My Week In Anguilla | A Step By Step Itinerary.

week in anguilla

I have gone to Anguilla many times and each time I go I want to soak in as much of the island as I can. People that keep on going to Anguilla have a unique camaraderie, I have therefore compiled a schedule based on my many trips of the best week to be had in Anguilla.

Where to stay?

The best value for money place to stay is the Fountain Shoal Bay. It gives quick and easy access to Shoal Bay and many other great Anguilla attractions. The accommodation is very spacious and comfortable but still very affordable. Spectacular views and incredibly friendly service is what the Fountain Shoal Bay has become renowned for. Highly recommend it.

Fountain anguilla residences balcony

Day 1- Sunday

There is a lot of thought in arriving in Anguilla on Sunday. Weekends in Anguilla are a special occasion and you want to sandwich your trip between a Sunday and a Saturday. Fly into St. Maarten and take one of the many boat services from St. Maarten to Anguilla. When you book at the Fountain, they always have great advice on these kinds of travel arrangements.

Once you have checked in head straight to Shoal Bay East. Don’t get caught up in the incredible Shoal Bay Beaches because you will have plenty of time for that. Get straight to Gwen’s Bar. Gwen’s is an amazing Anguilla landmark. The music on Sunday at Gwen’s is a great way to welcome you to the calypso island-style of Anguilla. The food and drinks are fantastic too.

gwensreggae bar image anguilla

Day 2- Monday

Anguilla is all about relaxation, great food and great vibes. Head to Mead’s Bay. Mead’s Bay is one of the best of Anguilla’s numerous incredible beaches. I personally love to sink my toes in the sand in the picturesque beach chairs while enjoying great food and drinks from Blanchard’s Beach Shack. Let the sound of the calm waters soothe you as you sip on a great island mix.

Relax at Mead’s Bay till every sinew and muscle is at optimal tranquility and then head to Mango’s for dinner. The seafood at Mango’s is incredible and the relaxing atmosphere in the open-air restaurant is fine dining and island style at their absolute best.

blanchards beach shack anguilla

Day 3- Tuesday

You need to spend an entire day on Shoal Bay. I always begin the trip with a taste of Shoal Bay at Gwen’s. Then I give it the proper respect it deserves by spending a whole day there on the third day of my trips. Get there early to ensure you get yourself a chair at Medeariman’s. Shoal Bay is my personal paradise. It is a treasure. The tranquil turquoise blue waters and powdery white sand seem to stretch endlessly. Take a walk, have a swim, order food from Medeariman’s, read a book, relax and repeat. It is that sequence that makes Shoal Bay my favorite Anguilla spot ever.

madearimans anguilla

Day 4- Wednesday

Every time I go to Anguilla, I always have that little inner child that feels like I am Robinson Crusoe discovering the island. There is no better way to get your Robinson Crusoe fix than by traveling to Scilly Cay. Scilly Cay is a small island outlet close to the shores of Anguilla. It is far enough to make you feel like an adventurer but close enough to make it easy to access.  The island is untouched. The very natural restaurant and bar on the island serves up great food and drinks for you to enjoy.

scilly cay anguilla

Day 5- Thursday

I always make my 5th day my option and active day. Not overly active but relaxingly active.  There are some things that are not negotiable and are not options though even on this day. It is one thing. That is that I must be at Da’Vida’s for lunch. Da’Vida’s is located on Crocus Bay and is the island benchmark for great food and drinks on the seashore. Dine with your feet in the sand or at a table at the beautiful restaurant. Da’Vida’s usually has great island music and is not negotiable. You must go to Da’Vida’s.

friendly service at Da'Vida Bayside anguilla

Once you are at Crocus Bay, you have a lot of options. If you are a real go-getter you can get around to doing everything. Here are some things that I like to do. Take a dinghy out and snorkel over at Little Bay. You can mix it up and rent sea kayaks or paddle boards. The water is so calm and the reefs are so gorgeous that even the active stuff is very relaxing.

For dinner go over to Artisan’s Neapolitan Pizza, where they make real brick oven pizza and Italian dishes. They of course add island flair and flavor to their dishes and the versatile setting could be romantic or just easy-going.

Day 6-Friday

The highlight of my Friday’s in Anguilla is always dinner at Veya’s. There is a lot to do in between though. I like to go to Sandy Island for lunch and spend the rest of the afternoon reflecting and taking in as much of Anguilla as I can. Don’t eat too much though, because you want to have an appetite for Veya’s.

Veya’s is high-end dining, Anguilla style at its very best. The menu is an eclectic mix of the finest ingredients put together by the Veya master chef. If you are feeling like you need to get as much of Veya as you can then order the Chef’s sampling entrée. It is a delightful mix of incredible dishes. The wine list is also very impressive and ensure that you ask the chef to get a wine that compliments your dish. It never fails.

veya restaurant anguilla

Day 7-Saturday

My last day in Anguilla always starts the same, with breakfast at Geraud’s. If time allows, I always think of my favorite spot and go there one more time. The island is small and the Fountain is well situated to usually allow for it. It is then a sad but see you again farewell to Anguilla.