Southern Italy is a tapestry of ancient empires and contemporary pleasures—Greek temples and Baroque palazzi, sea-cliff roads and sun-warmed piazzas. In late September and early October, the crowds thin, the sea stays warm, and harvest festivals spill through village streets. This is the perfect shoulder-season window for a romantic road trip focused on food, coffee, shopping, and living like a local.

Over 14 days, you’ll base yourselves in three unforgettable places: Sorrento for the Amalfi Coast and Pompeii; Matera for cave-dwelling history and day trips into Puglia’s whitewashed towns; and Ortigia, the island heart of Siracusa, for golden-stone lanes, markets, and an easy springboard to Noto, Etna, and Taormina. Expect leisurely breakfasts, afternoon swims, and candlelit dinners with just the right amount of sightseeing and curated experiences.

Practical notes: Italian cities and historic centers enforce ZTL (limited-traffic) zones—park in signed lots at town edges. The Amalfi Coast’s SS163 is narrow and scenic; start early and consider parking once then exploring by local buses/boats. Ferrying your car from Calabria to Sicily is straightforward. Typical temps range from 70–80°F (21–27°C) early in the trip to pleasantly mild by mid-October. Culinary highlights include Campania’s lemons and mozzarella, Basilicata’s famed bread, and Sicily’s pistachio, citrus, tuna, and Etna wines.

Sorrento & The Amalfi Coast (Campania)

Sorrento makes a smart, romantic base: sunset terraces above the Bay of Naples, easy access to Positano/Amalfi/Ravello, Capri, and archaeological icons like Pompeii and Herculaneum. It’s lively without being overwhelming and offers excellent mid-range stays, trattorie, and cafés woven through citrus gardens and marquetry workshops.

Highlights include the cliff-side old town and Marina Grande, Ravello’s panoramic gardens, the Path of the Gods hike, and limoncello tastings. Late September often coincides with grape harvest celebrations inland; ceramic lovers should leave room in the trunk for a quick detour to Vietri sul Mare’s hand-painted wares.

Days 1–2: Sorrento settle-in, old town, and Naples pizza

• Stroll & espresso: Start at Piazza Tasso and Corso Italia. For a classic espresso or cappuccino, grab a table at Bar Fauno and watch the passeggiata.
• Sea air: Wander down to Marina Grande, a working cove. Lunch at Trattoria da Emilia for spaghetti alle vongole and views of bobbing boats.
• Naples afternoon (optional): Train or drive in for history and espresso culture. Try Gran Caffè Gambrinus for a Neapolitan caffè and Antica Pizzeria Da Michele or Gino Sorbillo for pizza (expect a wait; go early).

Days 3–4: Amalfi Coast day(s) – Positano, Amalfi & Ravello

• Early start drive: Follow the SS163 to Positano; park once and consider hopping coastal ferries or SITA buses to reduce driving stress.
• Positano: Browse linen boutiques and ceramic studios. Coffee at La Zagara with a lemon-glazed delizia al limone in its garden.
• Amalfi & paper history: Visit the Duomo and, time permitting, the Paper Museum. For pastries and a shot of espresso crema, Pasticceria Pansa is a must.
• Ravello: Late afternoon light in Villa Cimbrone’s Terrace of Infinity and Villa Rufolo gardens is as romantic as it gets. Dinner idea: Cumpà Cosimo, a pasta lover’s institution.

Day 5: Capri or Pompeii

• Capri day trip: From Sorrento’s Marina Piccola. Ride up to Anacapri, walk the Via Krupp, or boat around the Faraglioni. Split a seafood lunch at Da Gelsomina (sunset views if you stay late).
• Pompeii alternative: Beat the crowds by entering early; pair with Herculaneum for a more intimate ruin experience. Refuel with sfogliatella at a local pasticceria on the way back.

Where to stay (mid-range & romantic): Sorrento old town for walk-everywhere convenience; Marina Grande for fishermen’s-cove vibes; nearby Sant’Agnello for better parking values. Browse stays on VRBO or compare hotels on Hotels.com.

Good eats & coffee in Sorrento: Breakfast at Il Buco Bakery Corner for cornetti; mid-day panini and produce at Mercato di Sorrento; seafood sunset at Bagni Delfino on the water; garden dining under lemon trees at O’Parrucchiano La Favorita; gelato at Raki for inventive flavors.

Optional relevant tour if you begin in Rome:

Pompeii, Amalfi Coast and Positano Day Trip from Rome – useful if your trip starts in Rome and you want an overview before settling in Sorrento.

How to get here: Fly into Naples (NAP) or Rome (FCO). Check flights on Omio (flights to/from Europe) or Trip.com (global flights). From Rome to Naples, high-speed trains take ~1h10–1h20; browse schedules on Omio Trains. Naples to Sorrento is ~1h15 by car (plan €20–35/day for parking in Sorrento).

Drive to your next base (morning of Day 6): Sorrento to Matera is ~3h20 via A3/A2 and SS7 (allow €10–20 in tolls and fuel). Prefer public transit? Naples–Salerno–Ferrandina by train plus a short bus/taxi into the Sassi takes ~4.5–5 hours; check Omio Trains and Omio Buses for combinations.

Matera (Basilicata) + Day Trips into Puglia

With cave dwellings carved by hand and stone churches frescoed with Byzantine saints, Matera feels suspended in time. By dusk, the Sassi districts glow like a constellation—a natural stage for a romantic stroll and a slow dinner of orecchiette, local lamb, and Aglianico del Vulture.

Use Matera as a base to explore nearby Puglia: Alberobello’s trulli, Locorotondo’s white lanes, and Polignano a Mare’s sea grottoes and viewpoints. Late September often brings the Festa dei Santi Cosma e Damiano in Alberobello (processions, fireworks, street food), a local celebration worth planning around.

Days 6–7: Sassi deep dive, rock churches, and viewpoints

• Sasso Barisano & Sasso Caveoso: Walk the stone lanes, cave houses, and belvederes. Don’t miss Casa Noha for context and Santa Maria de Idris for a cliffside church.
• Pane di Matera & coffee: Try thick-crusted PDO bread from Panificio Perrone or Panificio Paoluccio. Espresso and pistachio cream cornetti at Caffè Schiuma.
• Romantic sunset: Watch golden hour from Belvedere Luigi Guerricchio or across the ravine on the Murgia plateau.
• Dinner: Trattoria del Caveoso (cave dining, hearty Basilicata dishes) or Baccanti (regional wines, refined plates in a stone vault).

Day 8: Alberobello, Locorotondo & Cisternino (Valle d’Itria)

• Alberobello morning: Explore the trulli districts (Rione Monti and Aia Piccola). If you’re here around Sept 25–27, catch the Santi Cosma e Damiano festivities.
• Locorotondo lunch: Whitewashed lanes and balcony geraniums. Order a carafe of the local bianco with bombette pugliesi (grilled meat rolls).
• Cisternino: Browse tiny butcher-grills and ceramics. Coffee stop at a corner bar before heading back to Matera.

Day 9: Polignano a Mare & Monopoli (Adriatic coast)

• Polignano morning: Walk to Lama Monachile viewpoint. Grab a seafood panino at Pescaria and a gelato at Martinucci Laboratory.
• Monopoli old port: Fortified walls, quiet churches, and mellow cafés. Aperitivo on Terrazza Santo Stefano if skies are clear.
• Back to Matera: Dinner of cavatelli and cruschi peppers at a cozy osteria.

Where to stay: Consider a cave-suite hotel for one or two nights and a modern apartment near the edge of the Sassi for easier parking. Browse options on VRBO or compare hotels on Hotels.com. Expect €15–25/day for parking near the Sassi.

Drive to your next base (morning of Day 10): Matera to Siracusa-Ortigia is ~6–7 hours by car. Route: A2 south to Villa San Giovanni, ferry (20–30 minutes; car + passengers ~€40–45 one way), then A18 to Siracusa (toll ~€3–5). If you prefer to skip the long drive, drop the car in Naples/Bari and fly to Catania; check Omio Flights. From Catania, pick up a new rental and it’s ~50 minutes to Ortigia.

For ferry lookups around Europe, see Omio Ferries; for alternative long-distance trains and buses, compare on Omio Trains and Omio Buses.

Siracusa – Ortigia (Sicily)

Ortigia is a tiny island with a grand soul: a honey-colored Duomo built into a Greek temple, fountains fed by freshwater springs, and a daily market perfumed with oregano, citrus, and tuna on ice. It’s intimate, walkable, and endlessly romantic—a perfect finale for your southern Italy itinerary.

Use it as a base for the Baroque jewel of Noto, nature at Vendicari, Etna’s lava slopes and wineries, and a Taormina capstone if you crave one last theater-with-a-view. Sundays in October often bring the food-centric Ottobrata Zafferanese in Zafferana Etnea (near Etna), a delicious way to meet Sicily’s autumn.

Days 10–11: Ortigia’s lanes, market lunches, and seafront sunsets

• Market morning: Browse stalls on Via De Benedictis; order a life-changing sandwich at Caseificio Borderi (arrive before the lunch rush).
• Duomo & Caravaggio: Admire the cathedral’s Greek columns and stop in Santa Lucia alla Badia for a Caravaggio masterpiece.
• Seawalls & aperitivo: Walk the Lungomare di Levante. Aperitivo at MOON (organic wines) or Enoteca Solaria.
• Dinner: Locanda Maniace (intimate Sicilian plates), A Putia delle Cose Buone (homey classics), or Don Camillo (refined, for a splurge night).
• Coffee & sweets: Morning espresso at Caffè Apollo near the Temple of Apollo or Gran Caffè del Duomo on the square; finish with pistachio gelato at Gelateria Gusto.

Day 12: Noto & Vendicari

• Noto morning: Baroque facades glowing like butter. Coffee and almond granita at Caffè Sicilia—a Sicilian institution.
• Vendicari Reserve: Swim and walk the dunes if weather cooperates; look for flamingos on the saltpans.
• Marzamemi evening (optional): Tiny fishing village with twilight magic; seafood dinner on the piazzetta.

Day 13: Etna wine day or Zafferana festival (Sundays in October)

• Etna adventure: Drive the north or south slopes; visit wineries like those around Trecastagni and Viagrande for Nerello Mascalese and Carricante tastings.
• Festival option: Ottobrata Zafferanese (Sundays) features pistachio sweets, porcini, and local cheeses—arrive by late morning to beat traffic.

Day 14: Taormina finale or Ortigia at leisure

• Taormina day trip: ~1h20 drive. Greek Theater views over the bay; stroll Corso Umberto, ride the cable car to Isola Bella for a swim if warm.
• Ortigia unwind: Sleep in, museum-hop, and enjoy a last seaside dinner with local white wines.

Where to stay: On Ortigia for romance and car-free nights; park just outside the ZTL (Talete car park is convenient, hourly with day caps). Explore options on VRBO or compare on Hotels.com.

Local Festivals & Seasonal Notes (Late Sept/Early Oct)

• Alberobello – Santi Cosma e Damiano: Typically late September with parades, music, and fireworks.
• San Vito Lo Capo – Cous Cous Fest: Often late September; if you add a western Sicily detour, this is a food-lover’s magnet.
• Zafferana Etnea – Ottobrata: Sundays in October, each themed (pistachio, mushrooms, honey) with pop-up stalls and music.

Travel Logistics & Options

Open-jaw flights: For smoother routing, arrive via Naples (NAP) and depart via Catania (CTA). Compare Europe flights on Omio or global options on Trip.com. If you need non-Europe long-haul searches, also see Kiwi.com.

Trains & buses: For legs you don’t wish to drive (e.g., Rome–Naples, Naples–Bari), browse Omio Trains and Omio Buses. Ferries within Europe are on Omio Ferries.

Driving tips: Photograph your car before pickup, know your ZTL maps, carry coins or card for parking machines, and factor €1.50–3.00/hour for town lots. The Villa San Giovanni–Messina ferry runs frequently; allow 60–90 minutes total including queuing.

Optional Rome Add-On (If Your Flights Route Via Rome)

If you tack a night in Rome onto the front or back of your trip, these well-run tours help you see the essentials efficiently—ideal if you prefer guided highlights before heading south.

Rome: Colosseum, Roman Forum, and Palatine Hill Guided Tour

Winner 2025 Rome Twilight Trastevere Food Tour by Eating Europe

Vatican Museums, Sistine Chapel & St Peter’s Basilica Guided Tour

Browse Rome stays on VRBO or compare on Hotels.com. Trains south depart frequently; check Omio Trains.

Summary: This 14-day southern Italy itinerary blends coastline drama, ancient stone cities, and island romance with food-first experiences and time to breathe. In the glow of early autumn, you’ll toast the harvest by the sea, wander caves and Baroque squares, and return with a trunkful of ceramics, olive oil, and memories made just for two.