Tailor-made Vacation · The Caribbean
Barbados & Antigua: Caribbean Jewels
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At a glance
Twelve days across two islands built on completely different relationships with the sea: Antigua's three hundred and sixty-five beaches and Barbados's working coastline of fishing towns and surf breaks.
Antigua opens the trip with five nights, and the island's maritime history is impossible to avoid: Nelson's Dockyard still functions as a working marina, and the hills above English Harbour are dotted with forts built to watch for exactly the kind of ships now moored below them for pleasure rather than defense.
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A day trip crosses to Barbuda, Antigua's quieter neighbor, for a stretch of pink-sand coastline with almost nothing built on it and a colony of frigate birds nesting a short boat ride from shore.
Barbados takes the remaining five nights, and the island reads differently from the moment you land; Bridgetown's UNESCO-listed garrison and colonial streets give way to Bathsheba's Atlantic-facing surf coast on the east, then to Oistins's Friday fish fry and St. Nicholas Abbey's centuries-old rum distillery further north.
Where Antigua is defined by its beaches, Barbados is defined by what happens just behind them.
Both stops have been chosen with LGBTQ+ travelers in mind; Antigua and Barbados are known for their general openness toward visitors, and every property on this Caribbean route has earned its place by demonstrating this.
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.
Day 1: Welcome to Antigua
Land in Antigua and transfer to the island’s southern coast, where the Inn at English Harbour occupies a quiet cove well away from the cruise-ship crowds that gather closer to St John’s.
Check in, then take the rest of the day at whatever pace suits, the resort’s private beach, the pool, or simply the open-air Terrace Restaurant for an early dinner.
Nothing else is planned today. The trip proper starts tomorrow.
Day 2: English Harbour and Nelson's Dockyard
A morning on foot through English Harbour, ending at Nelson’s Dockyard, one of the few Georgian-era naval dockyards still in working use anywhere in the world. Yachts moor here today where warships once did, and the old boathouses and cordage buildings have been restored rather than replaced.
Lunch is at one of the harborfront restaurants that have grown up around the marina, before an afternoon left free for the beach back at the hotel.
Evenings on Antigua tend toward the quiet; most people are back at their resort well before the island’s small nightlife scene gets going.
Day 3: Antigua's North Coast
A driving tour up the island’s less-visited north coast, taking in Fort Barrington and Fort James, both built to guard the approach to St John’s harbor and both offering views back across the water that the original garrisons would have used for exactly that purpose.
The afternoon turns toward the beach; Antigua’s coastline changes character every few miles, and today’s stretch is quieter than most, worth the extra drive to reach.
Dinner back at the hotel or a short drive into English Harbour for something livelier.
Day 4: A Day on Barbuda
A short flight crosses to Barbuda, Antigua’s sister island, low-lying and largely undeveloped compared to its neighbor. The main draw is the pink-sand beach on the island’s west coast, miles of it with almost no development along the shoreline.
A boat trip through the lagoon reaches the Frigate Bird Sanctuary, one of the largest colonies of the species in the world, with thousands of birds nesting in the mangroves during the breeding season.
Return to Antigua by early evening, in time for dinner back at the hotel.
Day 5: Scenic Shirley Heights
A quieter day by design, mornings are left free for the beach or the pool, since today ends later than most.
Shirley Heights, a former military lookout above English Harbour, is the destination for the evening, timed to catch the sunset over the harbor from the same vantage point once used to watch for approaching ships. On Sundays this becomes something of a local institution, with steel pans and barbecue drawing both visitors and Antiguans alike.
This is the last night in Antigua. Tomorrow moves on to Barbados.
Day 6: Onward to Barbados
A short flight this morning trades Antigua’s beaches for Barbados’s working coastline. There is no need to rush; the flight itself is brief.
The Sandpiper, on Barbados’s west coast, is the base for the remaining five nights, chosen for its position within easy reach of both Bridgetown and the island’s calmer western beaches.
The afternoon is left free to settle in, with dinner at the hotel to close out the first day on the island.
Day 8: The East Coast and Bathsheba
A drive across the island to Bathsheba, on Barbados’s Atlantic-facing east coast, where the water turns rougher and the coastline more dramatic than the calm west side seen so far. This stretch draws surfers from across the Caribbean, and watching from the cliffs above is as much the point as the water itself.
Lunch is at a small local spot overlooking the coast before the return drive back to the hotel.
The evening is free; most people are ready for an early night after a full day on the road.
Day 9: Oistins and Barbadian Cuisine
An easier day, built around food rather than sightseeing. Oistins, on the island’s south coast, is best known for its Friday fish fry, but the fish market and surrounding stalls are worth a visit any day of the week.
The national dish, cou cou and flying fish, makes an appearance today, along with rum-based cocktails that are as much a part of the meal as the food itself.
The rest of the afternoon is free, for the beach or simply resting up.
Day 10: Rum Trail: Mount Gay and St Nicholas Abbey
A day built around Barbados’s oldest export. A morning tasting at Mount Gay, the world’s oldest rum distillery still in continuous production, followed by a drive north to St. Nicholas Abbey, a working plantation house and distillery dating to the 1650s.
Lunch is on the Abbey’s grounds, with the afternoon left open before a final dinner on the island.
This is the last night on Barbados.
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Aruba and Curacao stand out as particularly welcoming islands for the LGBTQ+ community, offering a blend of stunning beaches, inclusive resorts, and a warm, open-minded atmosphere.
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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.
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