Uncover Iconic Destinations: Our carefully planned route guides you through Italy's must-see destinations. Explore Pompeii's ancient ruins, soak in the beauty of Capri and the Amalfi Coast, marvel at Venice's canals, and delve into Florence's artistic treasures.
- Culinary Freedom: Savor Italy's incredible cuisine on your own terms. Stop at family-run trattorias, sample regional specialties in bustling markets, or simply pack a picnic and enjoy the stunning scenery.
- Personalized Adventure: With a rental car, you have the freedom to customize your itinerary on the fly. Follow your interests, whether they lead you to historic towns, scenic lakes, or off-the-beaten-path villages.
- Incredible Value: We've designed this road trip to provide maximum flexibility and fantastic value. From carefully selected routes to suggested activities, this package gives you the tools to create an unforgettable journey at your own pace.
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