Try This 14 Day Italy Road Trip Itinerary Planner

Italy isn’t just a destination, it’s an experience that unfolds with every turn of the road. Between its ancient cities, Renaissance masterpieces, and cliffside villages clinging to turquoise seas, Italy invites you to slow down, explore deeply, and savor life moment by moment.

This 14-day Italy road trip itinerary was designed to give travelers the perfect blend of culture, coastlines, and countryside. It combines the best of Rome, Florence, Venice, Lake Como, and the Amalfi Coast, with time to relax, wander, and truly feel Italy’s rhythm.

From floating through Venice’s canals to watching the sunset over Positano, this journey takes you through the heart and soul of Italy, one unforgettable drive at a time.

Overview

• Trip Length: 14 Days
• Start/End: Rome
• Total Distance: 1,500 miles (2,400 km)
• Transportation: Rental car + optional train segments + ferry rides
• Best For: First-time visitors, couples, photographers, and cultural travelers
• Regions Covered: Lazio, Tuscany, Veneto, Lombardy, and Campania

14-Day Italy Road Trip Itinerary

Day 1 – Arrival in Rome: Ancient Wonders and La Dolce Vita

Your Italian adventure begins in Rome, the Eternal City. Once you’ve checked into your hotel, take your first stroll through streets steeped in history — where ancient ruins rise beside buzzing cafés and the aroma of espresso fills the air. Start your exploration at the Colosseum, the city’s most iconic landmark, before wandering through the Roman Forum and up Palatine Hill, where emperors once ruled.

Later, toss a coin into the Trevi Fountain, legend says it guarantees your return, and admire the timeless symmetry of the Pantheon.

Things to Do:

• Explore the Colosseum, Forum, and Palatine Hill
• Visit the Pantheon and Piazza Navona
• Enjoy cacio e pepe in Trastevere
• Grab gelato near Campo de’ Fiori

Evening Tip: End your first night in Trastevere, where string lights, cobblestones, and live music set the tone for the adventure ahead.

Day 2 – Rome Continued: The Vatican and Hidden Corners

Start early to visit the spiritual heart of Italy — Vatican City. Tour the Vatican Museums and admire the frescoes of the Sistine Chapel, then climb the dome of St. Peter’s Basilica for panoramic views of the city.

In the afternoon, wander through Piazza Navona, Campo de’ Fiori, and the quieter corners of Rome. Don’t miss the Aventine Keyhole, where you’ll see St. Peter’s framed perfectly through a hidden peephole.

Things to Do:

• Tour Vatican Museums & Sistine Chapel
• Climb St. Peter’s Basilica
• Explore Piazza Navona & Campo de’ Fiori
• Visit the Aventine Keyhole viewpoint

Evening Tip: Watch the sunset from Pincio Terrace overlooking Piazza del Popolo before dinner at a rooftop trattoria.

Day 3 – Rome → Florence: The Renaissance Awakens

After breakfast, pick up your rental car or take the fast train to Florence, Tuscany’s Renaissance capital. The drive north is smooth and scenic, passing cypress-lined hills and vineyards. Upon arrival, the city’s skyline greets you — dominated by the red dome of Santa Maria del Fiore.

Spend the afternoon exploring the Uffizi Gallery, home to masterpieces by Botticelli and da Vinci. Then, cross the Ponte Vecchio and watch the Arno River shimmer at golden hour.

Things to Do:

• Climb the Florence Duomo
• Visit the Uffizi and Accademia Galleries
• Walk the Ponte Vecchio
• Explore Piazza della Signoria

Evening Tip: Try a traditional bistecca alla fiorentina paired with Chianti wine and stroll through the city under glowing street lamps.

Day 4 – Tuscany Day Trip: Vineyards, Villages, and Views

Florence is the gateway to Tuscany, and today’s drive through its countryside is a dream come true for anyone who loves winding roads, vineyard views, and medieval towns. Begin in Siena, a UNESCO-listed gem where Gothic architecture and the Palio horse race define local pride. Then continue to San Gimignano, known for its stone towers and award-winning gelato.

If time allows, detour through the Chianti region, where rolling vineyards and wineries invite you for tastings of Sangiovese wines and olive oils.

Things to Do:

• Stroll through Siena’s Piazza del Campo
• Visit San Gimignano’s towers and artisan shops
• Wine tasting in Chianti Classico
• Explore the walled village of Monteriggioni

Evening Tip: Return to Florence and watch the sunset from Piazzale Michelangelo, where the whole city glows beneath you.

Day 5 – Florence → Venice: The City of Canals

The drive (or train) to Venice takes about three hours and introduces you to northern Italy’s landscapes. Upon arrival, park your car outside the city and glide in on a vaporetto — Venice is entirely car-free. The first glimpse of the Grand Canal, lined with marble palaces and bridges, feels like stepping into a painting.

Spend your afternoon wandering St. Mark’s Square, exploring the Doge’s Palace, and crossing the Rialto Bridge. Venice is a labyrinth meant to be lost in — every corner hides charm, from artisan shops to quiet courtyards.

Things to Do:

• Visit St. Mark’s Basilica and Doge’s Palace
• Ride the Grand Canal by vaporetto
• Stroll the Rialto Market
• Explore lesser-known districts like Dorsoduro

Evening Tip: Take a gondola ride at twilight and dine along the canal at Osteria Enoteca Ai Artisti.

Day 6 – Venice Islands: Burano, Murano & Torcello

Escape the bustle of central Venice and discover its colorful lagoon islands. Murano is famous for glassmaking — you can watch artisans blowing molten glass into shimmering art. Burano enchants with rainbow-painted homes and delicate lacework, while Torcello offers serenity and ancient history.

These islands showcase a slower, more local side of Venetian life — perfect for photographers and daydreamers alike.

Things to Do:

• Watch glass-blowing in Murano
• Explore Burano’s colorful lanes
• Visit Torcello’s ancient basilica
• Stop by Libreria Acqua Alta, Venice’s floating bookstore

Evening Tip: Return to the city for a peaceful dinner by candlelight — Venice after dark is pure magic.

Day 7 – Venice → Lake Como: Alpine Serenity

Depart Venice and head northwest toward Lake Como, nestled in the foothills of the Alps. The drive passes through Verona (worth a short stop for Juliet’s Balcony) before reaching the shimmering waters of Como.

Lake Como feels worlds away — tranquil, elegant, and surrounded by peaks that change color with the light. Take a ferry between Bellagio, Varenna, and Menaggio, exploring cobbled streets, lakefront cafés, and historic villas.

Things to Do:

• Ferry hop between Bellagio, Varenna & Menaggio
• Visit Villa del Balbianello and Villa Carlotta
• Walk the Greenway del Lago di Como trail
• Enjoy gelato on the promenade in Bellagio

Evening Tip: Dine lakeside at La Darsena, where the mountains reflect in the water at sunset.

Day 8 – Lake Como: Hidden Gems & Relaxation

Spend another day soaking in the calm beauty of Lake Como. Take a morning boat out to secluded coves, hike the scenic Sentiero del Viandante trail, or visit the village of Nesso with its photogenic waterfall.

In the afternoon, relax with coffee in Varenna’s Piazza San Giorgio and enjoy the slower pace — the lake invites you to linger.

Things to Do:

• Hike Sentiero del Viandante or take a boat tour
• Visit Nesso Waterfall
• Cable car to Brunate for alpine views
• Explore Como Town’s cathedral and boutiques

Evening Tip: Toast to northern Italy with a glass of prosecco as lights shimmer across the lake.

Day 9 – Lake Como → Amalfi Coast (Travel Day)

Today is a travel day — but one that takes you from alpine serenity to Mediterranean beauty. Drive or take the train from Milan to Naples, then pick up another rental car for the Amalfi Coast.

As you descend toward the sea, the landscape transforms: jagged cliffs, pastel villages, and lemon groves mark your arrival in paradise.

Evening Tip: Settle in at Sorrento or Positano, have dinner overlooking the sea, and listen to the waves roll beneath a glowing sunset.

Day 10 – Amalfi Coast Drive: Positano, Amalfi & Atrani

Wake up to one of the most breathtaking drives in the world — the Amalfi Drive (SS163). Winding between cliffs and sea, each turn reveals a postcard view.

Start in Positano, where pastel houses cascade toward the beach. Continue to Amalfi Town to visit its cathedral, then stroll to Atrani, Italy’s smallest seaside village. Stop often, not because you must, but because you’ll want to.

Things to Do:

• Explore Positano’s boutiques and cafés
• Visit Amalfi Cathedral
• Walk to Atrani’s quiet beach
• Stop for photos at Furore Fjord

Evening Tip: Enjoy dinner at Le Sirenuse — one of the most romantic restaurants on the coast.

Day 11 – Ravello: Music, Gardens, and Views from Above

High above the Amalfi Coast lies Ravello, a serene escape known for its gardens, music, and sweeping views. The drive up is steep but rewarding.

Spend your morning wandering through Villa Rufolo and Villa Cimbrone, whose Terrace of Infinity offers views that seem to float above the sea. Visit local ceramic shops, enjoy espresso in the square, and savor the quiet — Ravello is a place that feels timeless.

Things to Do:

• Explore Villa Cimbrone & Villa Rufolo
• Attend a classical concert (summer only)
• Visit Minori or Scala nearby
• Try lemon pastries at Sal De Riso in Minori

Evening Tip: Stay overnight in Ravello for tranquility and a sky full of stars.

Day 12 – Capri Island: The Jewel of the Tyrrhenian Sea

Take a ferry from Amalfi or Sorrento to Capri, a glamorous island loved by artists and emperors alike. The island’s cliffs, grottos, and gardens are postcard-perfect.

Tour the Blue Grotto, take the chairlift to Monte Solaro, and wander the elegant streets of Anacapri. For hikers, the Pizzolungo Trail offers spectacular sea views leading to the Arco Naturale, a natural limestone arch.

Things to Do:

• Visit Blue Grotto & Anacapri
• Chairlift to Monte Solaro
• Hike the Pizzolungo Trail
• Shop or dine in Capri Town

Evening Tip: Watch the sun set over the Faraglioni rocks from Da Luigi ai Faraglioni — pure magic.

Day 13 – Sorrento & Pompeii: Ancient History Meets Coastal Charm

Spend your final full day exploring history and relaxation. Start with Pompeii, where ancient streets, villas, and frescoes were preserved under volcanic ash. Then drive up Mount Vesuvius for panoramic views of the Bay of Naples.

Return to Sorrento, a lively town of lemon trees and sea views. Stroll through the Marina Grande, shop for souvenirs, or relax with pizza and limoncello by the water.

Things to Do:

• Explore Pompeii ruins
• Hike Mount Vesuvius
• Visit Sorrento’s old town & Marina Grande
• Try fresh seafood pasta

Evening Tip: Celebrate your last coastal night with dinner at Grand Hotel Excelsior Vittoria.

Day 14 – Return to Rome: Farewell, Italia

After breakfast, begin your final drive back to Rome (about 4 hours). If time allows, stop in Civita di Bagnoregio, a fairytale village perched on a crumbling cliff — the perfect poetic ending to your journey.

As you return to Rome, grab one last espresso, soak up the sounds of Italian chatter, and reflect on the two weeks you’ve just lived — art, sea, food, and unforgettable memories.

Route Summary + Driving Distances

Route	Distance	Drive Time	Notes
Rome → Florence	170 mi / 275 km	~3 hrs	Scenic “Highway of the Sun” through Tuscany
Florence → Venice	160 mi / 260 km	~3 hrs	Flat, easy route (train recommended)
Venice → Lake Como	190 mi / 305 km	~3.5 hrs	Stop in Verona or Bergamo en route
Lake Como → Naples (flight/train)	—	1 hr flight / 5 hr train	Save time vs. 8+ hr drive
Naples → Amalfi Coast	40 mi / 65 km	~2 hrs	Stunning but narrow roads
Amalfi Coast Loop	25 mi / 40 km	~1.5 hrs	Allow extra time for photos
Sorrento → Pompeii → Rome	165 mi / 265 km	~4 hrs	Great final stretch with optional stops

Total Distance: ~1,500 miles (2,400 km)
Estimated Drive Time: ~25–28 hours total

Driving Tips for Italy

• ZTL Zones: Many cities restrict traffic in historic centers. Park outside and walk or use public transport.
• Autostrada (A1, A4): Fast, tolled highways — take a ticket upon entry and pay at exit.
• Fuel: Gasoline = Benzina, Diesel = Gasolio. Pay attention to labels.
• Parking: Blue lines = paid, white = free, yellow = reserved (avoid).
• Speed Limits: 130 km/h (highways), 90 (rural), 50 (urban).
• Coastal Roads: Drive slowly; locals may pass quickly. Pull over and let them.
• Car Rental Tip: Choose a compact vehicle for narrow streets and parking ease.
• Best Scenic Detours: Val d’Orcia (Tuscany), Verona, Nesso Waterfall (Como), and Civita di Bagnoregio.

Best Times to Go

• April – June: Ideal weather, blooming landscapes, fewer crowds.
• September – October: Warm seas, golden light, harvest festivals, and mild temperatures.
• July – August: Busy and hot, especially along the coast.
• November – March: Quieter and cheaper; best for city sightseeing.

Packing List

• Comfortable walking shoes
• Light layers and a jacket for cool evenings
• Swimsuit and sandals
• Sunglasses and hat
• Reusable water bottle
• Universal power adapter (Type C/F/L)
• Camera and portable charger
• Compact luggage for small cars
• Daypack for hikes and ferries

Where to Stay

Destination	Hotel Options
Rome	Check Hotels
Florence	Check Hotels
Venice	Check Hotels
Lake Como	Check Hotels
Positano	Check Hotels
Ravello	Check Hotels
Capri	Check Hotels
Sorrento	Check Hotels

Fun Facts

• Italy has 55 UNESCO World Heritage Sites, the most in the world.
• Venice is built on over 400 bridges and 118 islands.
• Ravello inspired composer Richard Wagner’s opera Parsifal.
• Lake Como’s shape resembles an inverted “Y.”
• The Amalfi Drive took over 150 years to complete.
• Italians consume about 60 pounds of pasta per person per year!

7 Things to Know Before Taking an Italy Road Trip

1. Know the Driving Rules – You’ll need an International Driving Permit along with your regular license. Speed limits and traffic cameras are strictly enforced throughout Italy.
2. Plan Your Route Ahead – Italy’s scenic roads—from the Amalfi Coast to Tuscany—are stunning but winding. Use GPS, but double-check directions since smaller roads can be confusing.
3. Avoid ZTL Zones – Many Italian towns have restricted driving areas (Zona a Traffico Limitato). Entering without a permit can lead to hefty fines, even for tourists.
4. Fuel Up Smartly – Gas stations close during midday breaks and on Sundays in smaller towns. Always top off your tank before heading into rural areas.
5. Parking Can Be Tricky – Look for blue lines (paid), white lines (free), and avoid yellow (reserved). In tourist areas, public garages are often the easiest option.
6. Bring Cash for Tolls and Small Stops – Highways (autostrade) charge tolls, and small restaurants or parking spots may not accept cards.
7. Stay Secure on Public Wi-Fi – You’ll likely use hotel, café, or roadside Wi-Fi to plan routes or book stays. Keep your data private with NordVPN — it protects your information, hides your location, and keeps you safe while exploring Italy online.

Final Thoughts

A 14-day Italy road trip is more than a vacation, it’s an immersion into a way of life. From the Renaissance glow of Florence to the cliffside calm of Ravello, every moment feels cinematic.

By taking your time, each region becomes a story of its own, a sip of wine in Chianti, a ferry crossing on Lake Como, a sunset on the Amalfi cliffs. This journey isn’t about checking off landmarks; it’s about feeling Italy, slowly, deeply, and joyfully. Drive slowly. Eat well. Wander freely. Because in Italy, the journey itself is the destination.

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