Luxury Gay city breaks vacations

Gay city breaks

Sometimes time is short and getting the most from your gay city break means leaving the organizing to someone else. At Out Of Office, we know time is precious, so we sort all the arrangements, leaving more time for you to enjoy your gay city break getaway.

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Our gay city break itineraries are more than just a flight and hotel. We can also arrange transport to and from the airport, thought-provoking excursions, customized private tours, and bookings for the latest must-visit restaurant.

From cosmopolitan to romantic, historic to cultural, we can help you choose a getaway to remember in cities across Europe, Africa, Asia, Oceania, South America, and North America. We can even combine multiple cities on one itinerary, helping you to really optimize your vacation.

To plan your perfect gay city break, contact a member of our sales concierge team today.

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...

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...

Other Short Break Trips

Ultimate Luxury: Italy
Ultimate Luxury: Italy


Experience the highlights of Italy in unmatched luxury on this fully customizable 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...

Gay Group Trip: Basel to Amsterdam Pride River Cruise
Gay Group Trip: Basel to Amsterdam Pride River Cruise

Group Trip

Spend a week exploring one of Europe’s great rivers, sailing from Switzerland through France, Germany and then Holland. The trip will end in Amsterdam in time for Amsterdam Pride with its famed Canal Boat Parade. You’ll see all the highlights...

Travel With Pride: The Venice Simplon-Orient-Express 2023
Travel With Pride: The Venice Simplon-Orient-Express 2023

Group Trip

Hop on board The Venice Simplon-Orient-Express and take a trip to a more glamorous time. The shimmering vintage carriages of the train bring to life the golden age of luxury train travel. It took considerable craftsmanship to restore these trains...

Discover Athens
Discover Athens


Discover Athens in this four-day itinerary which takes in the incredible history and architecture of the city, including the Acropolis. Staying in ultimate luxury at one of Athens’ best hotels, you’ll get under the skin of the culinary scene by...

A Long Weekend In Malta
A Long Weekend In Malta


Malta is a small island country that boasts excellent weather, clear blue waters and vibrant ancient history. You’ll find the world’s oldest prehistoric temples, Roman ruins and Medieval buildings. One of the most densely populated countries in the world, Malta is...

Walt Disney World Florida
Walt Disney World Florida


You have dreamed about going, well we can make that dream a reality. Bring your childhood memories to life and step into the magic at Walt Disney World Resort Florida. With a great selection of hotels on offer, and a...

Best City Break Hotels

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020 7157 1570


To start planning your trip, please call us or complete the enquiry form and one of our team of experts will contact you as soon as possible for an initial consultation to discuss your travel plans in more detail.

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
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