15-Night Italy Road Trip Itinerary

Day 1: Arrival in Rome – Transfer to Milan

Morning: Arrive at Rome Fiumicino Airport and pick up your rental car. Begin your journey by driving north to Milan, approximately 6 hours of scenic highway drive.

Afternoon: After arrival in Milan, check into your hotel and visit the Milan Cathedral (Duomo di Milano) and Galleria Vittorio Emanuele II for an elegant introduction to the city.

Evening: Enjoy a relaxed dinner in the Brera District, known for its vibrant atmosphere and exquisite restaurants.

Day 2: Milan Exploration

Morning: Explore the Sforza Castle and visit the spectacular Santa Maria delle Grazie, home of Leonardo da Vinci’s Last Supper (advance booking recommended).

Afternoon: Spend the afternoon at the Pinacoteca di Brera art gallery and stroll through the fashionable streets of Via Montenapoleone.

Evening: Experience Milanese nightlife with an aperitivo in the Navigli district.

Day 3: Milan to Tuscany (Chianti Region)

Morning: Drive from Milan to Tuscany, checking into a countryside villa near Greve in Chianti. The trip is around 4.5 hours via car.

Afternoon: Explore the Chianti wine region with visits to renowned vineyards and wine tastings.

Evening: Enjoy a traditional Tuscan dinner at the villa or a local trattoria surrounded by rolling hills.

Day 4: Tuscany – Florence Day Trip

Morning: Drive about 1 hour to Florence and start at the iconic Florence Cathedral (Duomo) and Piazza della Signoria.

Afternoon: Visit the Uffizi Gallery and Ponte Vecchio, immerse in Renaissance art and architecture.

Evening: Return to your Tuscan accommodation or enjoy dinner in Florence before heading back.

Day 5: Tuscany to Naples

Morning: Depart early and drive approximately 6 hours to Naples. Check-in and relax after the scenic coastal journey.

Afternoon: Explore Naples’ historic center, including Spaccanapoli and the Naples National Archaeological Museum.

Evening: Try authentic Neapolitan pizza at a famous pizzeria such as Da Michele.

Day 6: Naples & Day Trip to Pompeii

Morning: Short drive (about 30 minutes) to the Pompeii Archaeological Site for a half-day guided tour.

Afternoon: Return to Naples, then visit the Castel dell'Ovo and stroll along the seafront.

Evening: Enjoy a seaside dinner with views of Mount Vesuvius.

Day 7: Naples to Capri

Morning: Drive to Pier 7 in Naples for a ferry crossing to Capri, approximately 45 minutes. Park your car in Naples, as Capri is car-free.

Afternoon: Explore Piazzetta di Capri, visit the Blue Grotto, and enjoy the island's charming streets.

Evening: Dine overlooking the sea and stay overnight on Capri.

Day 8: Capri to Amalfi Coast (Positano & Amalfi)

Morning: Take a ferry from Capri to Positano (about 30 minutes). Pick up your rental car on the mainland for coastal exploration.

Afternoon: Drive along the scenic Amalfi Coast, stopping in Positano for shopping and beach time, then continue to Amalfi (approx. 40 minutes).

Evening: Stay overnight in Amalfi and savor fresh seafood in a cliffside restaurant.

Day 9: Amalfi to Puglia (Lecce area)

Morning: Depart Amalfi early for a long but beautiful drive (approx. 5.5 hours) to the Puglia region, staying near Lecce.

Afternoon: Explore Lecce’s baroque architecture including the Basilica di Santa Croce.

Evening: Enjoy traditional Puglian cuisine in the historic center.

Day 10: Puglia Day Exploration

Morning: Drive to the stunning Alberobello to see the famous Trulli houses.

Afternoon: Visit Polignano a Mare for dramatic coastline views and relaxed cafes.

Evening: Return to Lecce area and indulge in local wines and cuisine.

Day 11: Puglia to Rome

Morning: Start your journey back to Rome (approx. 5.5-hour drive). Arrive and check into your hotel.

Afternoon: Take a relaxing walk around Piazza Navona and visit the Pantheon.

Evening: Dinner in the Trastevere neighborhood known for its lively atmosphere.

Day 12: Rome Ancient Highlights

Morning: Visit the Colosseum and Roman Forum, immerse yourself in ancient history with a guided tour.

Afternoon: Explore Palatine Hill and Capitoline Museums.

Evening: Walk to Trevi Fountain and enjoy gelato nearby.

Day 13: Vatican City

Morning: Visit St. Peter's Basilica and the Vatican Museums, including the Sistine Chapel (book tickets in advance).

Afternoon: Relax at Borgo Pio or take a stroll along the Tiber River.

Evening: Dine in the elegant Prati district.

Day 14: Rome Leisure Day

Morning: Explore Villa Borghese and the Borghese Gallery, enjoy a peaceful park atmosphere.

Afternoon: Shopping in Via del Corso or visit the Spanish Steps.

Evening: Farewell dinner in a traditional Roman osteria.

Day 15: Departure from Rome

Morning: Return your rental car at Rome Fiumicino Airport and prepare for your flight home.

Afternoon: Depending on your flight time, enjoy last-minute sightseeing or shopping near the airport.

Evening: Departure.

Time and Cost Estimates

• Milan Cathedral & Galleria Vittorio Emanuele II: 3 hours, €20
• Leonardo da Vinci’s Last Supper: 2 hours, €15
• Chianti Wine Tastings: 4 hours, €50
• Florence Uffizi Gallery: 3 hours, €25
• Pompeii Archaeological Site: 4 hours, €18
• Capri Blue Grotto Tour: 2 hours, €14
• Amalfi Coast Exploration: Full day, free to €30 for parking and minor fees
• Alberobello Trulli Houses Visit: 3 hours, €10
• Rome Colosseum & Roman Forum: 4 hours, €18
• Vatican Museums & Sistine Chapel: 4 hours, €30
• Rental Car (15 days): Approx. €900 including fuel and tolls
• Ferries (Naples-Capri, Capri-Amalfi): Approx. €40 total
• Accommodation (avg €120/night x 15 nights): €1,800
• Total Estimated Cost: €3,170

Tips

If you prefer a shorter trip, consider focusing on fewer regions such as Tuscany, Florence, and Rome, reducing long drives and allowing more time to soak in each location. For more immersion, extend your stay in the Amalfi Coast or Puglia to explore hidden gems and relax longer. Adjust your itinerary according to personal interests and travel pace, but the car-based approach offers great flexibility to experience Italy’s diverse landscapes.