2 Week Dream Itinerary in Southern Italy

Tue Jan 30 2024

|Rileigh Tower

Where to Start Your Italy Road Trip? Italy is a country full of history, culture, art, food, and stunning scenery. From the rolling hills of Tuscany to the canals of Venice, Italy has something to offer every traveler

Post image

Where to Start Your Italy Road Trip?

Italy is a country full of history, culture, art, food, and stunning scenery. From the rolling hills of Tuscany to the canals of Venice, Italy has something to offer every traveler. If you are planning a road trip in Italy, one incredibly rewarding route is through Southern Italy and the island of Sicily. This allows you to see everything from ancient ruins to rugged coastal drives.

Frequently Asked Questions

Some common questions when planning a Southern Italy road trip include:

  • How much time do I need? Most itineraries are at least 2 weeks to fully experience the regions. You can cover the highlights in 10 days to 2 weeks if pressed for time.
  • What is the best time to visit Southern Italy? Late spring and early fall are ideal to avoid extreme heat and crowds. Summer is popular but very busy.
  • What is the best way to get around? Having a rental car allows the most flexibility to explore small hillside towns. Trains connect major cities. Ferries link the mainland to Sicily.
  • Where should I start my Italian road trip? Naples, Rome, and Bari are common starting points to kick off a Southern Italy road trip.

Related Searches

  • Amalfi Coast tours
  • Sicily tours
  • Italy itinerary 2 weeks
  • Italy road trip
  • Italy travel tips


Proper preparation goes a long way towards an enjoyable Italy road trip. Here are some tips before you hit the open road.

Travel Tips Before You “Andiamo!”

  • Get an international driver’s license. This will make renting a car and navigating Italian roads much smoother.
  • Plan your route. Decide if you want to see more of the coast or the interior regions. This will help maximize your time.
  • Learn some basic Italian phrases. Though many Italians in tourism centers speak English, knowing some Italian will help connect with locals.
  • Pack light. Space in rental cars is limited. Only bring essentials to remain flexible and comfortable driving.
  • Get travel insurance. Protect yourself with comprehensive medical and trip insurance. It’s worth the peace of mind.

Getting to Southern Italy

city skyline during golden hour

The major gateway cities to kick off your Southern Italy road trip include:

Naples – As the nearest major city to the stunning Amalfi Coast and islands of Capri and Ischia, Naples makes a convenient starting point.

Bari – Situated in the heel of Italy’s “boot,” Bari gives quick access to the remarkable scenery of Puglia.

Rome – Though a bit farther from Southern Italy’s most popular sites, you can see Rome’s iconic landmarks before heading south.

Many budget airlines offer cheap flights into these cities. Travelers starting elsewhere in Europe can take high-speed trains as well.

Tips for Traveling Around Southern Italy

  • Get a GPS navigator. It’s invaluable for navigating remote country roads. Download offline maps too.
  • Make accommodation reservations in advance during peak summer months.
  • Stop often! Part of the fun is leisurely enjoying little seaside towns.
  • Refuel frequently. Stations may be scarce in rural areas.

Southern Italy Road Trip Tips

  • Prepare for winding, narrow roads
  • Don’t rely on public transport outside major hubs
  • Avoid driving at night – roads are poorly lit
  • Always carry cash – smaller shops don’t accept cards

Detailed Itinerary for Week 1

During your first week, meander through Southern Italy’s most picturesque and fascinating regions.

Day 1-2: Puglia

white concrete building on brown grass field near body of water during daytime

This fairytale region has it all – charming hillside towns, ancient castles, delicious food, and miles of coastline.

Alberobello – Admire the unique trulli homes and overnight in one of these conical dwellings
Ostuni – Wander cobbled lanes in this whitewashed gem perched on a hill
Polignano a Mare – Enjoy fresh seafood and dramatic ocean vistas

Day 3-4: Campania

white and brown concrete building near mountain during daytime

Rolling pastoral landscapes meet enticing coastal scenery in this richly historic region.

Salerno – Base yourself in this vibrant city close to popular attractions
Amalfi Coast – Soak in postcard-perfect Positano, see the cathedral in Amalfi town, and drive the famed coastal road
Paestum – Marvel at some of Italy’s best preserved Greek ruins

Day 5-6: Sorrento & Capri

boat near island

The jet-set playgrounds of the rich and famous dazzle with their natural beauty and glamorous charm.

Sorrento – Stroll through chic piazzas surrounded by orange and lemon groves
Capri – Hop on a boat and explore the fabled Blue Grotto, emerald coves, and hilltop Anacapri
Ravello – Visit elaborately decorated villas overlooking azure waters

Detailed Itinerary for Week 2

The second week takes you to Sicily – the Mediterranean’s largest and most diverse island.

Day 7: Naples to Palermo Overnight Ferry

white boat on sea near mountain during daytime

Start your day in magnificent Naples. Spend your day exploring the rich history, vibrant street life, and mouth-watering cuisine. As afternoon folds into evening, depart for Palermo by an overnight ferry. Enjoy a serene sunset at sea as you float into the enchanting world of Sicily. Wake up in the morning to Palermo welcoming you with her open arms. The city’s charming chaos and cultural richness strike you as soon as you step foot off the ferry. Check into your hotel and plunge yourself headfirst into the Sicilian life. Dive into the Arabic-influenced lanes and treat your taste buds to the delectable local street food. Welcome to Palermo; she’s buzzing, intriguing, and ready to be explored.

Day 8-11: Palermo & Surroundings

a row of stone pillars next to a building

Use Palermo as your base to explore western Sicily’s top sights.

Monreale – Be awestruck by the magnificent 12th century cathedral and its dazzling golden mosaics. Don’t miss the cloister garden.
Marsala – Venture to this coastal town for wine tastings in Sicily’s most famous wine region. Segesta – Journey an hour west of Palermo to tour this remarkably intact 5th century BC Greek temple and amphitheater. 

Erice – Explore this spectacular hilltop medieval town with Norman castles and sweeping coastal views.

Day 12-14: Over to Eastern Sicily

aerial view of city near body of water during daytime

Traverse the island taking in the iconic sights around Mount Etna and the cultural gems of Taormina and Siracusa.

Taormina – Soak up the sophisticated resort-town vibe with its chic cafes and boutiques. Catch an evening show at the ancient Greek amphitheater.

Siracusa – Step back in time wandering this 2,700-year-old city’s labyrinth old town. See Greek and Roman monuments before enjoying fresh seafood by the waterfront.

Exploring Sicily

Beyond the well-known cities and tourist routes, Sicily offers intrepid travelers cultural treasures and offbeat adventures.

Street Food Tour in Palermo

Leave the guidebook behind and embark on an immersive walking tour to discover the island through its vibrant street food scene. Graze your way through buzzing markets trying local specialties like panelle chickpea fritters, arancini fried rice balls, and sfincione Sicilian pizza. This is the best way to experience Palermo like a local!

Monreale Cathedral

This 12th century Norman-Arab-Byzantine cathedral located just outside Palermo exemplifies Sicily’s diverse cultural influences. Mouths gape open entering the golden nave decorated with over 6,500 square meters of precious Byzantine mosaics – acclaimed among the world’s finest. Don’t miss the peaceful cloister garden offering nice views overlooking the Conca d’Oro valley.

Segesta Archeological Park

Take a trip back to ancient Greece while exploring this large 5th century BC temple. Set on the edge of a canyon amid hilly farmland, Segesta’s remarkably intact Doric-style temple has 36 columns still standing tall. Hike up to the ancient theater for a scenic picnic spot overlooking the temple. Wander through wildflowers and get lost among the mysteries of this once powerful Sicilian outpost.

Additional Tour Spots in Southern Italy

Beyond the greatest hits along the Amalfi Coast and Sicily, Southern Italy has many small towns and sites worth adding to your itinerary.

Guided Tour of Trapani

Most visitors neglect Sicily’s western tip, but Trapani has compelling historic sights paired with a laidback local vibe. Its pedestrian historic center and coastline resemble a mini Marseille in Italy. Foodies will love grazing at tiny shops selling the sea salt and windmill-ground flour the area is known for. Nature lovers can take boat trips to the nearby Egadi Islands through crystal blue waters to spot dolphins.

Guided Tour of Marsala & Its Saltpans

Famous for its sweet dessert wines, the small coastal town of Marsala has another claim to fame – Garibaldi first set foot in Sicily here during the Italian Unification. Learn about this history while tasting marsala wine at old cantinas. Visit the Stagnone Lagoon to see windmills pumping sea water into basins to harvest prized sea salt for centuries.

Guided Tour of Selinunte Archaeological Park

One of Sicily’s most impressive ancient Greek ruins lies isolated on its southwestern coast. Selinunte was once the mightiest Greek colony of the Mediterranean before being ransacked by the Carthaginians. Today it remains one of the largest archaeological sites in Europe. Visitors can walk around the ruins of seven temples strewn amid olive and carob groves next to the sea.

Further Explorations

For travelers with more time or specific interests, Southern Italy has countless opportunities to dive deeper into its natural landscapes and cultural gems.

Excursion on Mount Etna By Cable Car & Jeep

Dominating eastern Sicily, Mount Etna is Europe’s tallest and most active volcano. Take a scenic cable car ride up its flanks for thrilling views inside the summit craters. Or for more adventure, bump along in a 4×4 jeep over ancient lava flows towards crater edges for a peek into the volcano’s power. Local expert guides share stories bringing context to safely experience this marvel of nature.

Historical Museum of the Landing in Sicily & Catania War Cemetery

To learn about the 1943 Allied landing on Sicily’s eastern shores, this museum 50 minutes north of Catania uses films, photographs, and wartime relics to vividly chronicle the events. Just up the road lies the Catania War Cemetery where over 5,000 WWII Allied soldiers are buried. Standing at the memorial amid rows of headstones – including many Canadians and Australians so far from home – makes for a sobering history lesson.

Guided Tour of Taormina & Its Ancient Theatre

Though often crowded, Taormina’s scenic beauty and ancient sites should not be missed. Find an experienced local guide to provide context bringing the destination to life. Learn about Taormina’s Greek, Roman, and medieval histories while hearing insights into contemporary culture. Ensure seeing the wonderfully preserved Greco-Roman amphitheater hosting summer concerts against a backdrop of Mt Etna and the sea.

If You Have More Time

Two weeks provides sufficient time to explore Southern Italy’s most famous sights at a comfortable pace. But with more time come more opportunities off the beaten track!

How to Extend Your Southern Italy Road Trip

An extra week or more allows you to immerse deeper into Southern Italy’s culture, secluded corners, and outer islands. Here’s how to make the most of added time:

Slow down – Stay longer in places you love instead of cramming in more stops
Sail the islands – Hop aboard a yacht or ferry for Sicily’s remote Egadi and Aeolian Islands
Get active – Kayak along the Amalfi Coast or hike Mount Etna and the Apennine Mountains
Go local – Rent an apartment through homestay networks, shop at markets, take cooking classes

Other Example Italy Tour Itineraries

To help you extend your Southern Italy trip or design a custom route, here are some other popular Italy itineraries:

1 Month – Rome > Amalfi Coast > Sicily > Venice & Northern Lakes > Tuscany & Cinque Terre

6 Weeks – Venice > Cinque Terre > Tuscany > Umbria > Rome > Amalfi Coast & Southern Italy

2 Weeks – Rome & Highlights > Florence & Tuscany > Venice

If You Have Less Time

If under 2 weeks, it’s best to focus your journey instead of cramming too much ground. Here’s how to craft an exceptional 10 to 14 day Southern Italy experience.

If You Have LESS Time in Italy

Narrow your focus to a couple regions done at a relaxed pace instead of dashing through packed days:

Amalfi Coast & Capri – Base yourself here with day trips Sicily – Focus only on Palermo, Taormina, Siracusa Puglia – Explore charming hill towns at leisure

Or take the train between must-see spots:

Rome > Amalfi Coast > Sicily

Travel Guides and Resources

Taking advantage of local expertise goes a long way to enriching your experience in a new destination! Here are reputable companies providing helpful trip-planning services:

Qualified Guides. Certified Excellence.

Context Travel’s top notch PhD and expert guides offer small group and private walking seminars bringing depth and insider access. Food tours available too!

Italy With Pleasure crafts customized itineraries, escorted tours, and exclusive experiences focused on Southern Italy tailor-made to your travel style.

Plan a Trip to Southern Italy

These reputable online travel agents can help with trip planning:

Go Ahead Tours— Guided tours in Italy Auto Europe— Car rentals made easy GetYourGuide— Handpicked activities & day tours

Or Start Planning Your Perfect Italy Tour Itinerary Today

For help crafting your dream trip itinerary, get in touch with us at Travel Mellow

Conclusion: 2 Weeks in Italy from Naples to Sicily

Over 2 weeks you can marvel at many of Southern Italy’s natural and cultural highlights. Begin along the steep coasts of the Sorrentine Peninsula before traversing the Tyrrhenian Sea to Sicily. Along the way soak up the picturesque charm of pastel-hued fishing villages, sample delectable cuisine, explore ancient sites, and soak up sunny Mediterranean vibes. From the electric pulse of Naples to Palermo’s exotic grit, culture and history come alive.

Beyond the well-trodden tourist routes, take time to lingering over aperitivo happy hour or meandering through open-air markets. Or set off from lesser-visited Matera, Puglia or Calabria to appreciate the rhythms of small town Italian life unchanged for generations.

Whether you seek famous bucket-list attractions or aim to simply eat, drink, and relax in style, Southern Italy guarantees memories to last a lifetime!

Thank You for Your Interest!

I hope this detailed article helps you craft an exceptional trip through Southern Italy and Sicily. Please don’t hesitate to reach out with any other questions as you firm up your travel plans.

It’s my passion to provide insider expertise so visitors can experience the authentic spirit of this special region. Have an amazing journey!

profile icon of Rileigh Tower

About the Author

Rileigh Tower

Join the Travel Mellow Travel Club!

Sign up for exclusive deals and insider information on Italian Travel and beyond! No spam, ever.