One Week in Anguilla Itinerary

Get inspired to visit Anguilla? The unspoiled beaches, white sandy, and ocean breeze can make anyone dash away to this Caribbean escape. I spent a week in Anguilla and felt it was the perfect amount of time to get to know this little hideaway. Here is my one week itinerary in Anguilla:

Day 1:

To get to Anguilla you will have to fly into St. Martin and ferry over to Anguilla. After you check in to your hotel, have a relaxing, little effort afternoon by the pool getting acquainted with the island. After a welcoming afternoon to the Caribbean sunshine, get changed for dinner. An easy and fancy dinner on Day 1 is to do dinner at your hotel with the ocean view.

Day 2:

Today you are refreshed and recovering from the jet lag and ready to explore the island! Head over by the Four Seasons to where Meads Bay is. Here you will find silky white sand and turquoise blue water. Pro tip: pack a cooler and sit away from the Four Seasons so you don’t need to pay $20 a drink! If you are staying at the Four Seasons, they have kayaks, stand up paddle boards, and sailboats you can take our for free!

After a morning on the beach, walk to Blanchard’s which is at the far side of the beach on Meads Bay. It is absolutely delicious and cheap. One frozen drink is only $8 and that was more expensive than the food itself. Beer is even cheaper. The best part, the tables are right in the sand and no shoes are required.

After lunch, go to Byron Bay which is right next door to Meads Bay. Go to the far right side of the Bay for some good snorkeling. Not great, but decent. This is a good celebrity spotting beach as many celebrities are known to have a place right up above this beach. End the day at Straw Hat for dinner and Sunshine Shack for after dinner drinks!

Day 3:

This was my absolute favorite day of the trip, so be ready!! You are going to head over to Sandy Ground where you can take a $10 public “ferry” which is really just a 20ft boat over to Sandy Island. If you go right at 10am when they open, you will literally be the first one on the small island. If you can even call it an island because it’s only a few hundred feet long and wide with one beach shack and some chairs on it. This place is GORGEOUS. This island is the epitome of what Anguilla means to me. Almost exclusivity with live music and fun drinks, white sand, and blue water. The snorkeling right off the island is really good too!

You can have lunch here which has somewhat expensive, but really amazing lobster so I have heard. After lunch take the ferry back and head over to East Shoal Bay which is one of the top beaches on Anguilla. You will find white powdery sand and blue water here as well. This beach is well known for snorkeling. The snorkeling is a bit of a trek so be prepared for a work out. There are restaurants along this beach if you get hungry for an appetizer.

Finally, end the night at Coba for dinner and Elvis Bar for after dinner drinks. Elvis’s has fun music, a great beach atmosphere, and corn hole!

Day 4:

Get ready for an all day sail to Prickly Pear Island! For me, it down-poured on this day of my trip, but it actually ended up to still be one of the best! We stopped at Little Bay which ended up being my favorite snorkel spot. I saw hundreds upon hundreds of fish, an octopus, stingray, and a turtle!! One nice part, there was an open bar from 9am to 4pm so you can saw rum punches all day.

While the rain stopped us from going to Prickly Pear Island and I can’t speak to that, we did stop at a beach with a beach volleyball net and lunch. After lunch we headed over by Sandy Island for another snorkel spot. After the cruise, you will probably need a nap and an easy going dinner and drinks at Sunshine Shack.

Day 5:

Okay I know I’ve said this about every day so far, but another spectacular day lined up ahead of you. If you are scuba certified, use this morning for a 2 tank dive in some of the clearest and warmest waters in the world. If you are not a diver you can do a Discover Scuba class which is basically an introduction to scuba diving without getting certified or you can do another great island activity like horseback riding on the beach or an ATV ride.

The first dive went to 80ft max and the second dive went to 60ft max. Visibility was great, even at the very bottom you could see the top clear as day plus it was warm! I had a shorty wetsuit and many people just wore a rash guard! The entry was a little new for me as it was a seated boat entry where you flip over backwards into the water from the boat.

We did wreck dives which was AMAZING and so unique for me and I think unique to The Caribbean. I swam around large sunken boats with coral growing off the side creating a home for fish, lobster, barracuda, stingray, and turtles. While we had a guide, we just buddied up and swam around at our own leisure and went up when one of us got low on air.

This is going to be a pretty exhausting and early morning so you will be ready for lunch at Elvis Beach Bar. After lunch, spend the afternoon at leisure by the pool at your hotel or the beach by Sandy Ground which is right by the diving.

Get a nice and romantic dinner at Veya tonight. Veya has kind of a jungle feeling.

Day 6:

Your final full day! Insert tear face. Do not fret, I have another great beach for you to end on. Rendezvous Bay is much like the other beaches with pretty white sand and fun beach bars lining the sand. In fact, Dune Preserve is on this stretch of sand and it is the most famous beach bar in the world. Spend the day lazing by the water and drinking Pina Coladas and winning at some corn hole!

Day 7:

You have reached the final day. If you have any time before the ferry ride to St. Martin, catch some last rays by the pool. If you cry, I totally understand. I didn’t want to leave either!!