Tailor-made Vacation · Italy
Best Luxury Hotels in Italy for Gay Travelers
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At a glance
Italy is home to some of the most extraordinary hotels in the world.
Stay at one of the Amalfi Coast’s most glamorous cliffside hotels, wake up on a private island in the Venetian Lagoon overlooking St. Mark’s, or sleep inside a historic palazzo in Matera, Italy’s mysterious city of caves.
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Further north, you can retreat to the shores of Lake Como, stay among the grand villas of Florence, or check into one of Milan’s most luxurious addresses.
Italy has been one of Out Of Office’s most booked European destinations for years, and over that time we have built up a very clear view of the hotels that consistently deliver.
This is a highly curated selection: the properties our travelers return to, the hotels we recommend for honeymoons and weddings, and the places we trust for anniversaries, milestone birthdays and once-in-a-lifetime trips.
Some are grand Italian icons. Others are more boutique properties that become the highlight of the journey.
All have been chosen because they offer the level of service, setting and experience we expect for our travelers.
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.
Il San Pietro di Positano
Carved into the cliffs just outside Positano, Il San Pietro is one of the Amalfi Coast’s most glamorous and discreet hotels.
Its combination of privacy, extraordinary sea views and old-school Italian glamour has made it a favorite with high-profile guests including George Clooney and Julia Roberts. Yet despite its international reputation, the hotel remains family-run, having been created by Carlo Cinque in the 1970s.
Terraces tumble toward the Mediterranean, the setting feels wonderfully removed from the crowds of Positano, and the whole property has a sense of occasion from the moment you arrive.
For honeymoons, anniversaries and milestone trips on the Amalfi Coast, this is one of the hotels we return to again and again.
Villa Cora
If you’re looking for something very grand, then Villa Cora in Florence could be the answer. This is a very ornate property. It’s so luxurious it kind of goes beyond luxury: this is how Marie Antoinette would have lived if she’d had the budget.
Villa Cora overlooks the Boboli Gardens from the hills just outside Florence’s historic center. Commissioned by Baron Oppenheim in the 1860s, the villa has hosted major figures including Tchaikovsky and Napoleon’s wife.
The interiors are a dizzying mix of styles: trompe l’oeil frescoes, crystal chandeliers, parquet floors and lavish salons, all surrounded by rose gardens.
Villa Cora became a Grand Hotel in the 1960s and remains particularly popular for weddings. Today, it is considered one of Florence’s most remarkable historic buildings and one of Italy’s standout independent luxury hotels.
Mandarin Oriental, Milan
If you’re planning a luxury trip to Milan, Mandarin Oriental is a great choice. Combining Milanese design with Oriental luxury, the hotel places you in the heart of the fashion capital of the world. Boasting famous fans including Dame Helen Mirren and Christian Louboutin, Mandarin Oriental has an unrivalled reputation for service and attention to detail, helping you feel at home from the moment you arrive.
You can indulge in soothing spa treatments that specialize in both Eastern and Western therapies, or enjoy a two-Michelin-starred meal at the hotel’s restaurant. Surrounded by 1940s Milanese interior decor, it’s hard not to fall for the glamour of Mandarin Oriental.
Palazzo Gattini
Matera is one of Italy’s most extraordinary cities and one of the oldest in the world. Its ancient stone streets and cave dwellings have stood for thousands of years, creating a landscape so dramatic that Matera has often been used as the backdrop for biblical films.
Yet the city is far from frozen in time. Today, Matera is filled with stylish restaurants, boutique hotels and contemporary design, much of it built directly into the ancient stone.
Palazzo Gattini sits in one of the city’s most prestigious locations, beside the cathedral and overlooking the Sassi cave dwellings below. This was the part of Matera where the aristocracy built their homes during the Renaissance, and the palazzo still has a commanding presence over the old city.
From here, you look out across caves and stone houses that have been inhabited since the Stone Age. It’s one of the most remarkable hotel settings anywhere in Italy.
Cipriani, A Belmond Hotel, Venice
Cipriani is the last word in Venetian glamour. Set on Giudecca overlooking the lagoon, it feels wonderfully removed from the crowds, yet St. Mark’s Square is only a few minutes away by boat.
The hotel was founded in 1958 by Giuseppe Cipriani, the man behind Harry’s Bar and the Bellini, and it has been drawing royalty, Hollywood stars and the international jet set ever since. Rooms and suites are classic Venetian in style, with views across either the lagoon or the hotel’s manicured gardens.
There is a Michelin-starred restaurant, Oro, and an enormous saltwater swimming pool – a rarity in Venice. And given the hotel’s history, a Bellini on the terrace overlooking the lagoon is practically compulsory.
Mandarin Oriental, Lake Como
This is the place to be if you’re staying around Lake Como. It’s a 19th-century villa once inhabited by a grand opera diva with an unimprovable name, Giuditta (“Judith”) Pasta. Ms Pasta was clearly a lady of considerable refinement. When it emerged as a hotel it was called CastaDiva Resort, but the property really came to life when it was taken over by Mandarin Oriental.
The decor is chic and contemporary. The wallpaper is even handmade. Mandarin Oriental, Lake Como is also frequented by Hollywood royalty and it has the price tag to match. This is a great choice if you’re looking for something romantic and luxurious on a very special occasion. The hotel is located close to the village of Blevio.
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.
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Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
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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.
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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.
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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.
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