A Luxury Family Vacation in Anguilla

The planning began six months earlier when the COVID-19 vaccines rolled out. We chose Anguilla for its world-class beaches, noteworthy restaurants, and intelligent approach to pandemic containment, one that earned the island a Level 1 classification from the Centers for Disease Control and Prevention, the lowest possible risk level for COVID-19.

We sought a villa big enough to give five adults and two toddlers space together and apart. Along with privacy, we craved a few hotel amenities. Houses at resorts came with crowded beaches, and stand-alone homes lacked services. Long Bay Villas, a cluster of three Mediterranean-style residences overlooking a quiet beach, offered seclusion and staff. We pooled our resources and booked Sand, a 6,500 square-foot stunner with five bedrooms. The three master bedrooms eliminated squabbles over who gets the diva digs, and the toddlers gleefully slept in a cozy bunk-bedded room.

We worked jigsaw puzzles and raced trucks with 4-year-old James and two-year-old Charlotte in the living area, played gin rummy at the dining table, and planned our day while sipping coffee on the deck with its pool, hot tub, and expansive views of the turquoise sea. A concierge assisted us with restaurant reservations and outings, and a housekeeper kept the unit spotless, washing our dirty laundry every day.

Did I mention the butler? Each Long Bay Villa comes with eight hours of daily, complimentary butler service. The management thoughtfully staffed Sand with two butlers in case we needed help with the young kids. Each morning we awakened to complimentary croissants, fruit, juice, and coffee served by Yann and Roberto, who broke out in a wide grin when anyone requested scrambled eggs.

After a long day of travel to Anguilla, we looked forward to a chef-cooked dinner at the property since no one had the energy to go out. The butlers also pre-stocked our fridge, so we didn’t have to race to a grocery store for milk and morning essentials. The butlers served us hors d’oeuvres, followed by a tasty, three-course meal cooked by Chef Marlon. The butlers washed the dishes too. We quickly acclimated to such pampering, splitting our time between exploring the island and savoring the villa.

One morning we swam at Meads Bay, a long swath of sugar-soft sand and calm waters, before lunching at Leon’s, Malliouhana’s beachside eatery. We especially liked the blackened mahi and the crispy sweet potato fries. James and Charlotte munched crispy chicken fingers before taking their first shots at billiards under their dad’s tutelage.

A day outing to Prickly Pear combined two of our family’s favorite things—boat rides and good food. First, we moored at Little Bay, a marine park with a thumbnail of a beach bookended by cliffs. We snorkeled along the rocks, catching sight of lobsters and schools of rainbow-colored fish, and took turns holding James and Charlotte as they giggled and splashed in the sea.

Next, the boat dropped us at Prickly Pear, an uninhabited Anguillan cay with sparkling white sands, chaise lounges, and Prickly Pear Restaurant. Don’t be fooled by its beach shack vibe or the lack of a menu. We sat at the picnic tables and waited. Soon a server appeared with platters of delicious local fare served family-style—grilled mahi-mahi, chicken, BBQ ribs, shrimp, grilled whole lobsters, and crayfish, plus bowls of rice and peas, salad, coleslaw, and sautéed potatoes. We stuffed ourselves, then swam before heading back to the villa for showers and naps (adults too).

One night we timed drinks and dinner at the Four Seasons Resort Anguilla to correspond with the sunset. From the beach and from Salt, the sunsets are spectacular.

Because a recent storm had washed away a portion of Long Bay’s small beach, we hung out at sister property Santosha’s wide sands, a three-minute ride away by butler-driven golf cart. The beach staff provided towels, set up shade umbrellas, and served us cold drinks. Most of the time, we had the beautiful cove to ourselves.

Since James and Charlotte ate dinner early, the butlers picked up food from restaurants for the kids and the adults who stayed with them while the rest of us dined out.

The most important service provided by Long Bay Villas took place before we arrived. At our request and for no extra charge, the property erected a sturdy enclosure around the pool and hot tub that prevented James and Charlotte from entering by themselves. Although someone always watched the kids, the extra safety measure allowed us to relax.

The last night we enjoyed a chef-cooked dinner on a private beach, complete with the aroma of grilled lobster, the crackle of a bonfire as we roasted marshmallows for s’mores. The sky popped with so many stars that the toddlers—and all of us–felt transported to an enchanted setting.