North America
Luxury North America Tours
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 Tours 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, travelers 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-center 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 travelers seeking an unforgettable getaway.
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Pacific Coast Drive: San Francisco, Los Angeles and San Diego
Tailor-made VacationDiscover the best of the Pacific Coast Highway on this 14-day road trip through San Francisco, Los Angeles and San Diego. This classic California coastal itinerary combines iconic cities, scenic ocean drives and charming beach towns. Start in San Francisco, home to the Golden Gate Bridge, Alcatraz Island and diverse neighborhoods packed with culture, history and great food.
14 days tailor-made from $6,610 per person View trip
Classic Costa Rica Tour
Tailor-made VacationDiscover a classic journey through Costa Rica, immersing you in untamed rainforests, volcanic landscapes, and pristine beaches. You will experience the vibrant streets of San José, the remote jungles of Tortuguero, the volcanic hot springs of Arenal, the mystical cloudforests of Monteverde, and the sun-drenched shores of Santa Teresa.
13 days tailor-made from $6,745 per person View trip
Ultimate Luxury: Bermuda
Tailor-made VacationThis journey focuses on the best of Bermuda without overcomplicating things. You’ll stay in some of the island’s top hotels, with spacious rooms, strong service and direct access to the beach. Indulge in a number of well-chosen experiences - including time out on the water - give you a chance to see Bermuda properly, without filling every day. Bermuda is one of those destinations where the height of luxury is offered effortlessly.
7 days tailor-made from $10,575 per person View trip
Canadian Eastern Adventure Fly Drive
Tailor-made VacationEmbark on an unforgettable 8-day Canada fly-drive adventure through the captivating provinces of Ontario and Quebec, celebrating the nation's rich English and French heritage. Your journey begins in the vibrant metropolis of Toronto, where you'll immerse yourself in its cultural diversity and iconic landmarks like the CN Tower and Rogers Centre. Next, prepare for awe-inspiring sights as you journey to the majestic Niagara Falls, a natural wonder that promises breathtaking views and thrilling attractions.
8 days tailor-made from $3,310 per person View trip
Luxury Hawaii Adventure
Tailor-made VacationEmbark on an unforgettable Hawaii island-hopping adventure combining the dramatic landscapes of the Big Island with the lush natural beauty of Kauai. Over the course of this journey, you’ll experience two of Hawaii’s most spectacular islands, where volcanic landscapes, tropical rainforests and golden beaches create one of the most diverse destinations in the Pacific. Begin on the Big Island of Hawaii, home to powerful volcanoes, black sand beaches and world-class marine life.
9 days tailor-made from $7,930 per person View trip
Luxury Costa Rica Honeymoon
Tailor-made VacationCelebrate your love with an extraordinary honeymoon in Costa Rica, where untamed beauty meets luxurious seclusion. This journey takes you from the misty cloud forests of Bajos del Toro to the volcanic hot springs of Arenal and the golden beaches of Guanacaste. Every moment is designed for romance, with private candlelit dinners, intimate wildlife encounters, and breathtaking landscapes that set the stage for an unforgettable start to your life together.
9 days tailor-made from $7,870 per person View tripMoments in North America
Bermuda Honeymoon
Tailor-made VacationThis tailor-made escape has been designed for honeymoons, anniversaries and once-in-a-lifetime celebrations and to showcase the very best that Bermuda has to offer. Bermuda is made for romance. Offering soft pink sand beaches, calm turquoise waters and pastel-colored houses, it’s the kind of place where everything slows down, and every moment feels a little more special.
7 days tailor-made from $7,870 per person View trip
Canadian Mountain Highlights
Tailor-made VacationEmbark on an unforgettable journey through the stunning landscapes and vibrant cities of western Canada with this meticulously crafted itinerary. In just seven days, you will have the opportunity to explore the highlights of the region, from the dynamic city of Calgary to the majestic Rocky Mountains and the cosmopolitan streets of Vancouver.
8 days tailor-made from $2,780 per person View trip
Aspen in Winter: A Luxury Gay Ski Escape
Tailor-made VacationAspen is one of those places that rewards arriving with no particular agenda. It's one of the top luxury travel destinations in the USA. The skiing across four mountains is as good as anywhere in North America, but the town itself pulls equally hard: the restaurants are exceptional, the hotels are world-class, and the cultural life punches well above what you would expect from a mountain resort of this size.
8 days tailor-made from $10,445 per person View trip
Ultimate Luxury: Costa Rica
Tailor-made VacationFrom lush jungles to the pristine coastline and cloudforests, this exclusive Costa Rican adventure is designed for those who seek the extraordinary. Over the course of this journey, you will immerse yourself in the country’s vibrant landscapes, encounter exotic wildlife, and experience the ultimate in eco-luxury. Your luxurious adventure begins at Finca Rosa Blanca, a boutique coffee estate where you can unwind amid rolling plantations and sip freshly brewed coffee with sweeping valley views.
From $13,085 per person View trip
Classic Bermuda Escape
Tailor-made VacationExperience Bermuda's enduring charm with our Classic Bermuda Escape, handcrafted to showcase the very best of this North Atlantic archipelago. Along the way, you will discover all of the features that make this nation so unique - pastel-hued houses, hidden coves, and British cultural traditions. Your journey unfolds across the island’s west and east ends, giving you a full flavor of Bermuda’s duality.
10 days tailor-made from $10,575 per person View trip
Canadian West Coast Adventure
Tailor-made VacationDiscover the serene allure of British Columbia’s Sunshine Coast and Vancouver Island with our meticulously crafted Canada itinerary tailored for the adventurous and independent traveler. Immerse yourself in the untouched wilderness of remote resorts, where rugged shorelines beckon with their untouched beauty, offering glimpses of native birds, playful seals, and captivating marine mammals. Embark on guided kayaking tours, navigating the tranquil waters that mirror the surrounding ancient forests.
15 days tailor-made from $2,315 per person View tripGay Group Trips in North America
Set departures with dates already fixed, organized end to end and traveling 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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The Best Places to Visit in June
When it comes to planning a luxury trip, every detail must come together to create a truly unforgettable experience. Whilst we’re experts in crafting bespoke trips around the world, unfortunately, we can’t control the weather or regional events. Read on to discover the best places to visit in June. Canada Though a frozen, snow-covered landscape throughout winter, as summer approaches, locals in Quebec finally begin to lose the thermals.
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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 traveling 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 inquiry to homecoming. No call center, and nothing is charged until you decide to book.