Anguilla Island Tour

Friday marked our last day waking up in Anguilla with friends in town. With the remaining couple’s flight leaving in the afternoon, they had to make their way back to St. Maarten around noon to get everything underway. Boat Shoe Boy and I hopped in the car and headed down to Blowing Point to drop off our counterparts at the ferry terminal. We had spent the majority of our trip soaking up sun and enjoying the festivities of Carnival, but hadn’t explored the island it its entirety much. Granted, Anguilla is a small island (about 13 miles from end to end), but driving from one end to the other seems like an eternity.

Map of Anguilla, Source:

After dropping off our friends, Boat Shoes proposed a little tour of the island. First, we headed to the Valley, the island’s capital, to check out what could best be described as Anguilla’s financial and government center. Legitimate grocery stores dot the area (more like supermarkets and less like the neighborhood corner store), and new government and bank buildings line the streets. From there, we leisurely made our way further to the East End, driving in and out of small communities to get a better feel for local residences.

Shoal Bay East
A fishing village.

The eastern end of the island is home to Shoal Bay East, which is one of the more famous beaches on the island. This end of the island, Boat Shoes explained, was more of a fishing community. Tourism clearly exists — probably due in large part to the pull of Shoal Bay — but fishing is a bit more of a mainstay for locals. There are a few great restaurants for dinner on this side of the island, too, but with the distance between Island Harbour and Meads Bay, lunch seemed a more reasonable option (apparently On Da Rocks, a new restaurant in Island Harbour, is amazing for dinner, though — $5 crayfish on the weekends).

Heading into Gwen's
Lunch at Gwen's!

After taking a stroll on Shoal Bay, we hopped in the car and headed to Gwen’s Reggae Grill for a lunch stop with one of the prettiest views around.  We had stopped into Gwen’s last year and it was one of the places that I remembered with extreme fondness. Hammocks on the beach, wayward palm trees, cerulean waters and a local scratch band that played Caribbean beats to inspired tourists. Lunch on a weekday had a distinctly different vibe, though equally great. We sat on the deck with just a few other patrons: a couple, a father reading to his son, and a few British tourists running around on the rocks and sand abutting the patio.

One of my favorite shots.
So serene.

After a round of fish sandwiches, we headed back to the Frangipani, circumnavigating the street parade that was going on in honor of Carnival. After getting cleaned up, we headed out to a family dinner at Dolce Vita in Sandy Ground. Boat Shoes’ parents mentioned how fantastic the food was at Dolce Vita and I was excited to finally check it out. The vibe was great and after talking with the owner/chef, Abi, for a few moments, we knew dinner was going to be exceptional. If half of the intelligence and passion that this guy had was infused into the food, we would be in great shape. Everything we ordered from start to finish was spectacular. Calamari, caprese salad, gnocchi… yum, yum, and yum. We finished the meal with bananas flambé and a round of Grand Marnier flambé, which proved to be quite the table side show:

Whipping up bananas flambé on the deck.

After our two-plus hour dinner sadly came to an end, we made our way back to the hotel to call it a night, partly due to a glutton-induced food coma, and partly due to being generally tired from sun-laden days. Saturday would mark our last full day in Anguilla, though I tried to put that out of my mind. Check back tomorrow as I recap the trip and post some more photos (of nearly 1000 I snapped) that never made it to the blog.


More about Shannon Kircher

Shannon Kircher is the founder and editor of The Wanderlust Effect. Founded in 2009, she has continued to document her international escapes as an expat in Europe and the Caribbean. Additionally, Shannon is the founder of Compass & Vine, a luxury boutique travel design firm, and is the Director of Marketing for the Frangipani Beach Resort. Shannon holds an MSc in Social Policy and Development from the London School of Economics and is a current candidate for WSET Level 3 in Wines & Spirits.