Skip to content
Tailor-made luxury journeys, planned around you +1 888 931 0363
Southern Italy Explorer: Naples to Positano

Tailor-made journey · Italy

Southern Italy Explorer: Naples to Positano

Duration
8 days
From
$6,395 pp

Tailor-made, always

Every itinerary shaped around your dates, pace and preferences.

One dedicated expert

The same person from the first conversation until you return.

Decades of experience

Over 35 years shaping bespoke journeys for discerning travelers.

This eight-day journey explores the heart of Southern Italy, home to the nation’s finest food and most beautiful scenery. 

Request a quote

At a glance...

From the vibrant streets of Naples to the quiet beauty of Sorrento, Capri and the Amalfi Coast, it’s a route that offers you the very best of Southern Italy at a pace that allows you to relax and treasure each moment.

Along the way, you’ll visit ancient ruins, taste regional wines, sail between islands and experience daily life in some of Italy’s most captivating coastal towns. Private transfers, guided experiences and comfortable boutique stays ensure a smooth and unhurried journey throughout.

Plan Your Trip
Southern Italy Explorer: Naples to Positano

In detail

Naples

Day 1

Naples

Arrive in Campania, where your private driver will meet you for the short transfer to your hotel in Naples. Once settled, join a guided evening walk through the city’s historic centre. Explore local markets, sample traditional street food and take in the lively atmosphere that defines southern Italy’s largest city.

Naples to Sorrento

Day 2

Naples to Sorrento

This morning, travel by private car to Mount Vesuvius and take a guided walk to the crater for views across the Bay of Naples. Afterwards, enjoy a relaxed lunch and wine tasting at a vineyard on the mountain’s slopes with stunning panoramic views.

Continue to Pompeii for a private guided tour of the archaeological site, where well-preserved streets and frescoes reveal everyday life in Roman times. Travel onwards to Sorrento for your overnight stay.

Sorrento

Day 3

Sorrento

Spend the day in the hills above Sorrento for a hands-on cooking experience at a local villa. Learn the techniques behind traditional pizza and pasta using seasonal ingredients, then sit down to enjoy your meal with wines from the estate. The afternoon is free to explore Sorrento or simply relax and take in the coastal views – the choice is entirely yours.

Sorrento to Capri

Day 4

Sorrento to Capri

After breakfast, transfer to the harbour for a private boat journey to Capri. Cruise along the coastline before arriving on the island, where a local driver will take you to your hotel. The rest of the day is at leisure – stroll through Capri Town’s narrow lanes, visit local boutiques or relax on the terrace overlooking the sea.

Capri

Day 5

Capri

Join your guide for a morning walk along the Path of the Forts, one of Capri’s most scenic and iconic trails. Learn about the island’s history as you follow the route between sea views and ancient watchtowers. The afternoon is free to visit the Blue Grotto, enjoy coffee in the Piazzetta or simply spend time by the water.

Capri to Positano

Day 6

Capri to Positano

Take a private boat back to the mainland, then continue by car along the Amalfi Coast to Positano. The afternoon is yours to settle in and explore at your own pace. Walk through colourful streets lined with cafés and boutiques or relax on the beach as the sun sets over the bay.

The Amalfi Coast

Day 7

The Amalfi Coast

Spend the day exploring the region with your private guide. Visit Amalfi to see its striking cathedral before travelling to Ravello for its panoramic gardens and villa terraces. Stop along the coast for photographs and a relaxed lunch before returning to Positano in the evening.

Departure

Day 8

Departure

Your driver will collect you for the transfer to Naples Airport for your flight home. The morning offers time for a final coffee overlooking the sea before saying farewell to southern Italy.

Plan Your Trip

Add your Do Not Disturb moment

The Vatican, After Hours Experience the Vatican as few ever do — in the calm of evening, guided by those who know its secrets best. This exclusive after-hours visit reveals the artistry and emotion behind the world’s most famous collection, offering time to pause, reflect, and truly see. Trastevere Step into Trastevere — the Rome locals keep for themselves. Wander ivy-lined streets with a private historian, meet artisans still shaping the city by hand, and pause for an unhurried meal in a hidden courtyard. A Do Not Disturb experience revealing the soul of Rome through ease and access. Roman Dining in Style Experience Rome’s culinary artistry in complete ease. From private gardens to hidden terraces, Roman Dining in Style is a Do Not Disturb moment where food, setting, and connection come together in perfect harmony. Roman Gardens Step beyond Rome’s busy streets into its quietest spaces. From Trastevere’s hidden courtyards to the grand gardens of Tivoli, The Roman Garden Escape is a Do Not Disturb experience designed for stillness, beauty, and time shared with those who matter most. The Colosseum Step inside Rome’s greatest monument in rare quiet. The Colosseum, Unveiled is a Do Not Disturb experience that reveals the arena’s hidden layers — from its underground chambers to its silent grandeur — guided by those who know its stories best. The Roman Forum Step through the ruins that shaped the modern world. Walking Through Time: The Roman Forum Reimagined is a Do Not Disturb experience revealing where power, philosophy, and architecture first met — and how the story of civilization still echoes between these stones. The Pantheon Step into Rome’s most enduring masterpiece. The Pantheon is a Do Not Disturb experience revealing the harmony between light, structure, and spirit — an encounter with timeless design that continues to define the modern world. Caravaggio’s Rome Step into the light and shadow of Caravaggio’s Rome. From hidden chapels to private collections, Caravaggio’s Rome is a Do Not Disturb experience that reveals the artist’s genius as it was meant to be seen — intimately, quietly, and in place. Rome, Reimagined See Rome through a modern lens. Modern Rome: Art, Design & Aperitivo is a Do Not Disturb experience revealing the city’s evolving creative spirit — from hidden studios and private galleries to an aperitivo shared above the skyline. The Last Supper A private visit to Leonardo’s Last Supper offers a rare chance to see one of the Renaissance’s most important works in near silence. This moment reveals the mural’s true scale, its fragile beauty and the architectural harmony of Santa Maria delle Grazie, all without the rush of standard viewing slots. The Duomo A private tour of the Duomo di Milano reveals the cathedral’s immense architecture, centuries of craftsmanship and the quiet beauty of its terraces, all without the pace and crowds of standard visits. This is Milan’s most iconic landmark experienced with time, clarity and space to appreciate its details. Venice Gondola Ride Experience a private gondola ride in Venice through peaceful canals. Avoid the crowds with a romantic, tailor-made tour led by expert gondoliers.

Your journey doesn’t start with a booking. It starts with a conversation.

Tell us how you want to feel, we’ll take it from there.

Our reviews

Our team brings over 35 years of experience in luxury travel, shaping bespoke journeys for discerning clients worldwide.

See more reviews on Trustpilot
Our trip was truly magical and full of core memories that will last us a lifetime.
Michael • Bora Bora Honeymoon★★★★★
“We just returned from an incredible journey through Ireland, and we couldn’t have had a better experience”
Brad • Ireland Adventure★★★★★
“This was a flawless experience. They took all our thoughts and perfectly curated the most beautiful honeymoon.”
Kris • Sicily Honeymoon★★★★★

Your next steps

Planning your trip should feel effortless.

  1. We Listen

    You share what matters, whether it is a destination, a feeling, or a moment worth celebrating.

  2. We Curate

    Your dedicated expert shapes a thoughtful, private itinerary tailored entirely around you.

  3. You Travel

    Every detail handled. Every moment considered. Support before, during, and after your journey.

Begin your journey

Tell us about your journey

Tell us how you want your time away to feel. Your dedicated expert will be in touch to begin shaping it around you.

Or speak with us

+1 888 931 0363
Rich RyanDelwyn HughesJemima HanrottMaria GardnerSamantha McCormack

Your enquiry goes straight to one of our travel experts, who will reply to you personally.

Rich, Delwyn, Jemima and the team

    Budget per person

    By submitting you confirm you have read our Privacy Policy.