Luxury Gay Sailing and Cruises vacations

Gay Sailing and Cruises

If you are keen to visit several locations in one trip, then the multi-port nature of our gay sailing and cruise holidays could be just what you are after.

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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Out Of Office has a selection of gay sailing and gay cruise destinations around the world, all with multiple departure date options throughout the year, encouraging you to meet new people and create memories to last a lifetime.

From river cruises and island hopping on yachts to luxury round-the-world cruises, all the cruise lines we work with are gay-friendly, welcoming, and inclusive to all. Most of our itineraries feature extended time in each port and overnight stays in our most popular destinations, allowing you to make the most of your evenings.

We proudly feature cruises with Seabourn and Virgin Voyages. These luxurious cruise lines elevate the experience with their exclusive services and top-tier amenities, ensuring a journey of comfort and style. Seabourn's intimate ships and Virgin Voyages' vibrant, modern approach both offer unique ways to explore the seas. With them, you'll find yourself indulging in the highest standard of hospitality and entertainment whilst on board, as well as visiting some incredible destinations around the world.

As with all our gay sailing and cruise holidays, the journey is as important as the destination, so you will experience exceptional food and entertainment whether you are on board or in port.

To plan your ideal gay sailing and cruise vacation itinerary, contact a member of our sales concierge team today.

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Mykonos & Santorini Private Group Getaway
Mykonos & Santorini Private Group Getaway


Embark on an exquisite journey through the enchanting islands of Greece on this private group getaway. Over seven days, your group will experience the epitome of Grecian elegance, from the vibrant charm of Mykonos to the majestic beauty of Santorini....

Italy & Dalmatian Coast Cruise
Italy & Dalmatian Coast Cruise


Embark on a luxurious sojourn that gracefully intertwines the enchanting allure of Italy with the pristine beauty of the Dalmatian Coast on this fabulous tailor-made itinerary and Seabourn cruise. Your journey begins in the storied waterways of Venice, where you’ll...

Northern Europe Voyage
Northern Europe Voyage


Embark on a luxurious Northern Europe voyage that seamlessly combines the historical splendor of London with the untouched natural beauty of Scotland and Iceland. Your journey begins in the bustling heart of London, staying at the iconic Claridge’s Hotel, where...

Journey Around the Mediterranean
Journey Around the Mediterranean


Set sail on a captivating cruise adventure that weaves the historical charm of Athens with the serene beauty of the sparkling Mediterranean. This journey invites you on an exciting exploration that’s as culturally enriching as it is luxurious. Your adventure...

Romantic Italy & Greek Islands Cruise
Romantic Italy & Greek Islands Cruise


Embark on an unforgettable European journey to discover the captivating beauty of Italy, Greece, and Turkey on this meticulously crafted itinerary. This luxurious voyage includes a seven-night cruise of the Greek Islands, courtesy of Virgin Voyages, so you can seamlessly...

Miami & Caribbean Cruise
Miami & Caribbean Cruise


Escape on an alluring journey to Miami, Costa Maya, and the Bahamas on this luxury Miami and Caribbean cruise itinerary. Experience Miami’s exhilarating energy before retreating to the Caribbean Sea’s tropical serenity on this luxurious tour. You’ll begin your indulgent...

Best Sailing And Cruise Holidays

We love a sailing trip. Being pampered on board as you sail from glamorous destination to another is the way to go. One of our favourite sailing destinations is the Greek islands. You can even combine an Aegean cruise with a trip to Bodrum on Turkey’s Mediterranean coast. The Greek islands have so much to offer, from more tranquil islands like Naxos to the gay party island of Mykonos, one of the best gay destinations. Cruising from island to island is the best way to discover the charms of the Cyclades: it’s an unbeatable destination for a Mediterranean cruise.

A Mediterranean cruise is always a good idea. Explore some of the best cities and towns of the Old World as you sail on a clipper yacht. A Rhine River cruise through the Netherlands and Germany is also a popular choice. Supposing you’d like to go for something a little more adventurous, a luxury cruise into the Amazon jungle may be in order: you can explore one of the world’s most intricate ecosystems and even encounter tribes who’s customs remain unchanged for many centuries. Naturally, we only work with the most gay-friendly cruise providers.

Luxury cruise lines such as Virgin or Seabourn are also sensible choices for those who like a luxury cruise. Whilst not exclusively gay, they both offer excellent welcomes for LGBT clients on board. Other cruise lines that are particularly LGBT friendly are Celebrity Cruises, Norwegian and Cunard.

Star Clipper
Star Clipper Greece

Star Clipper

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Sailing in the Maldives gives you a chance to explore multiple islands. Most Maldivian islands are so small they can only fit one resort. You’ll get to see many of the highlights of the Maldives in one trip if you opt for a cruise. A luxury cruise on board a floating spa is one of our preferred options for a Maldives cruise. As there’s no industry in the Maldives, the water is crystal clear. It’s a great destination for water sports and marine life, so you can keep active in between trips to the spa and the beach.

We have a diverse range of cruises available, including a number of gay group cruises. These include luxury trips on board world-class cruise ships and also more budget-friendly catamaran trips. Joining a sailing trip of the Caribbean islands or even French Polynesia gives you a considerable advantage: it’s very tricky to organise such a sailing trip yourself and see so much in such a short space of time. Joining a cruise means you just have to sit back and relax. All of the hard work has been done in advance by destination experts.

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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

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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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