Tripnotes: Long Weekend in Anguilla

Some trips you plan leisurely with time to spare, and others...well, let’s just say, this trip came together completely about 2 days before our scheduled departure to San Juan. I won’t bore you with the details of how and why, but as luck would have it, everything fell into place and I was finally able to get EXCITED about traveling to Anguilla.

We had booked flights to San Juan, spending an evening there and then hopping a puddle jumper to Anguilla the following morning. I wished we had more time to explore Old San Juan (a favorite of mine since I was a little girl), but we literally landed so late our only food option was room service. Not my ideal evening in Puerto Rico, but it would have to do.

After a quick dip at the hotel pool, it was off to the airport. I have to say flying to Anguilla is not recommended for the faint of heart...if cramming yourself into a 9 seater turbo prop plane with no air conditioning or liquid refreshment doesn’t appeal, you might not want to read any further. For real. One of 9 seats is shot-gun next to the pilot. I consider myself pretty adventurous, but there were some armrest clenching moments where I thought “I hope my my Mom never finds out about this...”.

A white-knuckled hour or so later and we were safely on the ground at the very rustic Anguilla airport. After all that high flying, I was ready for a drink, and lucky for me, there was one with my name on it at The Viceroy.

Checking in to the Viceroy Anguilla is like warm cookies and milk. The lobby is low-key and glamorous all at once. We learned upon check-in that we had been upgraded to a lovely Villa complete with a “Lifestyle Coordinator”, aka butler. I mean, that’s normal life, right?

Our villa was too perfect; An infinity pool overlooking the ocean, enormous spa-like outdoor showers and cushy bedrooms, all designed perfectly thanks to the Miss Kelly Wearstler.

My favorite had to be the chef’s kitchen, described by our “Lifestyle Coordinator” as “a standard kitchen”. We made use of this on multiple occasions, including one night where we grilled beautiful fresh Anguillian Lobsters.

Truth be told, this Tripnotes is more visual than most since it was pretty much impossible to leave the Villa/Resort. There was some loose talk of snorkeling and boat trips, but once we checked in all of those ideas quickly disappeared. Nobody wanted to leave.

The one place we could agree on visiting off campus was Blanchard’s Beach Shack. While the food at the resort was tasty, the price tag was slightly off putting. Blanchard’s was a 5 minute walk down the beach and the food and ambiance was fantastic. Toes firmly planted in sand, we enjoyed jerk chicken sandwiches, fresh cut french fries and Red Stripes. Life was good.

For the most part, we fell in to a lazy routine of lounging by our villa pool all morning, venturing to Blanchard’s for lunch, and then retiring back to the Villa for board games and cocktails.

Evenings we either ate-in or trotted down the beach for dinner (we loved Straw Hat).

Anguilla is known as a foodie island and had tons of restaurants that sounded interesting, but the convenience of our resort made it difficult to justify getting in our rental car to drive 30 minutes away for dinner. I hope that when we go back, we’ll try some out some new places, but if we stay at The Viceroy, the chances of that happening are pretty slim.

All in all, this vacation was probably the most relaxing I’ve ever been on. And, without a trip to the Spa! The resort itself is gorgeous – it basically feels like you’re walking around in an issue of Elle Décor. All. Day. And the people are warm and friendly.

Despite the headache of planning this trip, it could not have been more perfect once we arrived. And I can say without a doubt that we will go back. Thanks for the memories, Anguilla. You’re tops!