Luxury Gay City Breaks vacations

Gay City Breaks

In our fast-paced world, maximizing the enjoyment of your limited holiday time is crucial, especially when it comes to gay city breaks. At Out Of Office, we understand that your time is invaluable

Here at Out Of Office, we truly understand the world you live in, and the world you want to explore. Our attention to detail, exceptional service and deep understanding of both luxury travel and LGBTQ+ travel make us a fantastic choice for those looking for a travel experience where exclusivity meets inclusivity.

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We handle all the logistics and arrangements for your city break, allowing you to focus solely on making the most of your getaway. Our comprehensive approach to planning means that every minute of your trip is optimized for enjoyment and discovery.

Our gay city break itineraries offer much more than just flights and hotel bookings. We provide seamless transport solutions to and from the airport, ensuring a hassle-free start and end to your trip. But the experience doesn’t stop there. We carefully curate thought-provoking excursions and customized private tours, allowing you to delve into the unique character and hidden gems of each city. And for the epicurean traveller, we secure bookings at the latest must-visit restaurants, ensuring that your culinary experiences are as memorable as your adventures.

Whether you're drawn to the vibrant and cosmopolitan streets of Europe, the romantic allure of historic cities in Africa, the diverse cultural tapestry of Asia, the unexplored treasures of Oceania, the spirited rhythms of South America, or the varied landscapes of North America, we have the expertise to guide you to your ideal destination. Our flexibility even allows for the combination of multiple cities in one itinerary, perfect for those looking to enrich their holiday with a variety of urban experiences. To embark on a meticulously planned gay city break that caters to your preferences and maximizes your time, we invite you to connect with one of our skilled luxury travel experts. They are dedicated to crafting an unforgettable city adventure tailored just for you.

World's Best Gay Cities
Recommended Reading
World's Best Gay Cities

We have come a long way since the dark days of the Stonewall Riots in NYC. This event was started by LGBT+ people (notably LGBT+ people of colour) who resisted police brutality, intimidation and harassment and is often cited as...

More Suggested Short Break Trips

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Private Countryside Castle Getaway
Private Countryside Castle Getaway


Discover our private castle or manor house group getaway, designed to cater to those seeking an extraordinary luxury group holiday. Over four days, your journey will unfold amidst the historic elegance of grand properties in Scotland and England, each offering...

Ultimate Luxury: Italy
Ultimate Luxury: Italy


Experience the highlights of Italy in unmatched luxury on this fully customisable Ultimate Luxury itinerary. Designed for indulgence, every detail elevates your journey through Italy’s most captivating destinations: the sparkling and serene Lake Como, the rolling vineyards of Tuscany, historic...

A Long Weekend In Malta
A Long Weekend In Malta


Indulge in the allure of Malta, a captivating island nation nestled in the Mediterranean Sea, where pristine weather, azure waters, and a rich tapestry of ancient history await. Explore the world’s oldest prehistoric temples, marvel at Roman ruins, and wander...

Walt Disney World Florida
Walt Disney World Florida


Bring your childhood memories to life and step into the magic at Walt Disney World Resort Florida. Whether you’re looking for a Disney family holiday or you’re a big kid looking to fulfill your childhood dreams, we can create your...

Boston and Provincetown
Boston and Provincetown


Embark on a captivating Massachusetts adventure, starting in the historic city of Boston. Spend a couple of days exploring Boston’s rich history, particularly its pivotal role in the American Revolution. Walk the famous Freedom Trail, visit the historic Faneuil Hall...

Bangkok and Ko Samet
Bangkok and Ko Samet


Combining the city of Bangkok with the nearby island retreat of Ko Samet is the ideal way to enjoy both city and beach in Thailand without flying down to the south of the island. Just three hours from Bangkok, Ko...

Best City Breaks

London is home to more active Grindr users than any other city, making it – in numerical terms! – the world’s gayest city. It’s also one of the most exciting and cosmopolitan cities in the world. The UK’s vast capital has a buzz that’s arguably matched only in New York City. London was originally founded by the Romans nearly two-thousand years ago. You can spend a lifetime exploring London and never run out of new places to discover.

Just over the channel you’ll find gay Paris, the City of Lights. By the middle of the nineteenth century, Paris was considered to be the most sophisticated city on earth. It dominated in terms of cuisine, fashion and art. In many ways, Paris has clung onto its crown ever since. Although the reality of Paris is more rough and ready than the picture-postcard image, it’s an impossibly romantic city with great nightlife and just about any else you possibly desire.

Le Marais


A Gay Guide To Palm Springs

Palm Springs is a chic desert oasis in the Coachella Valley. It’s been a glamorous destination since the heyday of Golden Age Hollywood. The major contract players were obliged to stay close to their studios and Palm Springs, just a...

A Gay Guide To Sitges

Sitges is a picturesque coastal town on the Costa Brava. It’s just a half-hour train ride away from Barcelona and it has some of the best gay beaches in Spain. Long a haven for artists, it’s now known as the...

Our Favourite Gay City Breaks

Lisbon is the most up and coming city in Europe. It’s undergone something of a boom in recent years. Lisbon still retains its faded charm but it’s rapidly gentrifying. Go see it while it still retains this old school charm and while the night away on a dreamy Fado club.

If you’re looking for a hidden gem you should definitely consider Taipei. It’s a big, brash city with loads of culture, great nightlife and it hosts Asia’s biggest gay pride festival. Compared to Tokyo and Shanghai, Taipei isn’t a big destination for tourists. That will no doubt change in the coming years. Taipei is full of hidden charms.

A twin-centre city break gives you the best of both worlds. You get the buzz of a big city and then the more tranquil environment of a smaller town. Combining Lisbon with the charming town of Sintra is a must. A perennial favourite for Out Of Office travellers is it combine Barcelona and Sitges. Both towns are just a short train ride away from the big city.

Washington D.C.
Jefferson Memorial

Washington D.C.

Our Gay Guide To Bogotá

One of our concierge team, Jaike Rowe, has just returned from a trip to Peru and Colombia. Here he writes about the best things to do in Bogotá. I recently had the opportunity to take the most incredible trip to...

A City Guide To Puerto Vallarta

Puerto Vallarta is one of the most popular tourist destinations in Mexico. The big attractions are the white sand beaches, chic hotels, buzzing nightlife and excellent gastronomy. It’s considered to be a top foodie destination in Mexico, second only to...

Best City Break Hotels

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Why book with us?

Personal Service

We want to ensure you have the best experience with us so we’ll keep working on your itinerary until perfect. You will have your own personal dedicated member of our team who will help build the perfect trip for you.

Call our travel experts on +44 (0)20 7157 1570

Our 5* Reviews

We pride ourselves in the number of clients that are referred to us by our existing customers. Our 5* Trustpilot rating is important to us, so we encourage you to browse our reviews. They speak for themselves and that's why you are in safe hands.

Make an enquiry


020 7157 1570


To start planning your luxury trip, tell us more about your travel plans and we'll match you with one of our experienced travel specialists. You can speak to us via phone, email or video call.

All the prices on our website do not include flights. We can, of course, arrange them for you.

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  • $2,000-3,000
  • $3,000-5,000
  • $5,000-7,500
  • $7,500-10,000
  • $10,000+