A Weekend in Anguilla: Your Perfect Two-Day Itinerary

Written by Kristen Rogers
November 22, 2018

Table of Contents

Last Updated on January 13, 2022 by Boatsetter Team

Anguilla is a bit of a hidden gem as far as Caribbean islands go as it often seems to get forgotten by celebrities, jet-setters, and tourists. Just East of Puerto Rico, the shimmering waters and sandy beaches are prime for exploring. The island is pretty tiny and traveling around can be very simple, especially by boat with Boatsetter. So, if you find yourself with a weekend to kill, consider exploring this often-overlooked Caribbean jewel. Here is your perfect two-day Anguilla itinerary.


Cap Juluca, Anguilla

Cap Juluca, Anguilla

Morning: Breakfast at Le Bon Pain one of the best French bakeries on the island. It is located in Island Harbour and serves freshly baked croissants and freshly brewed coffee. The perfect start to a Caribbean day. Following breakfast, spend the morning hours enjoying a few of the 33 different beaches, all of which are public. Even if there is a hotel built right up to the shoreline, the beach will still have public access.

Afternoon: If you end up on Meads Bay Beach, then you can grab lunch at a place called Blanchard Beach Shack where most of the ingredients are organic. Dine on the coconut curry mussels or the jerk chicken tacos and then finish it off with one of their classic sundaes. After lunch, spend a little time partaking in the water sports the island offers. Paddle down the island’s waterways in a clear bottom kayak or give your abs a workout on a stand-up paddleboard.

Evening: Make your way to North Hill Village at dinner time for the fine dining options at Veya. The menu is full of specialty seafood dishes that you can sample while sitting under the stars on their terrace seating area. If you still aren’t ready to call it a night after your dinner at Veya, grab a drink or two (or three!) at Elvis Beach Bar which was built from a wooden boat. The atmosphere at Elvis can change from day to day; sometimes you might find dancing and sometimes you might find people playing limbo.


Boatsetter Boat Rental- Saint Martin

Boatsetter Boat Rental- Saint Martin

Morning: Start the morning right with a full breakfast from Roy’s Bayside Grill. You can get traditional food like bacon and eggs, or you can opt for something a little more interesting like the lobster eggs benedict. After breakfast, you can check out the Heritage Collection museum in the East End if you are into all thing history and want a better look at the island culture.

Afternoon: Lunch on day two should definitely be all about the local BBQ. There is a place in the valley called The Strip which is where you will find little barbeque shacks and street vendors lined up and ready to serve some of their delicious smelling food. If you are feeling the need for further relaxation after lunchtime, you could opt for a spa treatment at one of the facilities on the island or a relaxing cruise along the waterways! Boatsetter’s fleet near Anguilla is perfect for exploring the island in pure isolation! Added bonus? Island hop around the French Part of Saint Martin, which is about a 20-minute boat ride. There truly is no better way to end your weekend than by enjoying the open water on your very own private boat rental.

Evening: End your day of relaxation by finishing with dinner and cocktails at the Four Seasons.

A weekend spent in Anguilla is the perfect way to experience a Caribbean adventure. It is full of good food, good times, and plenty of sun!

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