Anguilla 2024

We scored an amazing last-minute package on Orbitz for Anguilla — flights and hotel included — and couldn’t resist jumping on it. Small but full of character, Anguilla is famous for its powdery white-sand beaches, clear turquoise waters, and a relaxed pace that makes it perfect for a quick getaway. But beyond the beaches, the island has a fascinating history: originally inhabited by the Arawak people, it later became a site of colonial contest between the French and the British, and traces of that history still show up in its culture, cuisine, and architecture.

To make the most of our visit, we rented a car and explored the island at our own pace — and got our first taste of driving on the left side of the road! Highlights included the striking natural formation known as the Arch and plenty of time on Anguilla’s world-renowned beaches. One of the most memorable moments was taking the boys on their very first snorkeling adventure. The underwater world here is vibrant, full of colorful fish and coral — a perfect introduction to the Caribbean seas.

We also made a day trip to St. Martin, just a short ferry ride away. St. Martin is historically fascinating: divided between French and Dutch control since the 17th century, it offers a unique blend of cultures. We toured Fort Louis, built by the French in 1789 to protect Marigot Bay, and explored the surrounding town with its charming streets and markets before heading over to the Dutch side of the island for a quick look.

Back on Anguilla, the island’s warm and welcoming spirit truly shone. While wandering a local grocery store, we ran into a chef buying ingredients for the day. A friendly conversation later, and we were invited to his restaurant for dinner — a highlight of the trip. The food was fresh, flavorful, and perfectly captured the island’s laid-back Caribbean vibe.

Anguilla is more than just a beach destination. Its mix of history, culture, vibrant cuisine, and relaxed charm makes it a place to slow down, explore, and soak up the Caribbean lifestyle. Whether it’s snorkeling with the kids, exploring nearby islands, or enjoying a spontaneous local dinner, Anguilla leaves you already dreaming about your next visit.