Tailor-made Southern Italy trip

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Fascinating Southern Italy trip invites curious travelers to taste wood-fired pizza in Naples, wander lemon-scented lanes in Sorrento, and hop on a private boat to Capri's azure coves.

Designed for travelers craving authentic, tailor-made travel, this experience blends local guides, hidden ateliers, and handpicked dining into a personalised journey.

Tell us your pace and passions, and we will craft a trip to Italy that turns moments into lasting memories. Start planning today and discover Southern Italy on your terms.

Southern Italy trip highlights

  • Neapolitan culinary journey: Taste true Naples with a tailor-made food tour of pizzerias and markets.
  • Scenic Sorrento and Amalfi drive: Drive Sorrento's cliffs and Amalfi curves in a private car.
  • Capri Island discovery: Explore Capri's grottos, hidden coves, and chic boutiques with a local guide.
  • Authentic local immersion: Stay in charming seafront guesthouses and meet artisans.
  • Personalized luxury and flexibility: Flexible, personalized service from planning to departure.
DayMorningAfternoonEvening
Day 1Arrive in Naples; private transfer to hotel and check-in.Free time to explore narrow streets or relax with bay views.Sample Neapolitan pizza or unwind at a local café.
Day 2Tailored Naples walking tour with a local guide: Piazza Plebiscito, Royal Palace, and Spaccanapoli.Street food tasting at Pignasecca market and visit to a traditional presepe artisan.Explore the Duomo and learn about Saint Gennaro.
Day 3Guided tour of Pompeii: thermal baths, frescoes, and the Basilica.Drive up Mount Vesuvius for lunch or wine tasting, then hike to the crater rim.Return to Naples for a relaxed evening.
Day 4Private transfer to Sorrento; two-hour walking tour with sea views and local insight.Optional food tasting: limoncello and regional specialties.Transfer to Positano; check in and explore the cliffside village.
Day 5Free morning in Positano: beach time, boutique shopping, or exploring the marina.Tailor-made options: boat trip, beach club access, or local cooking class.Dine on fresh seafood or enjoy a sunset drink.
Day 6Private boat tour along the Amalfi Coast with swimming stops in hidden bays.Explore Amalfi town or visit the Emerald Grotto (optional, paid locally).Return to Positano for dinner or a walk through town.
Day 7Transfer to Positano pier; hydrofoil to Capri and hotel check-in.Free time to explore the piazzetta, coastal paths, or relax by the pool.Discover Capri’s dining scene or enjoy a quiet evening.
Day 8Free day on Capri: boutique shopping, lemon groves, or hidden beaches.Private sunset cruise with prosecco, passing the Faraglioni.Toast to the trip as the sun sets over the sea.
Day 9Guided morning walk in Anacapri and Capri town; optional Augustus Gardens or Mt. Solaro chairlift.Afternoon free to enjoy the island.Final dinner in Capri or relaxed evening stroll.
Day 10Private transfer from hotel and hydrofoil to Naples.Optional final coffee stop or photos en route to the airport.Departure from Italy. Safe travels home.

Places you'll visit

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Naples
NaplesCampania
Day01

Day 1: Arrival in Naples

Upon arrival in Naples, your private driver will meet you at the airport and transfer you to your hotel for check-in.

Spend the afternoon at leisure exploring narrow streets or relaxing with views of the bay. This Southern Italy trip blends tailored experiences, tastings of Neapolitan pizza, guided walks around Mt Vesuvius, and optional boat trips to Sorrento and Capri. Our local team crafts every detail for an authentic Italian itinerary.

Naples
Day02

Day 2: Naples walking tour and street food

Join a local Neapolitan guide on a tailored walking tour to uncover Piazza Plebiscito and the Royal Palace. Stroll the seafront with views of the bay and Mt. Vesuvius, and wander Spaccanapoli through the historic centre.

Taste authentic street food at Pignasecca market, visit a craftsman to see traditional handmade presepe figures, and explore the Duomo to hear the story of Saint Gennaro.

Margherita Pizza Naples
Day03

Day 3: Pompeii and Vesuvius

Explore ancient Pompeii. Stroll through the ruins to see the thermal baths, the Lupanare frescos, the Macellum, and the Basilica.

Then drive up Mount Vesuvius and pause at a panoramic restaurant for pizza or a local wine tasting. Your driver takes you to 1000 m, then you walk to the crater rim with a park guide, enjoying views of Mount Somma, the Vesuvius cone, and the Valley of the Giant.

Pompeii
Day04

Day 4: Arrival in Positano and Sorrento

Your private driver collects you at the hotel for a tailored, two-hour private walking tour of Sorrento. Discover clifftop views across the Gulf of Naples to Mount Vesuvius and the islands of Procida, Ischia, and Capri.

Optional local food tasting available to sample limoncello and regional specialties. After the tour, your driver transfers you to Positano for hotel check-in and leisure time to explore the colorful cliffside village.

Positano
Day05

Day 5: Free day in Positano

Positano sits vertically on the cliff face above the Amalfi Coast, a picture-perfect town of steep streets, boutique shops, and elegant restaurants. Enjoy a day at Positano Marina, lounging on the beach, swimming in crystal clear waters, and sampling fresh seafood.

Tailor-made options include private boat trips, beach club access, and a cooking experience with local chefs for an authentic Southern Italy itinerary.

Sorrento
Annalisa

Tips from Annalisa

Italy Travel Expert

quotes

Want to escape the crowds in Positano? Walk ten minutes from the main beach to Fornillo. It’s quieter, more relaxed, and still has sunbeds, beach bars, and the same jaw-dropping views. Locals prefer it for a reason.

Day06

Day 6: Amalfi Coast boat tour

Sail the stunning Amalfi Coast on a private boat tour, stopping in hidden bays for swimming and exploring grottoes and caves. Pass Praiano, the Fiordo di Furore, Conca dei Marini with the Emerald Grotto, and the historic maritime town of Amalfi.

Choose an optional Emerald Grotto visit paid locally, or take 2 to 3 hours of free time for lunch and wandering in Amalfi, then return to Positano.

Almafi
Day07

Day 7: Arrival in Capri

Walk down to Positano pier and catch the hydrofoil to Capri. On arrival, transfer to your hotel, check in, and enjoy a free afternoon to explore the piazzetta, relax by the pool, or stroll coastal paths.

Capri is famed for glamorous boutiques, ancient Roman villas from Emperor Tiberius, dramatic sea views, and intimate restaurants.

Capri
Day08

Day 8: Capri at leisure and sunset cruise

Enjoy a free day on Capri to relax and explore hidden coves, boutique shops, and fragrant lemon groves.

In the afternoon, enjoy an exclusive private sunset boat tour, glide past the Faraglioni, sip prosecco, and toast as sky and sea glow.

Capri
Day09

Day 9: Guided morning walk in Anacapri and Capri

Your private guide is at your disposal for the morning. Enjoy a short, tailored walk through Anacapri and Capri town centres, then choose a visit to the fragrant Augustus Gardens or ride the chairlift up to Mt. Solaro for panoramic views. The tour concludes around lunchtime, leaving the afternoon free to savor island life.

Capri
Day10

Day 10: Departure from Naples

Wrap up your trip with a private transfer from your hotel, hydrofoil tickets, and a ride from Naples pier to Capodichino Airport, all sorted for your afternoon flight.

Soak up the final views of Capri and Sorrento as you go. Think back on the food, the history, and those salty coastal moments. You’ve traveled Italy your way: authentic, personal, unforgettable. Safe journey home.

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