A Romantic 5-Day Naples Itinerary: History, Street Food, Capri Blue Grotto, and Pompeii

Fall for Naples and the Bay of Naples with five days of archaeology, cliffside views, and late-night street food. This romantic, mid-budget plan blends museums, hiking Vesuvius, Capri’s Blue Grotto, and living like a local.

Naples is ancient, rebellious, and irresistibly alive. Founded by the Greeks and later embraced by Rome, the city cradles world-class treasures like the National Archaeological Museum, baroque masterpieces, and the hauntingly preserved cities buried by Vesuvius. Its layers unfold in tight lanes perfumed by pizza dough, espresso, and sea breeze.

Romance here is different—sunset over Castel dell’Ovo, boat wakes flickering along the Lungomare, and a ferry skimming to Capri. Days stretch from museums to cliffside hikes, and nights hum with wine bars, jazz clubs, and late-evening pastas.

Practical notes: book timed tickets for popular sights (Veiled Christ/Cappella Sansevero), and wear comfy shoes for cobblestones. Keep an eye on your belongings in crowds. Eat the city: sfogliatella for breakfast, frittatina and cuoppo for lunch, and a margherita DOP with blistered cornicione for dinner.

Naples

Naples (Napoli) is Campania’s volcanic heart—art, archaeology, and appetites all dialed up. Top highlights include the National Archaeological Museum, Castel Sant’Elmo’s sweeping views, the colorful Spanish Quarter murals, and the Royal Palace by Piazza del Plebiscito.

  • Don’t-miss sights: MANN (Archaeological Museum), Cappella Sansevero (Veiled Christ), Santa Chiara’s maiolica cloister, Naples Underground, Castel dell’Ovo, Certosa di San Martino.
  • Romantic moments: Sunset along Via Partenope, Capri boat ride, Posillipo overlooks, a two-seat table in Chiaia with seafood and Falanghina.
  • Where to eat (local favorites): Pizzeria 50 Kalò (margherita DOP, long-fermented dough), Da Attilio (star-shaped “carnevale” pizza), Tandem (slow-cooked ragù), Osteria Il Gobbetto (homey Campanian plates), ‘A Figlia d’ ’o Marenaro (seafood, peppered mussels), Poppella (fiocchi di neve), Gran Caffè Gambrinus (historic espresso), Bar Mexico (the “crema” shot).

Where to stay (mid-budget and romantic picks):

Getting in and around:

  • Flights (Europe): Compare fares to NAP on Omio Flights. Many EU hubs offer nonstops; typical fares €40–€150 one way.
  • Flights (long-haul): Search multi-airline deals via Trip.com or Kiwi.com.
  • Trains (within Europe/Italy): Rome → Naples in ~1h10; Florence → Naples ~2h50. Check times and prices (€20–€70) on Omio Trains.
  • Airport transfer: Alibus shuttle to city ~15–25 minutes (~€5–€6). Taxis are ~€20–€25 to central areas (fixed-rate zones).
  • Ferries: Fast hydrofoils to Capri in ~45–50 minutes (€22–€28 each way). Compare on Omio Ferries.

Day 1: Historic Heart & Hands-On Pizza Night

Afternoon (arrival): Check in, then sip a first espresso at Gran Caffè Gambrinus by Piazza del Plebiscito—velvety and potent. Stroll the seafront to Castel dell’Ovo for a horizon of sails, then duck into the Historic Center along Spaccanapoli to read Naples in stone: Gesù Nuovo’s diamond façade and Santa Chiara’s serene maiolica cloister.

Evening: Learn and dine with an intimate pizza class—perfect for couples and a mid-budget splurge you’ll remember.

Authentic Pizza Making Class in Naples with Appetizers and Drink

Authentic Pizza Making Class in Naples with Appetizers and Drink on Viator

Prefer to just feast? Try Pizzeria 50 Kalò (light, airy crusts near the water) or Da Attilio (classic pies in the Quartieri Spagnoli). Finish with gelato at Casa Infante and a romantic stroll along Via Partenope’s lights.

Day 2: Museums, Underground Naples, and a Street Food Safari

Morning: Fuel up with a sfogliatella (riccia or frolla) at Scaturchio, then head to the National Archaeological Museum (MANN) for mosaics and frescoes rescued from Pompeii and Herculaneum. A quick espresso “al volo” at Bar Mexico by Piazza Dante keeps you on pace.

Lunch: Tandem serves slow-simmered ragù spooned onto pasta or tucked into bread—rich, comforting, very Napoletano. Street-food fans can sample Di Matteo’s frittatina di pasta and a paper cone of fried seafood (cuoppo).

Afternoon: Reserve the Cappella Sansevero to marvel at the Veiled Christ’s marble “fabric.” Then explore San Gregorio Armeno’s artisans crafting nativity figurines, and descend with a Naples Underground tour to Greek-Roman cisterns beneath the bustle.

Evening: Join a local for the tastiest orientation through the centro storico.

Authentic Naples Street Food Tour With Local Expert Guide

Authentic Naples Street Food Tour With Local Expert Guide on Viator

Nightcap options: L’Antiquario (speakeasy finesse), Enoteca Belledonne (cozy wine bar), or Bourbon Street for live jazz. Keep it local with a glass of Gragnano or Falanghina.

Day 3: Full-Day Pompeii Ruins and Mount Vesuvius Crater Walk

Step through time at Pompeii, then climb the sleeping volcano that sealed its fate. This small-group, all-inclusive day balances history with a short, rewarding hike and a Neapolitan lunch—great for your “sightseeing + hiking” wishlist.

Naples: Pompeii & Mt Vesuvius All-Inclusive Small Group w/ Lunch

Naples: Pompeii & Mt Vesuvius All-Inclusive Small Group w/ Lunch on Viator

What to expect: skip-the-line entry, guided ruins tour, bus to the park, a 20–30 minute walk up cinder paths to the crater rim, and sweeping Bay of Naples views. Wear sturdy shoes; bring water, sunhat, and a light layer for the breeze up top.

Optional evening back in Naples: Seafood dinner near Santa Lucia—try ‘A Figlia d’ ’o Marenaro for mussels and spaghetti alle vongole, or Osteria Il Gobbetto for a rustic spread. A limoncello toast by the harbor wraps the day.

Day 4: Capri Day Trip and the Blue Grotto

Chase alpenglow on the water and Capri’s luminous caves—one of the Mediterranean’s most romantic escapes. This guided day smooths the logistics: ferry, island transport, viewpoints, and that iconic boat glide into the Grotta Azzurra (sea conditions permitting).

Day Trip to Capri and Blue Grotto From Naples & Sorrento

Day Trip to Capri and Blue Grotto From Naples & Sorrento on Viator

Tips: if seas are rough, guides pivot to a coastal boat tour. Consider the chairlift from Anacapri to Monte Solaro for dreamy panoramas. Snack ideas: warm waffle cones at Buonocore and lemon granita along Capri town’s lanes.

Evening back in Naples: Dine in Chiaia—Umberto for Neapolitan classics, Trattoria da Ettore for seafood near the Castel dell’Ovo area, or La Scialuppa on Borgo Marinari for a waterside table. A moonlit walk along the Lungomare seals the romance.

Day 5: Markets, Hilltop Views, and Farewell

Morning: Start at Sfogliatella Mary (inside Galleria Umberto I) for a last sweet bite, then browse Pignasecca Market for cheeses, anchovies, and peperoncini to take home. Ride the funicular to Vomero for sweeping views from Castel Sant’Elmo and the art-filled Certosa di San Martino—terraces made for couple photos.

Lunch & departure: Quick bite ideas: a cuzzetiello (stuffed bread loaf) from O’ Cuzzetiello or a final margherita at Da Attilio. Collect your bags and head to the airport (Alibus or taxi) or Napoli Centrale for trains via Omio Trains. If you’re flying within Europe, compare fares on Omio Flights; for long-haul, check Trip.com or Kiwi.com.

Optional Swap: Amalfi Coast Panorama Day

If Capri isn’t your style, trade Day 4 for a scenic small-group drive hugging the cliffs, with photo stops and free time in Positano and Amalfi—intensely romantic vistas and lemon-scented lanes.

From Naples: Sorrento, Positano & Amalfi Coast – Small Group Tour

From Naples: Sorrento, Positano & Amalfi Coast – Small Group Tour on Viator

Expect a full day (with narrow, winding roads) and dozens of postcard angles. Budget around mid-level costs for a sit-down seaside lunch; or grab a panino and lemon sorbetto for more time on the beaches.

Cost-savvy tips for a 50/100 budget:

  • Mix trattorie and street food with one or two view-heavy dinners.
  • Buy museum combo tickets; book big sights in advance to avoid pricier last-minute slots.
  • Use the funiculars/metro and walk; taxis only at night or with luggage.

In five days, Naples becomes a love story—espresso-dashed mornings, history underfoot, and evenings that drift long past dinner. With Capri’s blues and Vesuvius’ black ash in the frame, you’ve tasted Campania’s soul and left room to return.

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