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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Luxury New Mexico: Santa Fe, Los Alamos & Breaking Bad Locations
Tailor-made HolidayNew Mexico doesn't look like anywhere else in America, and it doesn't feel like it either. The light is different, the landscape is different, and the culture, shaped by centuries of Native American, Spanish colonial, and Anglo-American layering, sits apart from anything on the coasts. This itinerary runs three threads simultaneously.
8 days View trip
Eco-Friendly Costa Rica
Tailor-made HolidayEmbark on an unforgettable journey with our wide-reaching and ultra-luxury eco-friendly Costa Rica itinerary, designed to immerse you in this of diverse country while minimizing your environmental impact. Spanning the breadth of Costa Rica's unique landscape, you'll explore verdant coffee plantations, pristine nature reserves teeming with wildlife, charming historic cities, and some of the world's most stunning coastal environments.
8 days tailor-made from £3,940 per person View trip
The Ritz-Carlton Yacht Collection
Tailor-made HolidayThe Ritz-Carlton Yacht Collection operates three custom-built superyachts delivering hotel-level service in yacht-sized vessels. These ships accommodate 298-448 guests (depending on vessel) in all-suite configurations, positioning between traditional luxury cruises (1,000+ passengers) and true private yachts. The experience mirrors staying at a Ritz-Carlton property that happens to move between ports, with consistent service standards, suite-style accommodations, and dining that doesn't rely on buffets or regimented seating times.
7 days View trip
Costa Rica Family Adventure
Tailor-made HolidayEmbark on an unforgettable journey through Costa Rica, where your family will experience thrilling wildlife encounters, breathtaking landscapes, and immersive cultural experiences. From exploring misty rainforests and spotting sloths in the treetops to learning to surf on golden beaches, this itinerary balances adventure and relaxation, ensuring every member of the family has a magical experience. Your adventure begins in Tortuguero National Park, a remote jungle paradise accessible only by boat.
11 days tailor-made from £4,200 per person View trip
LGBTQ+ Greater Palm Springs & WeHo Getaway
Tailor-made HolidayThis luxurious ten-day escape offers LGBTQ+-friendly experiences in two of the most welcoming cities in the United States. Designed for those who appreciate both the finer things in life and a rich, welcoming community, this itinerary promises an unforgettable exploration of Palm Springs’ and Los Angeles' unique heritage and contemporary gay scene. Begin your stay at the iconic Kimpton Rowan Hotel, perfectly positioned in the heart of Palm Springs.
12 days tailor-made from £4,920 per person View trip
Costa Rica Family Escape
Tailor-made HolidayEmbark on an unforgettable journey through the heart of Costa Rica with our bespoke luxury family itinerary, designed to deliver both exhilarating adventure and pure relaxation. Over nine days, this tailor-made experience will take you from the awe-inspiring Arenal Volcano to the serene beauty of Manuel Antonio, and is ideal for families seeking an extraordinary Costa Rican adventure.
9 days tailor-made from £3,200 per person View trip
Outdoor Adventures in Palm Springs & San Diego
Tailor-made HolidaySet off on a sumptuous outdoor adventure in the stunning landscapes of Greater Palm Springs and San Diego with our luxury itinerary. This nine-day escape is designed for those who crave both relaxation and adventure, set against the backdrop of the majestic desert scenery that typifies Palm Springs, and the ocean views that San Diego is famed for.
12 days tailor-made from £5,315 per person View trip
A Different Costa Rica
Tailor-made HolidayExperience the splendour of Costa Rica's diverse landscapes and wildlife with our carefully crafted Costa Rica holiday itinerary, showing you a lesser-travelled side of this stunning country. Embark on a journey through some of the most iconic destinations in this beautiful country, starting with the breathtaking Central Valley.
13 days tailor-made from £2,960 per person View trip
So-Cal Triangle: LA, San Diego, Greater Palm Springs
Tailor-made HolidayEnjoy a grand Southern California tour that epitomizes the luxury, diversity, and vibrancy of this iconic region. From the sun-kissed beaches of Santa Monica to the glamorous streets of West Hollywood, and from the lively scenes of San Diego to the serene desert oasis of Greater Palm Springs, this 14-day itinerary offers an exquisite blend of cultural richness, natural beauty, and indulgent experiences.
14 days tailor-made from £4,590 per person View trip
Miami & Caribbean Cruise
Tailor-made HolidayEscape 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 Miami and Caribbean holiday at Nobu Hotel Miami Beach, a sophisticated beachfront urban oasis ideally located in the heart of Miami Beach.
9 days tailor-made from £5,550 per person View trip
Miami: The Out Of Office Collection
Tailor-made HolidayMiami remains a standout among the world's most sought-after holiday spots, and for good reason. The city's inviting climate caters perfectly to sun chasers, while its myriad of vibrant neighbourhoods offers a rich tapestry of experiences waiting to be explored. From the tranquil elegance of Coconut Grove to the vibrant energy of Miami Beach, the city promises an endless array of possibilities for every type of traveller.
7 days tailor-made from £2,300 per person View trip
Los Angeles And Palm Springs
Tailor-made HolidayCombining Los Angeles with Palm Springs makes for the perfect twin-centre Californian itinerary. Los Angeles has many names: LA, the City Of Angels, and Tinseltown. It's the home of Hollywood; it's big, brash, plastic fantastic, and strangely outrageous. Somerset Maugham called it "A sunny place for shady people." Some of the LA stereotypes hold true but it's very much a city of surprises. It's also one of the most gay-friendly cities on earth.
8 days tailor-made from £2,225 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.