Anguilla Travel Guide

Anguilla Travel Guide FlagAnguilla is the northern most island of the Leeward Islands in the Caribbean. In total contrast to the rest of the Caribbean, Anguilla is a low laying coral island. It is 35 square miles in area with a population of around 15,000. The name comes from the Spanish word anguila meaning “eel”.

Anguilla travel guideThe island was first settled by Native Americans from Venezuela around 1300BC. English settlers came from nearby St Kitts in 1650 marking the first European colonization of the island. For the most part, Anguilla has stayed in British hand from then until now. Starting in 1825 the island was administered by St Kitts along with Nevis and in 1967 the process began to have all three form an independent country. Well no one asked the Anguillan what they wanted, because they most definitely did not want to be with St Kitts & Nevis. About 20 of them sailed over to St Kitts in local fishing boats and attacked the police station. No one was hurt, but everyone was scared of the “crazy” people on Anguilla and the British government allowed them to stay as an overseas territory while the other two islands formed a country.

Anguilla Travel Guide - Sombrero Island

Sombrero Island

On a side note, Sombrero Island is an uninhabited island administered by Anguilla and laying 35 miles to the north. This aircraft carrier looking island is an out of the way rock that is roughly a mile long and a quarter of a mile wide. In the latter half of the 1850’s illegal American guano miners (for fertilizer) were run off the island by the British who continued the operation until around 1890. The first of three lighthouses was built in 1868. Today, the island is basically a bird colony with old equipment rusting away while an automated lighthouse keeps guard.

My Visit

In the spring of 2017 I sailed the Guiding Light on a six-week cruise in the upper Caribbean. I had the perfect weather to do it, so the first stop was at Sombrero Island. Towards the end of the cruise I swung Guiding Light towards St Martin, but ended up going to Anguilla on a whim instead. We spend a couple glorious days here before heading back to the Virgin Islands.

Likes, Dislikes, and Recommendations

Anguilla travel guide - Little Bay

Little Bay, which you have to get to with a boat or climb down the cliff

Anguilla is a wonderful island with 33 different beaches. The people are unbelievably friendly and it is a wonderful place to visit. I recommend spending a day in a rented car driving the island and exploring the different beaches. While there are some historical places, they are not abundant.

Anguilla travel guide - Sandy Island

Sandy Island

If you keep your boat in Road Bay, visiting is essentially free, but in order to sail to any of the other bays or islands you have to get a rather expensive cruising permit ($56 a day for my boat). With that said, it is worth sailing to several of the bays (Little Bay was our favorite) and Sandy Island (w/ a bar), Prickly Pear Cays (w/ 2 bars), and Dog Island (deserted) are a blast to visit.

Below you can get even more helpful hints by watching the travel video I made for Anguilla and Sombrero Islands. Also, you can read what all I did there in my blog posts located below the video.

All Blogs From Anguilla