Home to some of the most stunning beaches in the world, with over a dozen smaller islands just a boat ride away, Anguilla is a true gem of the Caribbean. It’s a luxurious paradise of soft, white sand, crystal clear water, and miles and miles of natural beauty that sets an idyllic backdrop to the island’s quiet neighborhoods and world-class resorts.
Located in the northern part of the Lesser Antilles about ten miles from St. Martin, this quiet island is a British Overseas Territory, renowned for its sophisticated food scene, live music, and genuine warmth and hospitality. In fact, it’s known as one of the culinary capitals of the Caribbean, boasting over a hundred beloved restaurants ranging from local diners to five-star establishments and playing host to a four-day international epicurean festival each year.
Though the beautiful scenery, great food, and welcoming attitude attracts hundreds of thousands of visitors annually, you won’t find large cruise ships, casinos, or high-rise hotels on Anguilla. Instead, you’ll discover a charming island that’s more low-key and less crowded than some of the other Caribbean vacation destinations, which only adds to its appeal.
A vacation on Anguilla is equal parts adventure, romance, and laid-back, sun-kissed days. It’s a playground of high-end luxury, thrilling outdoor activities, world-class snorkeling, and breathtaking beauty, which may be why it ranks at the top of Travel + Leisure’s Favorite Caribbean Islands list year after year.
Our Anguilla Residence Manager has pulled together her ideal itinerary for three perfect days of fun, sun, and amazing dining on the island and is always happy to help you create your own unforgettable Anguilla vacation.
DAY 1: Beach Time
Start the day with breakfast outdoors on the home’s expansive patio, enjoying the sound of waves meeting shore on the small rocky beach below and miles of blue skies and stunning sea views stretching out before you. Then pack up towels and sunscreen and make the short drive over to beautiful Shoal Bay East beach (12-minutes away) to claim your spot on the soft, white sand.
Considered one of the best beaches in the world, Shoal Bay East is a quiet, postcard-perfect place to spend the day. The turquoise water is calm and clear, a vibrant offshore reef teems with colorful marine life, and the beach’s gorgeous two-mile stretch of sand is dotted in spots with swaying palm trees and low lush greenery, as well as restaurants, resorts, and equipment rental shops.
Best of all, despite its popularity, Shoal Bay East is never overcrowded, avoiding the hustle-and-bustle feel of other tourist-friendly Caribbean beaches and making it the ideal spot for a relaxing morning of swimming, snorkeling, kayaking, or sunbathing. Choose your favorite beachy activities and your Residence Manager will make equipment reservations for you ahead of time.
When you’re ready for lunch, you won’t have to walk far to enjoy a fabulous meal next to the water. We recommend trying the delicious fish tacos, crab cakes, and calamari at the resort-casual Shoal Bay Zemi Beach Club. Or pay a visit to local-favorite Gwen’s Reggae Grill for lobster, shrimp, and chicken hot off the grill, perfectly seasoned sauces and sides, and ice-cold tropical drinks served up in a perfectly laid-back setting.
In the afternoon, cool off with a dip in the pool at your Equity Estates home before heading out for dinner at Straw Hat Restaurant in Mead’s Bay. The half-hour drive will take you through the heart of the island to another of Anguilla’s beautiful beaches, where you will dine on fresh seafood and classic Caribbean dishes with an upscale twist, in a truly gorgeous open-air dining room overlooking the water.
You can’t go wrong with the ceviche starter and seared tuna entrée, though the curried goat, grilled local crayfish, and vegan red curry dumplings are also worth considering, if you’re so inclined. Round out the meal with a fantastic crème brulée or caramelized bananas from the dessert menu. And don’t forget to try one of Straw Hat’s signature rum cocktails or a glass of wine from their extensive bar menu.
After dinner, take an evening stroll along the quiet stretch of beach in front of the restaurant before calling it a night.
DAY 2: Explore on Land or Water
Wake early for coffee by the pool or on the home’s rooftop deck, soaking in the morning sun before heading out for a private, guided hike through the forest and caves of Katouche, located on an 80-acre, locally owned estate on the western side of the island.
Perfect for beginners as well as more experienced hikers, this two-hour trek will take you through a gorgeous valley forest where you’ll learn about Anguilla’s native plants and trees, get a glimpse of local wildlife, and hear interesting stories about the history of the island from your expert guide. From the forest path, you’ll descend into the large open cavern of Cavannagh Cave where you’ll find natural stone archways and rock formations, stalactites, and fruit bats hanging from the 30-foot high ceiling, as well as an impressively tall fig tree that grows up and out through an opening at the top of the cave. The hike ends on the secluded Katouche Bay beach where you’ll refuel in the shade with complimentary Caribbean treats, fresh fruit, and a refreshing cold drink to wrap up your adventure.
After working up an appetite, enjoy a deliciously fresh midday meal prepared by Chef Tyrone in your Equity Estates home, followed by a perfectly lazy afternoon cooling off by the pool. You may also choose to walk down to the private beach below the home and take in the salt air and sea views from a different vantage point, though keep in mind that you’ll need shoes to protect against the rocks and shells, and the water along that part of the bay is too rough for swimming.
That evening, take to the water on a luxurious, private two-hour sunset sail along the beautiful Anguillan coastline, complete with champagne cocktails and freshly made hors d’oeuvres. From the comfort of a classic 50’ foot sailboat, you’ll experience amazing views of the island and the surrounding sea, feel the wind in your hair, and watch as the sun sets gold and orange on the horizon.
Afterwards, grab a late dinner and check out the live music at the ever-popular Elvis’ Beach Bar. Kick off the night with their famous rum punch at the outdoor bar or settle in at one of the seaside tables. The atmosphere is lively, fun, and super casual, and the food (a fusion of Mexican, Caribbean, and classic bar favorites) is unbelievably good. Try the goat nachos if you’re looking for a unique appetizer, and then dig into the peel-and-eat shrimp, house burger, or jumbo wings as your main with a side of sweet potato or cheesy fries for good measure. Elvis’ is open until 1am, so it’s easy to make a full night of it, though you may want to head home early enough to get a good night’s sleep before your next day’s adventures.
DAY 3: Fun, Sun, and Sightseeing
Wrap up your vacation with another day of fun and sun. In the morning, drive over to the lovely Le Bon Pain bakery café in Island Harbour for light, buttery croissants, juice and coffee, and a mouthwatering egg and ham breakfast sandwich served on a fresh-made baguette. The lines can be long at times, but the wait is worth it, especially if you take your meal outside onto the garden patio.
Afterwards, head out to see the sights. Take drive through The Valley, Anguilla’s capital, and admire the historic buildings of the Old Valley neighborhood, including Wallblake House—the island’s only surviving plantation house—and the adjacent St. Gerard Church. Stop to browse through the pieces on display at Savannah Art Gallery. And maybe do a little shopping at Anguilla Bijoux and the colorful Irie Life island gift shop in Sandy Ground.
When it’s time for a bite to eat, grab a seat at one of the outdoor tables at Blanchards Beach Shack on Mead Beach, and feast on grilled Cubanos or jerk chicken sandwiches, cool crisp salads, and their famous Caribbean cornbread. The food and service are excellent, and the views can’t be beat.
That afternoon, take a four-hour private boat charter to two of Anguilla’s best marine parks and snorkel spots—Little Bay and Sandy Island. Enjoy the cruise along Anguilla’s north-west coast on your way out, then stop at Little Bay for swimming, snorkeling, and cliff jumping (for the truly adventurous). Little Bay’s secluded cove is a protected area surrounded by cliffs of layered limestone, with a small soft sand beach and crystal-clear water—perfect for an afternoon swim or snorkel.
From Little Bay, you’ll boat over to Sandy Island, a tiny offshore cay with a lively outdoor beach bar, hammocks, beach chairs, and sugar-soft sand, surrounded by coral reefs teeming with marine life. Look for parrotfish, angelfish, stingrays, and even sea turtles as you snorkel and swim; play a game of volleyball on shore; or simply chill with a cold drink and enjoy the sea breeze and authentic tropical vibe—and views—from the beach or the boat.
That night, we’ll have reservations for you at the upscale Veya Restaurant, one of our favorites on the island. With a creative menu showcasing a fusion of Caribbean, Indian, African, and Southeast Asian flavors, every dish is delicious and exciting. And the look and feel of the restaurant also adds to the experience with a West Indies-style décor, cozy indoor and outdoor dining, and a wrap-around veranda all tucked within a lush, tropical garden.
For the first course, we recommend the grilled skirt steak lettuce wraps or grilled octopus. Follow that with the lemony sautéed snapper or Dijon crusted lamb chops. And end with the decadent key lime pie (in a jar) or fantastic banana cheesecake parfait. If you are a wine drinker, be sure to accompany your meal with a selection from Veya’s extensive wine list (one of the most comprehensive on the island) to round out a truly spectacular dinner.
After eating, settle in downstairs at Meze, Veya’s cozy Moroccan-themed lounge, to enjoy a set or two of live music from some of Anguilla’s best local musicians—a perfect way to end the day and cap off your unforgettable Anguillan vacation.
At Home in Anguilla with Equity Estates
Our stunning four-bedroom Anguilla vacation villa is the embodiment of paradise. Overlooking secluded Lover’s Cove and nestled along a dramatic Anguillan shoreline, this luxuriously spacious residence is truly a tropical retreat. Contemporary interiors in stucco, stone, and rich woods reach out to the expansive patio area, infinity pool, and small private beach. Surrounded by dramatic seascapes and lush landscaping, you’ll savor seamless indoor/outdoor living while enjoying expansive views of St. Martin and St. Barts.
The home’s modern amenities and technology—including a state-of-the art media room, hot tub, and chef-style gourmet kitchen—offer ample opportunities for in-home fun and relaxation after a day out exploring the island. And, with three master suites that open onto the pool area, an upstairs penthouse with its own kitchen and outdoor terrace, and close proximity to some of Anguilla’s best beaches and attractions, this villa is the perfect home-away-from-home for friends’ trips, adult getaways, or family vacations with older kids and teens.
Your personal travel concierge will work with you to plan your itinerary before you arrive and make sure your stay is effortless by arranging reservations for activities, transportation, and dining. Leave the details to us and arrive to a fully stocked kitchen and bar with groceries of your choice from the local market. With Equity Estates, comfort and luxury are yours.
Travel with Equity Estates for a unique and memorable experience. If you would like more information about investing with Equity Estates, please reach out to our Investor Relations team at 404.445.8501 or tap this link to schedule a call. Your incredible Anguilla getaway awaits!
