Tailor-made Holiday · Italy
Southern Italy and Amalfi Coast Explorer
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Every trip built from scratch around your dates, pace and preferences.
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At a glance
Southern Italy is at its best when you combine the bustling streets of Naples with historic Pompeii, the slower pace of Sorrento, and a few days on the Amalfi Coast and Capri.
Your journey begins in Naples, where private transfers and guided touring give you an introduction to one of Italy’s most characterful cities.
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There is exceptional food, layers of history and a sense of life happening all around you. From there, travel south towards Mount Vesuvius and Pompeii, with time for a vineyard lunch before continuing to Sorrento.
In Sorrento, the pace slows. Spend time at a private villa learning to make pizza and pasta, then continue by private boat to Capri, where sea views, cliffside walks and evenings in Capri Town give you time to enjoy the island beyond the usual day-trip rush.
The final part of the journey brings you to Positano and the Amalfi Coast, with private touring through Amalfi and Ravello, time on the water and enough flexibility to enjoy the coast rather than simply move through it.
This is an eight-day itinerary, but everything can be tailored around you. We can upgrade hotels, slow the pace, add extra nights on Capri or the Amalfi Coast, or build in more private dining, boat days and cultural experiences.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Day 1: Naples
Arrive at Naples Airport, where your private driver will meet you and transfer you to your hotel in the city.
Later, join a private guide for an introduction to Naples on foot. Explore the historic center, learn how the city’s Greek, Roman and Bourbon past still shapes it today, and stop for some of the street food Naples is famous for (pizza was invented here!).
It is a lively first evening and a good way to understand the city before heading further south.
Day 2: Naples to Sorrento via Pompeii
Leave Naples by private car and travel south to Pompeii, where a private guide will bring the ancient Roman city to life.
Walk through its preserved streets, villas, baths and public buildings, with time to see the frescoes and mosaics that survived the eruption of AD 79. Rather than rushing through, you’ll have enough time to properly explore the site and understand how people lived here almost 2,000 years ago.
Afterwards, stop for lunch before continuing along the Bay of Naples to Sorrento, where you’ll check into your hotel and have the evening at leisure.
Day 3: Sorrento
Spend the day at a villa outside Sorrento for a hands-on cooking experience using local ingredients.
Learn to make classic pizza and pasta, sit down to eat what you have prepared, and enjoy wine from the surrounding area.
The rest of the day is left open, giving you time to enjoy the hotel, explore Sorrento or simply slow the pace before heading to Capri.
Day 4: Sorrento to Capri
Travel to the marina and board a private boat for the journey across to Capri.
Approaching the island from the water is part of the experience, with limestone cliffs rising sharply from the sea before you arrive.
A private transfer will take you to your hotel, then the afternoon is yours. Walk through Capri Town, browse the boutiques, stop for a drink in the Piazzetta or settle in at the hotel and enjoy the views.
Day 5: Capri
Spend the morning exploring another side of Capri on foot.
The Path of the Forts follows the island’s western coastline, linking historic defensive sites with some of Capri’s best sea views.
The afternoon is deliberately free. Return to Capri Town, find a quiet lunch spot, spend time by the pool or simply enjoy the island at a slower pace once the day-trippers begin to leave.
Day 6: Capri to Positano
After a relaxed morning, return to the mainland by private boat and continue by private transfer to Positano.
Built almost vertically into the cliffs, Positano is one of the Amalfi Coast’s most recognizable towns, but staying overnight lets you experience it beyond the busiest hours of the day.
Settle into your hotel and spend the afternoon by the pool, exploring the lanes around town or heading down towards the beach for an early evening drink.
Day 7: The Amalfi Coast
Spend the day exploring the coast with a private guide and driver.
Begin in Amalfi, with time to see the cathedral and wander through the historic center before continuing uphill to Ravello.
Here, visit Villa Rufolo or Villa Cimbrone, both known for their gardens and extraordinary views over the coastline.
Return to Positano later in the afternoon, with the evening free for dinner at your hotel or in town.
Day 8: Departure
Your private driver will collect you from the hotel for the journey back to Naples Airport.
If you have more time, this itinerary can easily be extended with additional nights on Capri, along the Amalfi Coast or elsewhere in southern Italy.
Our Experts
Italy is one of the best places in Europe to experience culture, food and beautiful scenery. With so much character and colour, the Amalfi Coast is a personal favourite of mine.
I never get tired of planning luxury vacations in Italy. There are so many magical cities and experiences to be enjoyed. Beaches, mountains and rolling countryside, there really is something for everyone.
Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalised experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalised itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travellers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of travelling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first enquiry to homecoming. No call centre, and nothing is charged until you decide to book.