By A road trip through Italy offers an unrivaled opportunity to explore the country’s stunning landscapes, historic cities, and vibrant culture. From the art and history of Rome to the picturesque coastal towns of the Amalfi Coast, this 14-day itinerary covers the best of Italy’s diverse regions. Along the way, you’ll experience charming towns, ancient ruins, and breathtaking vistas that make Italy a dream destination for travelers seeking adventure and relaxation.
Overview
Trip Length: 14 Days
Start/End: Rome
Total Distance: 1,500 miles (2,400 km)
Transportation: Rental car (with optional train rides and ferry rides)
Best For: First-time visitors, couples, photographers, and culture lovers
Regions Covered: Lazio, Tuscany, Veneto, Lombardy, and Campania
14-Day Italy Road Trip Itinerary
Day 1: Arrival in Rome – Ancient Wonders and City Vibes
Your Italian adventure kicks off in Rome, where history comes alive at every corner. Begin with a visit to the Colosseum, followed by a stroll through the Roman Forum and Palatine Hill. Don’t miss the Trevi Fountain—legend has it that tossing a coin guarantees your return to Rome. End your day with a visit to the Pantheon and Piazza Navona.
Things to Do:
- Explore the Colosseum, Roman Forum, and Palatine Hill
- Visit the Pantheon and Piazza Navona
- Enjoy cacio e pepe in Trastevere
- Grab gelato near Campo de’ Fiori
Evening Tip: Head to Trastevere for dinner and drinks, where the vibrant atmosphere sets the stage for the journey ahead.
Day 2: Rome Continued – The Vatican and Hidden Corners
Start your day with a visit to the Vatican Museums, home to Michelangelo’s Sistine Chapel. Don’t miss the chance to climb to the top of St. Peter’s Basilica for panoramic views of the city. In the afternoon, explore the quieter streets of Rome, like Piazza Navona and the Aventine Keyhole, where you can get a perfect view of St. Peter’s through a tiny peephole.
Things to Do:
- Visit the Vatican Museums and Sistine Chapel
- Climb St. Peter’s Basilica
- Explore Piazza Navona and Campo de’ Fiori
- Discover the Aventine Keyhole viewpoint
Evening Tip: Enjoy the sunset from Pincio Terrace and have dinner at a rooftop trattoria.
Day 3: Rome → Florence – The Renaissance Awakens
After breakfast, pick up your rental car or take a train to Florence, Tuscany’s Renaissance capital. The drive offers scenic views of rolling hills and vineyards. Once in Florence, head straight for the Uffizi Gallery to see works by Botticelli and da Vinci. Then, take a walk across the Ponte Vecchio, where the Arno River sparkles in the golden hour light.
Things to Do:
- Climb the Florence Duomo
- Visit the Uffizi and Accademia Galleries
- Walk across the Ponte Vecchio
- Explore Piazza della Signoria
Evening Tip: Try a traditional bistecca alla fiorentina paired with Chianti wine, and take a leisurely stroll through the city at night.
Day 4: Tuscany Day Trip – Vineyards, Villages, and Views
Today, take a road trip through the Tuscan countryside. Start with a visit to Siena, known for its Gothic architecture and Piazza del Campo. Then, continue to San Gimignano, a hilltop town famous for its medieval towers and delicious gelato. If time allows, head to the Chianti region for wine tastings.
Things to Do:
- Explore Siena’s Piazza del Campo
- Visit San Gimignano’s towers and artisan shops
- Wine tasting in Chianti
- Walk through the medieval village of Monteriggioni
Evening Tip: Return to Florence and watch the sunset from Piazzale Michelangelo for stunning views of the city.
Day 5: Florence → Venice – The City of Canals
Drive or take the train to Venice, a city unlike any other. Once there, park outside the city and take a vaporetto (water bus) to explore Venice’s iconic canals. Stroll through St. Mark’s Square, visit the Doge’s Palace, and cross the Rialto Bridge.
Things to Do:
- Visit St. Mark’s Basilica and Doge’s Palace
- Ride the Grand Canal by vaporetto
- Explore the Rialto Market
- Wander through lesser-known districts like Dorsoduro
Evening Tip: Take a romantic gondola ride and enjoy dinner along the canal.
Day 6: Venice Islands – Burano, Murano & Torcello
Escape the crowds and visit the colorful islands of Murano, Burano, and Torcello. Murano is famous for glassmaking, Burano for its brightly painted houses, and Torcello for its historical serenity. These islands offer a quieter, more authentic side of Venice.
Things to Do:
- Watch glass-blowing in Murano
- Stroll through Burano’s colorful lanes
- Visit Torcello’s ancient basilica
- Stop by Libreria Acqua Alta, Venice’s unique floating bookstore
Evening Tip: Head back to Venice for a peaceful dinner by candlelight.
Day 7: Venice → Lake Como – Alpine Serenity
Depart Venice and drive toward Lake Como, nestled at the foot of the Alps. Stop in Verona to see Juliet’s Balcony before arriving at the lake. Lake Como’s serene beauty is the perfect antidote to the hustle and bustle of the cities. Take a ferry between Bellagio, Varenna, and Menaggio to explore charming lakeside villages.
Things to Do:
- Take a ferry between Bellagio, Varenna, and Menaggio
- Visit Villa del Balbianello and Villa Carlotta
- Hike the Greenway del Lago di Como
- Enjoy gelato in Bellagio
Evening Tip: Dine lakeside at La Darsena as the mountains reflect in the water.
Day 8: Lake Como – Hidden Gems & Relaxation
Spend another day at Lake Como, exploring its quiet coves and picturesque villages. Hike the Sentiero del Viandante trail for spectacular views or take a cable car to Brunate for panoramic vistas of the lake and surrounding mountains.
Things to Do:
- Hike the Sentiero del Viandante trail
- Visit Nesso Waterfall
- Ride the cable car to Brunate
- Explore Como Town’s cathedral and boutiques
Evening Tip: Toast to northern Italy with prosecco as the sun sets over the lake.
Day 9: Lake Como → Amalfi Coast – Travel Day
Today is a travel day as you make your way to the Amalfi Coast. Take a train or flight to Naples and pick up another rental car for the coast. As you drive down toward the sea, the landscape transforms into jagged cliffs, pastel villages, and lemon groves.
Evening Tip: Settle in at Positano or Sorrento, enjoy a seafood dinner, and watch the sunset over the Mediterranean.
Day 10: Amalfi Coast – Positano, Amalfi & Atrani
Start your day with a drive along the Amalfi Coast, one of the most scenic routes in the world. Begin in Positano, where colorful houses spill down the cliffs, then visit Amalfi to see its cathedral, and end the day in the quiet village of Atrani.
Things to Do:
- Explore Positano’s boutiques and cafés
- Visit Amalfi Cathedral
- Walk to Atrani’s beach
- Stop for photos at Furore Fjord
Evening Tip: Enjoy a romantic dinner at Le Sirenuse in Positano.
Day 11: Ravello – Gardens, Views, and Music
Make your way to Ravello, a tranquil town perched above the coast. Visit the stunning Villa Rufolo and Villa Cimbrone, whose Terrace of Infinity offers one of the best views in Italy. Take a stroll through Ravello’s charming streets or attend a classical concert if you’re visiting in summer.
Things to Do:
- Explore Villa Rufolo and Villa Cimbrone
- Attend a classical concert (in summer)
- Visit Minori or Scala
- Try lemon pastries at Sal De Riso in Minori
Evening Tip: Stay overnight in Ravello for a peaceful night under the stars.
Day 12: Capri Island – The Jewel of the Mediterranean
Take a ferry from Amalfi or Sorrento to Capri, one of Italy’s most glamorous islands. Visit the Blue Grotto, take the chairlift to Monte Solaro, or hike the Pizzolungo Trail for stunning sea views.
Things to Do:
- Visit the Blue Grotto and Anacapri
- Take the chairlift to Monte Solaro
- Hike the Pizzolungo Trail
- Shop or dine in Capri Town
Evening Tip: Watch the sunset over the Faraglioni rocks from Da Luigi ai Faraglioni.
Day 13: Sorrento & Pompeii – Ancient History and Coastal Charm
On your penultimate day, explore the ancient ruins of Pompeii, preserved by volcanic ash for centuries. Then, drive up to Mount Vesuvius for panoramic views of the Bay of Naples. In the evening, relax in Sorrento with dinner by the water.
Things to Do:
- Explore the ruins of Pompeii
- Hike Mount Vesuvius
- Visit Sorrento’s old town and Marina Grande
- Try fresh seafood pasta
Evening Tip: Celebrate your last night with a meal at Grand Hotel Excelsior Vittoria.
Day 14: Return to Rome – Farewell to Italy
Your journey ends with a drive back to Rome. If you have time, stop at Civita di Bagnoregio, a fairytale village perched on a cliff. Reflect on your adventure over one last espresso in Rome before heading to the airport.
Final Thoughts
A 14-day road trip through Italy offers an incredible chance to experience the country’s rich history, stunning landscapes, and lively culture. From the art-filled streets of Florence to the peaceful shores of Lake Como, every moment is a reminder of why Italy remains one of the world’s top travel destinations. Take your time, explore the unexpected, and savor every second of this unforgettable journey.
