Tailor-made Vacation · Bermuda
Classic Bermuda Escape
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
Experience 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 flavour of Bermuda’s duality.
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Discover cosmopolitan Hamilton by boat or yacht with its prestigious fine dining scene, alongside the UNESCO-listed charm of St. George’s and the iconic pinks sands of Horseshoe Bay.
Enjoy curated excursions to hidden beaches, sunset cruises over crystal clear waters, and days at leisure in luxury beach resorts where privacy and exclusivity are paramount.
Whether you are cycling the Railway Trail, diving shipwrecks, or sipping Dark ‘n Stormies at a waterfront bar, this is an island escape brimming with variety and island indulgence.
Bermuda is ideal for couples, solo travellers or LGBTQ+ honeymooners seeking sun, sophistication, and a slower pace.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Days 1-3: Arrival, Beach Relaxation & Diving
Arrive in Bermuda and settle into a luxury beachfront resort in Cambridge Beaches on the west coast, set amongst calm waters and pink sands. Spend your first full day unwinding at Horseshoe Bay, one of the most iconic beaches in the world, or opt for a quiet cove along the South Shore Park.
Embark on a curated West End tour exploring the Royal Naval Dockyard where you can learn about the country’s rich naval heritage, discover boutique shops and enjoy rum tastings at the historic Bermuda Rum Cake Company. Dive into the underwater world with a private snorkelling or scuba excursion among coral reefs and shipwrecks teeming with tropical fish.
Return each evening to fine dining overlooking the ocean, with the option for a sunset catamaran cruise on your second night.
Days 4-5: Cultural Hamilton & Culinary Delights
Relocate to a boutique hotel or waterfront property that is just a short ferry or taxi into Hamilton, the island’s capital. Start your day with a walking tour of pastel-fronted buildings, art galleries, and hidden gardens, learning about Bermuda’s British and Caribbean-influenced heritage.
Indulge in a curated food tour featuring fresh-caught wahoo, traditional fish chowder, and locally inspired cocktails. In the evenings, enjoy live music at bars along Front Street and fine dining at waterfront restaurants like 1609 or Blu Restaurant.
Choose between wellness experiences, such as spa treatments with ocean views, or adventure options like jet-skiing around the Great Sound or paddleboarding at sunset. The choice is entirely yours. Bermuda is the ideal location to switch off from the world.
Days 6-7: Railway Trails & Island Adventures
Venture into the island’s lush interior with a guided cycle or e-bike tour along the Bermuda Railway Trail, offering panoramic views and access to secluded coves. Stop for a picnic or swim at hidden gems like Jobson’s Cove or Warwick Long Bay.
The Crystal Caves are a must-visit – an underground world of stunning stalactites and crystal-clear pools. Combine this with a stop at the Swizzle Inn, birthplace of Bermuda’s famous rum swizzle.
Optional activities include cliff jumping at Admiralty House Park, a round of golf on one of Bermuda’s world-class courses, private yoga classes or private perfume making.
Days 8-10: Historic East End & Tranquil Farewell
For your final days, stay in the UNESCO-listed town of St. George’s – a charming enclave of cobbled streets, heritage homes, and centuries-old churches. Explore Fort St. Catherine and the town’s open-air museum-like squares, where history and island life intertwine.
Enjoy a private yacht charter around Castle Harbour or a kayak excursion through the crystal-clear waters of Tobacco Bay. Your final evening includes a farewell dinner with ocean views and local live music that makes for a fitting celebration of your time on the island.
On your final morning, take time for a final beach stroll or swim before your transfer to the airport.
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
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.