North America
Luxury North America Holidays
Suggested trips through North America, each one a starting point that our LGBTQ+ travel specialists tailor around your dates, pace and preferences.
Most begin in the USA, Costa Rica, Canada and Bermuda, and many combine more than one country.
Featured Holidays in North America
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 Marketplace, and stroll along the Boston Harbor.
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Whales, Bears and Vancouver Island
Embark on an unforgettable journey through the pristine landscapes and captivating culture of western Canada with this meticulously curated itinerary. Over the course of nine days, travellers will immerse themselves in the diverse ecosystems and vibrant communities of Vancouver Island and the mainland.
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Miami and Puerto Rico
Experience the epitome of luxury with our exclusive twin-centre itinerary, featuring two of the USA's premier destinations: Miami and Puerto Rico. These vibrant locales offer a captivating blend of dazzling splendor and stunning coastal landscapes, making them perfect for discerning travellers seeking an unforgettable getaway.
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Mardi Gras 2025 In New Orleans
Tailor-made HolidayNew Orleans is one of the most enigmatic cities in America. It's the home of voodoo, jazz, and Mardi Gras. Anne Rice set her famous vampire novels here for a reason. It's every bit as spooky as it is romantic. The biggest event of the year in New Orleans is, of course, Mardi Gras. It begins on "the 12th night" and ends on "Fat Tuesday (the Tuesday before Ash Wednesday).
8 days tailor-made from £2,455 per person View trip
New York And New England
Tailor-made HolidayExperience the thrill of embarking on an unforgettable journey from the vibrant streets of the "city that never sleeps" to the picturesque landscapes of New England, a region steeped in the history of the American Revolution. This self-drive adventure promises to immerse you in the essence of the USA, from the iconic cityscape of Boston to charming hamlets like Jackson.
17 days tailor-made from £4,950 per person View trip
Napa Valley Wine Tour
Tailor-made HolidayThe Napa and Sonoma Valleys, just over an hour from San Francisco, are prime destinations for wine enthusiasts. This region, known for its world-class vineyards, is ideal for private groups or company incentive travel. The itinerary includes visits to both boutique family-run wineries and well-established brands. Guided tours by local experts offer extensive wine knowledge, coupled with ample tasting opportunities.
8 days tailor-made from £3,555 per person View trip
New York To Washington DC
Tailor-made HolidayEmbark on a once-in-a-lifetime journey to explore two of America’s most iconic cities - New York and Washington DC - on this amazing twin-centre itinerary. New York stands as a beacon of excitement and innovation, captivating visitors with its towering skyscrapers, bustling streets, and world-renowned landmarks. From the dazzling lights of Times Square to the serene beauty of Central Park, every corner of the city pulsates with energy and charm.
8 days tailor-made from £2,500 per person View trip
Las Vegas and the Canyons
Tailor-made HolidayEmbark on an unforgettable 10-day self-drive journey that beautifully blends the natural wonders of Nevada, Arizona, and Utah with the dazzling allure of Las Vegas. Your adventure begins in the world-renowned Sin City, where you can indulge in its vibrant nightlife, luxurious resorts, and endless entertainment options.
10 days tailor-made from £1,360 per person View trip
Walt Disney World Florida
Tailor-made HolidayBring 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 dream Disney getaway. With a great selection of hotels on offer and a Disney park that will grant every wish, your holiday will be one you will never forget.
8 days tailor-made from £1,330 per person View trip
New England: Boston, Maine and Connecticut
Tailor-made HolidayDiscover the captivating allure of New England, USA, a region renowned for its rich heritage, majestic forested mountains, and breathtaking Atlantic shoreline. Immerse yourself in the storied past of Boston as you traverse the iconic Freedom Trail, tracing a path through centuries of history amidst the cobblestone streets and historic landmarks of one of America's oldest cities. Next, you'll unveil the charm of Coastal Maine.
8 days tailor-made from £1,560 per person View trip
Miami and Fort Lauderdale
Tailor-made HolidayEmbark on a journey of discovery as you delve into the rich tapestry of Fort Lauderdale and Miami. Embrace the spirit of inclusivity that permeates these dynamic cities, where diversity is celebrated, and everyone is embraced as part of the community. With their cosmopolitan charm and endless array of attractions, Fort Lauderdale and Miami make for a fantastic twin-centre itinerary for LGBTQ+ travellers.
10 days tailor-made from £1,360 per person View trip
Luxury Hawaii Island Hopping
Tailor-made HolidayEmbark on an unforgettable journey to the enchanting Hawaiian islands, where you'll delve into the unique charm of Honolulu and Kauai, each offering a distinct tapestry of culture, adventure, and natural beauty. Immerse yourself in the rich cultural heritage of these tropical paradises as you indulge in an array of once-in-a-lifetime experiences.
13 days tailor-made from £3,375 per person View trip
Gay Wedding
Hawaii Wedding and Honeymoon
Tailor-made HolidayAre you dreaming of exchanging vows on the sun-kissed shores of Maui, the jewel of Hawaii? Look no further than Out Of Office to turn your wedding dreams into reality. Our expert team specialises in crafting bespoke wedding experiences tailored to suit you and your beau's dreams. Imagine saying "I do" on the pristine sands of Poolenalea Beach, a secluded paradise nestled in the breathtaking landscapes of Wailea.
7 days tailor-made from £5,005 per person View trip
Florida Keys Island Hopping
Tailor-made HolidayEscape to the enchanting allure of the Florida Keys, a mesmerising archipelago boasting some of the most captivating tropical islands in the USA. Situated just off the coast of Miami, these islands beckon travellers with their unique charm and rich history. Each island in the Florida Keys boasts its own distinct ambiance and array of experiences.
12 days tailor-made from £2,465 per person View trip
Miami and Key West
Tailor-made HolidayEmbark on a remarkable journey with our exclusive twin-centre USA itinerary to Miami and Key West, offering the quintessential American experience of sun, beaches, and relaxation. Begin your adventure with three unforgettable nights in dynamic Miami, known for its vibrant culture and stunning beaches. Then, head south to the tropical paradise of Key West for an additional four nights of pure bliss.
8 days tailor-made from £1,345 per person View tripGay Group Trips in North America
Set departures with dates already fixed, organised end to end and travelling as a small group. Where a departure is full, dates are available on request. Extensions either side can be added, and we can plan something tailor-made instead if you would rather.
Reading on North America
The Underrated Luxury of Greater Miami
From the art-deco glamour of Miami Beach to the sprawling properties found in Coconut Grove, Greater Miami & Miami Beach is one of the USA’s best destinations for luxury travel and is home to an array of once-in-a-lifetime experiences.
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The Top 5 Most Exciting Destinations in Costa Rica
Costa Rica translates to rich coast, a suiting name for this charming small country situated south of Nicaragua and north of Panama. Also known as the happiest place on earth to live by happy index and the land of Pura Vida which translates to pure life. This is a common saying you will hear repeatedly in Costa Rica and for many, it is a way of life.
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Canada’s hidden gem – Prince Edward County
Our founder Darren Burn travelled to Canada with his partner for a week-long road trip to Montreal, Prince Edward County, Toronto and Niagara Falls. In part two he took the drive from Montreal to quaint Prince Edward County. Leaving Montreal downtown, we set off on a fairly lengthy drive (by British standards at least) to Prince Edward County.
ReadStellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
We plant trees for every booking
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.
We donate to Rainbow Railroad with every booking
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.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of travelling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first enquiry to homecoming. No call centre, and nothing is charged until you decide to book.