Tailor-made Holiday · The Caribbean
Luxury Anguilla 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
Anguilla is one of the most exclusive destinations in the Caribbean. It's a small island packed with luxury hotels and world-class beaches. As it's so exclusive, Anguilla attracts far less tourism than some of the bigger islands so it has more of an untouched feel. Over the course of your stay, you’ll explore Anguilla’s local history and art scene, relax at top spa retreats, and take in the island’s natural beauty with time on the beach and at sea. An optional day trip to St. Maarten adds a mix of French and Dutch influences, with shopping, dining, and the famous Maho Beach experience before returning to Anguilla.
Anguilla is home to some of the most exclusive resorts in the Caribbean, and Cap Juluca, A Belmond Hotel and Four Seasons Resort Anguilla stand out as two of the island’s finest. Cap Juluca is a beachfront retreat set along the beach of Maundays Bay, where whitewashed Moorish-style villas offer direct beach access, private terraces, and direct ocean views. The resort is designed for seclusion and relaxation, with private cabanas, exceptional dining at Pimms, and a world-class spa, all just steps from the Caribbean Sea. In contrast, Four Seasons Anguilla is sophisticated and modern, set on the cliffs between Meads Bay and Barnes Bay, with a mix of elegant oceanfront rooms, private villas, and three infinity pools. Known for its contemporary design and upwardly mobile social scene, Four Seasons Anguilla gives you the full 5-star experience. Luxury and relaxation will shape any trip to Anguilla. It's one of the best places in the Caribbean to unwind in style.
Read more
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 & Luxury Island Experiences
Land at Clayton J. Lloyd International Airport via private charter or a transfer from St. Maarten. A chauffeur will escort you to your five-star resort—perhaps the Four Seasons Resort Anguilla, Malliouhana, or the ultra-exclusive Cap Juluca, A Belmond Hotel. Spend your first afternoon unwinding on the pristine sands of Meads Bay Beach, where private cabanas, cocktails, and impeccable service set the tone for your stay. As the sun begins to set, head to the Sunset Lounge at Four Seasons for pre-dinner drinks before dinner.
Ease into your second day with a morning yoga session on the beach or a rejuvenating treatment at The Spa at Four Seasons. Later, venture to Shoal Bay East, widely considered Anguilla’s most breathtaking beach, where the calm Caribbean waters await. A long lunch at Tropical Sunset ensures you’re well-fed with fresh lobster and rum punch before an afternoon of pure relaxation back at your resort. As the evening sets in, slip into something elegant for a fine dining experience at Veya, a candlelit hideaway serving Caribbean fusion cuisine in a romantic treehouse-style setting.
Day three is all about adventure at a relaxed pace. Board a private luxury yacht for a day of sailing, snorkeling, and island-hopping. First stop: Prickly Pear Cays, a secluded offshore spot where crystal-clear waters and coral reefs offer the perfect snorkeling experience.
Days 4–6: Exploring Anguilla
After breakfast, visit the Heritage Collection Museum, where a private guide will walk you through Anguilla’s past. Continue to Cheddie’s Carving Studio, where local artistry shines through in beautiful handcrafted sculptures. A stop at Rum & Reel for a premium rum-tasting session before heading to Blanchards Beach Shack for a casual gourmet lunch. Spend the afternoon unwinding by your resort’s infinity pool or opt for a private horseback ride along Cove Bay Beach.
Enjoy a spa morning at Zemi Thai House Spa, housed in a restored 300-year-old Thai teak house, where ancient wellness rituals are available. The afternoon is yours to enjoy at Rendezvous Bay, a stretch of soft sand ideal for unwinding in private beachfront cabanas while sipping on signature cocktails from the nearby Sunshine Shack. Come evening, let the romance of the island sweep over you with a private candlelit dinner on the beach, complete with a personal chef.
On the sixth day, set sail on a half-day catamaran excursion, stopping to explore nearby offshore cays and snorkel in hidden lagoons teeming with marine life. As dusk approaches, sip sundowners at The Cap Shack at Cap Juluca, a stylish beachfront bar, before heading to Ember, an open-fire grill restaurant where the island’s freshest seafood and prime cuts are cooked to perfection.
Days 7–9: Private Villas, Hidden Beaches & Departure
Spend the morning at Little Bay, a small cove with breathtaking cliffs, perfect for a peaceful swim. A laid-back lunch at Elvis’ Beach Bar, famous for its fish tacos and rum punch. The afternoon is best spent unwinding at the beach. For dinner, experience Hibernia, an upscale yet intimate restaurant blending Caribbean and Asian cuisine with a great wine selection.
As your time in Anguilla nears its end, let the final full day be one of leisure. Enjoy a long beachfront brunch at Celeste, where fresh tropical fruits, buttery pastries, and Champagne flow.
On departure day, enjoy a final dip in the infinity pool before a seamless private transfer whisks you to the airport. Whether by private charter or a first-class connection through St. Maarten, you’ll leave Anguilla in style.
Further information
Optional Island Hopping Excursion
A day trip from Anguilla to St. Maarten is just a short 20-minute ferry ride or 10-minute private charter flight away. Begin the day in style with a private yacht transfer over the Caribbean waters before docking at the port of Marigot, the chic French capital of the island. Stroll through its streets, stopping at Le Marché, a market filled with local crafts, spices, and fresh produce. Enjoy a gourmet French breakfast at La Croissanterie and try buttery pastries with rich coffee. Continue your journey to the Dutch side, where the cosmopolitan energy of Philipsburg offers designer shopping, beachfront bars, and a chance to experience the legendary Maho Beach, where planes fly overhead as they land at Princess Juliana Airport. For a more exclusive escape, unwind at Anse Marcel Beach, a cove tucked away from the crowds, or enjoy a long lunch at the Michelin-recommended L’Auberge Gourmande, serving refined French-Caribbean cuisine. As the sun begins to set, return to your yacht for a leisurely sail back to Anguilla.
Our Experts
As specialists in navigating the complex Caribbean, we ensure that LGBTQ+ travelers enjoy a safe and unforgettable experience, connecting them with the most welcoming and inclusive destinations in the region.
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.
Stellar 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
Similar tours
Luxury Turks & Caicos Experience
Tailor-made HolidayTwo sides of the Turks and Caicos Islands and one unforgettable week. Vibrant reef-fringed Providenciales followed by the private island seclusion of COMO Parrot Cay. Begin in Providenciales, where Grace Bay's world-famous shoreline sets the scene for your first few days. Whether you're snorkelling the barrier reef, exploring the turquoise stillness of Chalk Sound, or simply claiming your stretch of sand, Provo has a way of filling a week without ever feeling rushed.
8 days tailor-made from £5,100 per person View trip
A Gay Honeymoon in Turks and Caicos
Tailor-made HolidayTurks and Caicos works for a honeymoon because it gets the fundamentals right, from the perfect beaches to the unrivalled luxury hotel offerings. These islands occupy a rare position in the Caribbean: Turks and Caicos is a destination that has managed to attract the world's most discerning travellers without losing the qualities that drew them there in the first place.
7 days tailor-made from £6,380 per person View trip
Four Seasons Yachts
Tailor-made HolidayFour Seasons Yachts operates a 207-metre superyacht carrying 95 suites across 11 decks, delivering hotel-level service in a yacht-sized vessel. The experience mirrors staying at a Four Seasons property that happens to move between ports. Each voyage sails the Mediterranean with overnight stays in marquee harbours and smaller coastal towns that larger cruise ships cannot access.
7 days View tripThe hard part is not finding a beautiful place. It is finding the right one for you.
Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, 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 personalised 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 travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, 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, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
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 personalised 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+ travellers 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 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.