Now that the summer is ending, it’s time to start thinking about holiday travel plans. As a travel advisor, I often get asked about where to go during this time. If you’re dreaming of white sand beaches, turquoise waters, and a slower pace, Anguilla should be at the top of your list. This small but spectacular island in the Eastern Caribbean is known for its pristine coastline, luxurious accommodations, and laid-back charm. It’s the kind of place where you can spend your days barefoot and sun-kissed, yet still enjoy world-class dining and amenities.
Why Visit Anguilla
Anguilla is a British Overseas Territory just a short ferry ride from St. Maarten, yet it feels worlds away from the bustle of larger islands. With more than 30 beaches to choose from, you’ll never find yourself fighting for space. The island’s gentle pace and welcoming locals make it an ideal spot to truly unwind. December through April offers the best weather, with plenty of sunshine and warm breezes - perfect for a holiday escape.
Things to Do
While the beaches are the main attraction, Anguilla offers a variety of experiences to fill your days.
- Beach hop: From the postcard-perfect Shoal Bay East to the tranquil waters of Maundays Bay, each beach has its own personality.
- Sail to Sandy Island: Just a short boat ride away, this tiny island offers soft sand, crystal-clear water, and a beach bar serving up grilled lobster. This island is only accessible by boat.
- Explore the art scene: Visit the Savannah Gallery or Cheddie’s Carving Studio for local art and unique souvenirs.
- Go snorkeling or diving: The island is surrounded by coral reefs teeming with tropical fish and sea turtles.
- Enjoy live music: Anguilla is famous for its reggae and soca beats—head to a local beach bar in the evening for dancing under the stars.
Where to Stay
Anguilla offers a mix of luxury resorts, boutique hotels, and private villas, many right on the beach.
- Belmond Cap Juluca: This iconic property on Maundays Bay is the definition of barefoot luxury, with whitewashed Moorish-style buildings and unmatched service.
- Four Seasons Resort and Residences: Located on Barnes Bay, it offers spacious suites, multiple dining options, and stunning sunset views.
- Frangipani Beach Resort: A smaller, family-owned boutique property on Meads Bay, perfect for those who want a more intimate atmosphere.
Where to Eat
The dining scene in Anguilla is one of the best in the Caribbean, with everything from casual beach bars to fine dining restaurants.
- Blanchard’s Restaurant: A beloved spot in Meads Bay offering creative Caribbean-inspired cuisine in a lush garden setting.
- Sunshine Shack: Located on Rendezvous Bay, this colorful beach bar serves jerk chicken, rum punch, and ocean views.
- Veya: Known as “the treehouse” restaurant, Veya offers a romantic setting and globally inspired dishes with a Caribbean twist.
- Straw Hat: A beachfront favorite serving fresh seafood and cocktails, ideal for a laid-back lunch or dinner.
Anguilla is the kind of destination where the days melt together in the best possible way. You’ll spend your time moving between the beach, the water, and the table, always with the sound of the waves nearby. For a holiday getaway that blends relaxation, luxury, and authentic island charm, this tiny gem delivers in every way.
Ashley Casorio is a travel advisor with a passion for discovering new destinations and hidden gems. She spends her time exploring the world through her job, seeking out unforgettable experiences to share with others.
