Sometimes you only have a short window to get away and so you want to ensure you use your time efficiently. Our gay city break itineraries are more than just a hotel and a flight. In them, you’ll find that we usually arrange transport to and from the airport alongside interesting excursions, private tours or restaurants on offer in the city. At Out Of Office we know that time is precious and so let us sort the arrangements for you.
Once you have browsed our site for inspiration, let us know your requirements and one of our travel concierge team will be in touch with you to build the perfect gay city break itinerary for you. If you’re looking to travel to multiple cities on the same itinerary we can help you with that too.
Featured Gay City Breaks
AustriaBudapest, Vienna And Prague
From 9 days - Tailor-made from £3100See the cultural sites of Central Europe’s great cities. Over nine days you’ll explore Buda and Pest, the two distinctive halves of Budapest. You’ll also see the imperial splendour of Vienna and the fairytale streets of Prague. These cities are...View Itinerary- France
Experience London And Paris
From 7 days - Tailor-made from £1795You haven’t “done” Europe until you’ve acquainted yourself with its two most influential cities. In London, you’ll see everything from Buckingham Palace to the bustling streets of Soho. Paris is only a short train ride away. In the French capital,...View Itinerary - Thailand
Bangkok, Chiang Mai and Chiang Rai
From 10 days - Tailor-made from £1995This luxury itinerary takes in three of Thailand’s best-known destinations – Bangkok, Chiang Mai and Chiang Rai. Staying in the beautiful Anantara Resorts, you’ll find luxury and exquisite service. Spend time in Bangkok getting under the skin of Thailand’s capital...View Itinerary
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.
Most Popular Gay City Breaks
Tailor-MadeMaltaA 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...
Tailor-MadeSouth AfricaBoutique Cape Town and Wine Region
The itinerary is perfect if you’re looking for a more boutique experience of South Africa staying in two of the country’s finest boutique hotels. Spending five days at the luxurious and small Kensington Place on the slopes of Table Mountain,...
Tailor-MadeAustraliaExplore Sydney
Sydney – undoubtedly one of the greatest new cities on earth with its slew of beaches and incredible modern architecture. This short city itinerary is perfect for those of you wanting to stop over in Sydney and have free time...
Tailor-MadeGreeceDiscover 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...
Tailor-MadeItalyNaples and Amalfi Coast
Discover magical Italy in this incredible tour that takes in Naples, Pompeii and the island of Capri. Staying in beautiful accommodation you’ll visit some of Italy’s most beautiful towns, cities and the stunning island of Capri. See Pompeii which Mount...
Tailor-MadeUnited KingdomLondon and Edinburgh
Explore two of the UK’s most vibrant cities. Spend five days in London, where you will tour around some of its most famous tourist spots including Tower Bridge, The Houses of Parliment and Buckingham Palace. Head out onto the Thames...
Tailor-MadeUSANew York To Washington DC
This is your chance to experience America’s most iconic cities, New York and Washington DC. New York is arguably the most exciting city in the world. It’s certainly the most recognisable as it’s been the setting for so many famous...
Tailor-MadeGermanyDiscover Germany
From Berlin to the Black Forest, this is your chance to discover Germany. Your adventure will begin in Berlin, one of the coolest cities in the world. Its fascinating history is there to be discovered and its nightlife is arguably...
Tailor-MadeMykonosLondon, Barcelona And Mykonos
See the cultural sights of two great European cities and then unwind on an idyllic Greek island. This will make for an ideal mix of culture and relaxation. In London, you’ll see Shakespeare’s Globe and The Crown Jewels. You’ll also experience...
Tailor-MadeUSABoston and Provincetown
Pair up Boston and Provincetown on a Massachusetts adventure. Spend a few days exploring Boston and its rich history, then head to Provincetown for a beautiful seaside escape – a particularly gay-friendly destination. Either take a ferry between the two...
Tailor-MadeMaltaCultural Malta
Malta is known as one of the most gay-friendly countries on earth. Renowned for its historic sites, it has been ruled by the Romans, French, British, Moors and the Knights of Saint John. As a result, you’ll find a great...
Tailor-MadeFranceLondon, Paris And Berlin
Discover the three major capital cities of Europe. There is so much history and culture to discover it can be overwhelming. This itinerary will ensure that you see the major sights, taste the best food and learn about three countries...
Tailor-MadeSpainMadrid, Seville, Valencia and Barcelona
Experience the best that Spain has to offer by visiting its main cities and regions – Madrid, Seville, Valencia and Barcelona. This eight-day trip includes 4* hotels and many activities that will get you into the swing of Spanish life....
Tailor-MadeSpainBarcelona And Madrid
There’s so much to see in Spain – it’s one of the world’s most visited countries. Exploring its two biggest cities is a great way to discover it. You’ll see the great masterpieces of Gaudi, stroll down Las Ramblas and...
Tailor-MadeChinaBeijing to Shanghai
Start in Beijing and explore this vibrant dynamic bustling city. You will visit the iconic great wall of China and the Forbidden city. Then head to Xian where you will visit the famous Terracotta Warriors and take a stroll through...
Tailor-MadeTaiwanHighlights of Taiwan
Taiwan is a country of extraordinary beauty – from its beautiful landscapes to its towering mountains to the famous Sun Moon Lake. Taroko’s stunning limestone gorges plunge deep whilst at Sun Moon Lake you’ll feel at one with nature as...
Browse Itineraries
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.
