Tailor-made Vacation · Italy
Art & Cooking in Milan, Sorrento, Pompeii & Rome
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
Italy has long been celebrated as a mecca for lovers of art, history, and food. In this exclusive journey, you'll traverse the enchanting cities of Milan, Sorrento, Pompeii, and Rome, where art, culinary craftsmanship, and luxury living create an extraordinary tapestry of experiences.
Your Italian adventure begins in Milan, Northern Italy's gem. With a gay-friendly guide, explore iconic landmarks like Via Montenapoleone, the Milan Cathedral, and Galleria Vittorio Emanuele II. Immerse yourself in Italian cuisine through hands-on cooking classes, culminating in a delightful dinner. And for fashion enthusiasts, Milan's world-renowned boutiques await your exploration.
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Bid farewell to Milan and head to Sorrento. From here, you can explore the Amalfi Coast's dramatic cliffs, secluded beaches, and picturesque villages by private car. As a UNESCO World Heritage site, the Amalfi Coast offers a glimpse into a Mediterranean landscape unlike any other, boasting lemon groves, bountiful vineyards, and grand villas.
Explore Pompeii, frozen in time by Mount Vesuvius in AD 79. A guided tour unveils vivid remnants of a lost civilization. Afterward, try Naples' famed street foods like "panzerotti," "zeppole," and "cuoppo di pesce fritto." Explore Plebiscito Square, Umberto I Gallery, and Maschio Angioino.
Bid Naples farewell and board a high-speed train to Rome. Explore Ancient Rome with a guided tour featuring the Colosseum and Imperial Fora, and indulge in another cooking class.
Experience a fusion of luxury, art, and gastronomy on this unforgettable journey through Italy.
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 to 3: Milan
Upon arrival into Milan (airport or railway station), we will meet you and you’ll take a private drive to your hotel.
During your time in this beautiful city, you’ll take a walking tour with a gay-friendly guide in Milan. You’ll visit Via Montenapoleone, the Milan Cathedral, the Galleria Vittorio Emanuele II and the most important historical and artistic attractions.
After the tour, take an aperitif at Blanco, one of the most known gay bars in town during happy hour and, in the evening, explore the gay nightlife of Milan.
Whilst in Milan you’ll also try your first Italian cooking class. You’ll learn how to make pasta and risotto, followed by a dinner to taste what has been prepared.
Make sure you leave some time to check out the wonderful and renowned fashion boutiques that have inspired many a runway outfit.
Day 4: Milan to Naples
Today you’ll head to Naples via high-speed train which takes about four hours.
When you arrive, you’ll be met by your driver who will take you to your hotel in beautiful Sorrento.
Try authentic Italian pizza at a beautiful local restaurant – it’s guaranteed to taste better because you’re in Italy!
Day 5 and 6: Sorrento and the Amalfi Coast
In the morning you’ll set off to the Amalfi Coast by private car. You’ll stop in Positano and Amalfi. During the trip, make sure you try a typical Caprese Sandwich to experience the real atmosphere of the Coast.
The Amalfi Coast’s shoreline is rugged with sheer cliffs and small beaches augmented by quaint fishing villages with many a brightly coloured property.
There’s a reason that the coastline is known by UNESCO as a World Heritage site because it is an oustanding example of a Mediterranean landscape. You’ll also see beautiful lemon groves, sumptuous vineyards and plenty of vast villas.
Day 7: Pompeii
In the morning, you’ll drive to Pompeii. You’ll take a guided tour of the famous archaeological site, to discover the unique remains of the city destroyed by the eruption of Vesuvius in AD 79.
The city was buried under metres of ash and pumice but the city was preserved despite killing all in its wake.
The afternoon will see you return to Naples for a walking tour where you’ll try some famous typical street food like “panzerotti”, “zeppole” or the “cuoppo di pesce fritto” (fried fish). Visits to Plebiscito Square, Umberto I Gallery, Maschio Angioino and other wonderful locations.
After the stroll, you’ll head to Rome by high-speed train.
Day 8 to 10: Rome
In the morning, you’ll meet your guide for a walking tour of Ancient Rome to take a gay friendly walking tour of Ancient Rome to discover the Colosseum and the Imperial Fora. Make sure to have lunch at Coming Out, the cafe bar that is an institution in Rome’s gay scene.
In the late afternoon you’ll take another cooking class. You will learn how to prepare Italian meat or desserts. You’ll then have the chance to eat what has been prepared.
Your final day is yours to explore the city further. Perhaps visit Vatican City, shop in the boutiques and backstreets of Rome or simply relax. We can, of course, arrange further private guides to ensure you get the best out of your time in Rome.
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 specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, 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 personalized 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 traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, 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, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
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 personalized 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+ travelers 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 traveling 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 inquiry to homecoming. No call center, and nothing is charged until you decide to book.