The island of Anguilla, a somewhat less-traveled-to paradise, has continued to cement itself as a favorite destination of Tradewind guests. Tradewind’s scheduled service to the island is offered from December through April, providing the most seamless way for travelers to reach this little slice of paradise.
Anguilla scheduled flights depart from San Juan and offer a one-of-a-kind onboard experience, flown by modern Pilatus PC-12 aircraft. Guests can opt to purchase Tradewind’s VIP Experience, which offers a convenient transfer between flights. A Tradewind representative will meet guests at their arrival gate, escort them to the private Tradewind lounge, and retrieve their luggage, all while guests sit back and relax to enjoy the complimentary snacks and refreshments available in the lounge.
In addition to flights being available on Tradewind’s website and all major ticketing systems, they also have interline agreements with American Airlines, United Airlines, and JetBlue Airways, allowing single-ticketing and a smooth transfer to Anguilla, in addition to automatic luggage transfer.
Once you arrive on the island of Anguilla, there are scores of top-tier accommodations to choose from. The best hotels in Anguilla combine luxury with a laid-back, toes-in-the-sand vibe, while villas offer seclusion and privacy.
Read on to learn about the best accommodations in Anguilla, many of which offer Tradewind guests exclusive perks.
Cap Juluca, a Belmond Hotel
This luxury property is located on arguably the best beach on Anguilla, Maundays Bay. This half-moon beach on the western end of the island offers crystal clear, calm waters ideal for snorkeling. Cap Juluca is one of the island’s gems, where Belmond’s signature warm service shines, and Tradewind guests can take advantage of an exclusive offer during their stay. The hotel offers fine dining options, as well as one of the island’s best infinity pools.

Malliouhana
This five-star property on the north side of the island has long been a favorite among Tradewind guests—and other visitors to Anguilla. Malliouhana opened in 1984 as one of the island’s finest new resorts, and this year marks its 40th anniversary. To celebrate, the hotel is reimagining its extensive wine collection, rolling out new menus at all its on-site dining outlets, showcasing a boat-inspired art collection, and hosting special events throughout the year. The resort promises its festive season offerings will be better than ever this year—providing an ideal reason to plan a visit in December.

Zemi Beach House
Located directly on Shoal Bay, Zemi Beach House feels like an upscale beach home that happens to be an exquisite boutique hotel, which also offers an exclusive offer to Tradewind guests. A highlight of the property is its spa, which is set in a 300-year-old Thai house that was imported and painstakingly restored into house treatment rooms. Zemi Beach House is located on the northeast side of the island, just steps from Shoal Bay Beach — and although the property’s dining options are excellent, it’s worth planning to venture to one of the authentic Caribbean restaurants that line the beach for a toes-in-the-sand meal as well.

Altamer Luxury Villas
For those traveling with children or a larger group, a private villa can be the most comfortable option. In Anguilla, one of the finest choices is Altamer, which combines the comfort of a private villa with the amenities of a 5-star resort. Villas at Altamer come with personal butler service, which means you’ll have someone who knows the island like the back of their hand arranging whatever you need – whether a private chef, live entertainment, private boat charters, sailing lessons, or more.
Travelers who journey to Anguilla with Tradewind and stay at Altamer’s Blue Diamond or Antilles Pearl villas have exclusive access to an exclusive offer package.

Nevaeh Villa Anguilla
This luxury villa rental offers true privacy to guests who value spending time with friends and family in a secluded paradise. The Balinese-inspired nine-bedroom estate sits directly on Long Bay, a half-mile stretch of pristine sand and clear blue waters. The property sits on more than an acre of beachfront, which means your exclusive retreat is exceedingly serene. But the villa is anything but boring—when you need a break from the island sun, there is the opportunity to play tennis or basketball or utilize the property’s golf simulator, private gym, and home movie theater. Booking a stay at Nevaeh means you also have access to the property’s staff, who are on hand to assist with anything you might need, from coordinating candlelit dinners on the beach to private yoga sessions, and Tradewind travelers can take advantage of a special partnership offer.

Anguilla remains a hidden gem in the Caribbean; however, more travelers are beginning to discover its beauty as a relaxing paradise to visit year after year. There’s no time like the present to plan your upcoming winter getaway and experience all it has to offer, and the Tradewind team would be happy to assist in getting you there with ease.
To learn more about Tradewind’s private charter and scheduled flights to Anguilla and booking your vacation, please visit our website. To receive a private charter quote, please submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-800-376-7922 option 2. For questions regarding scheduled flights, contact our scheduled service team at scheduledservice@flytradewind.com or 1-800-376-7922 option 1.