It may be summer in New York, but it’s not too early to start planning winter travel. The Caribbean is always appealing and Anguilla is particularly striking. The British West Indian Island just north of St. Maarten and St. Barts has long enjoyed unfair advantages over its Caribbean neighbors. With over thirty gorgeous white sand beaches on just a sixteen-mile-long island, Anguilla has consistently won the “Best Beaches in the Caribbean” title from travel press and visitors. The island remains a true West Indian charmer: reggae sounds, tropical breezes, great Caribbean cuisine, and an abundance of activities make Anguilla a top destination to kick back, enjoy, and play.
It is no surprise that this island is so pristine. In 1980, the government of the virtually hotel-free island decided to limit development to discreet, small hotels and elegant, upscale resorts.
Thirty plus years later, the island has stuck to this policy; this means there are no casinos, large cruise ships, or shopping malls. Large-scale hotel developments have been limited as well. While many Caribbean islands have been over-commercialized, Anguilla continues to retain its local Caribbean charm.
Nevertheless, the comforts of luxury properties are surely available. High-end villas have become the de-facto choice of residence for visitors. These properties are unique and private—spanning thousands of square feet and offering amenities such as gourmet kitchens, full gyms, infinity pools, and butler/concierge services. These villas average about $1,ooo a night and up, depending on the time of year. The Grand Outlook Castle and the Villa Nirvana truly epitomize such mega-villas.
The Grand Outlook castle has 4 bedrooms and 4.5 baths: accommodating up to 10 guests. Built in 2007 on the second highest point on the island, the views are spectacular, with St. Barts, St. Maarten, and St. Kitts visible from its high perch. While very secluded, the villa is a just short drive to many of the island’s attractions, including many of beautiful beaches of Anguilla. Directly below the villa is Little Bay Beach, a tiny beach known for some of the best snorkeling on the island. You can hike down to beach from the villa, or jump on a quick water taxi from neighboring Crocus Bay Beach.
If you’re not feeling adventurous, the infinity pool at the castle is the place to be. The illusion of pool meeting ocean is truly a delight, but unlike other infinity pools, the view here is unrivalled. For creature comforts, the villa is also stunning, starting with an expansive gourmet kitchen that is perfect for novices and chefs alike to work their culinary magic.
The living spaces both inside and outside the house offer ample comfort, space, and luxury. All bedrooms are master suites, with expansive master baths and private balconies—ensuring the luxury of space to each guest.
A dedicated concierge service and daily housekeeping attend to the needs of all guests. The concierge can schedule transportation, make restaurant reservations, or even arrange for a masseuse or private chef.
The owners of the Grand Outlook Castle, Elise and Paul Alegria, together with their friends Sandy and Scott Comstock, have spared no expense to make this one of the grandest properties on Anguilla and the Caribbean.
Villa Nirvana is a relatively new 4-bedroom property boasting its own magnificent views. It overlooks the Caribbean on one side and the beach village of Sandy Ground on the other.
Sandy Ground is arguably the hub of dining and entertainment of the entire island, with several restaurants and bars on just a short stretch of beach. Besides the famed Elvis Bar and the Pumphouse, there are several fine dining establishments: the lauded Veya, romantic Sandbar, and bustling Dolce Vita.
However, if you choose to spend more time in the villa, it is a gem– especially perfect for families with kids and others in tow. The house has a full floor master suite on the top floor for mom and dad, featuring multiple balconies, outdoor shower, and hot tub, while there are two bedrooms on the first floor for the kiddies, and a separate en suite bedroom on the lower level for grandparents or the nanny.
The main floor has a spacious living/dining/kitchen area, which flows nicely into the infinity pool and dining deck. You can keep your beach bod in tiptop shape at the in-house gym. And, as with the Grand Outlook Castle, there is both concierge service as well as daily housekeeping.
Both the Grand Outlook Castle and Villa Nirvana set impossibly high standards in regards to comfort, amenities, and views for all other villas on the island. Enjoy the privacy and true luxury that these estates have to offer and when you venture out into the island, make sure to feast on some freshly caught fish, sip a ‘Dark and Stormy’, and take in the live reggae and jazz music. •
Grand Outlook Castle
Old Outlook Hill, Anguilla, BWI
Shannon Hill, Anguilla, BWI