Anguilla XV, or There and Back Again

Spoilers: the view from Roy's studio in Sandy Ground

While I’ve dreamed of spending part of the winter holiday season in Anguilla ever since my first taste of the island back in 2009, I never really thought it would be a reality, thanks to the fact that I’ve been the manager of an independent bookstore for most of the last two decades: time off in December is as rare as hen’s teeth when you work retail. That all changed for me about 18 months ago, when I got my dream job and in a topsy-turvy change of fate, suddenly had more downtime in December than I’ve had since I graduated from college.

Still, I didn’t think a trip to Anguilla during Festive Season would happen any time soon since 2023 was the Year We Bought Our First Home, and while my husband’s and my coffers weren’t entirely depleted, we also had to contend with replacing our entire heating system for our first winter season. We knew that we’d want some sort of small vacation to mark a Big Year with Lots of Changes, so I diligently searched where we could go using my cache of airline miles. I’ve always wanted to see the Christmas markets in a major European capital, and we very nearly went in that direction for variety of reasons: miles could get us there, we have friends who just moved from the US to Edinburgh, and we’ve been longing to return to the UK after falling in love with London in 2019. There were just two catches: with six days of vacation to play with, we didn’t want to lose 1/6 of our trip to jetlag AND my husband’s job had taken a pretty stressful turn in the fall, so we decided that a more relaxing trip was the wiser option.

Taking no chances on getting sick and ruining the trip!

Since I’m never going to fight too hard against planning a relaxing vacation in a tropical locale during the winter months, that was all A-okay with me. I checked all the places Delta flies but was having trouble finding two tickets anywhere in Mexico or the Caribbean using my FF miles. I could get one FF ticket but then would have to pay $800-1200 for the companion fare, depending on the destination. Feeling a little down in the dumps, I did what I sometimes do when I’m procrastinating, or feeling restless, or it’s a Tuesday: I checked flight prices to Anguilla on all airlines, not just Delta. First I checked prices into St Maarten, on the off chance that I might see something affordable, but nothing did I spy. Figuring I had nothing to lose, I checked prices for flights right into AXA. LO AND BEHOLD, there was one American Airlines flight that showed up for significantly less money than I’ve ever paid to fly to either AXA or SXM. In fact, the price was so low that I could book two of us for less money booking a single fare on Delta to many of the other destinations we had considered.

Sunrise from the plane

My heartbeat raced. Could it be? Could we possibly be lucky enough to find ourselves in my favorite spot on earth for New Year’s Eve? A quick glance on the VRBO and AirBnB apps showed no shortage of accommodations in our price range (a mere $150/night), so with the airtight logic that while this was still more than we wanted to spend for this particular trip for the reasons stated above, my husband solemnly pronounced that we would never be able to get to Anguilla for less money, ever, and so we should go with that.

I’m not sure I’ve ever been happier to purchase two plane tickets. I booked a rental car with Ronnie Bryan immediately thereafter and then began one of my favorite tasks: finding a place to stay that fit our budget and our few accommodation requirements: optional a/c in the bedroom, a central-to-west location, wifi, and a kitchenette. My biggest nice-to-have for this trip was a view or walking distance to the beach, but truly never thought we could find that, given that our budget would have been tight even for low season travel, much less Festive Season.

It always feels lucky to spy a rainbow from the plane

Enter: the studio above Roy’s restaurant. I’d heard of it before, of course, but there aren’t many reviews on line that I could find, so I took to the forums to find somebody who’d stayed there before and messaged them directly. Carolee gave me the personal experience and assurance that I’d hoped for and I booked online. Patrick and Claire, the hosts, were helpful and communicative at every step of the process, including when I wanted to frontload one more night to our trip. I’ve always read that Anguilla doesn’t have to be an expensive destination, despite its reputation, and so for my 15^th visit to the island, I was about to find out if that was true.

Outdoor seating area at the apartment

Thus it was that  at 3:30am on 30 December, we found ourselves scraping the ice off our car and making a pre-dawn drive to the airport for our flight to Miami. To sum up, our MIA flight was turbulence-ridden and significantly delayed, so we were doubly glad that we'd booked the longer connection there (the idea being we'd try to get standby on the earlier flight if we arrived in time). We used the extra time to take a walk through the concourse, eat breakfast, and do a little people watching. The MIA-AXA leg was delayed but uneventful and it felt marvelous to land in Anguilla and see how green the island looked. Immigration was quick and easy, as was locating Ronnie Bryan's rental car in the parking lot. 

Inside the studio

We made one quick stop at Syd & Pete's market for bottled water and half & half (we always travel with our own coffee and didn't need anything else for our first morning) before heading down the familiar hill into Sandy Ground to arrive at our new home for the week. Wayne greeted us and showed us upstairs to the studio apartment, which was light and airy and inside, where we promptly dumped our bags to change into some weather appropriate clothing and then hurried downstairs to Roy's to have a quick sunset drink at the bar before walking up to the beach for our dinner reservation.

That string of colored lights guided us home every night

This was a pretty long preamble, and it only covered the pre-trip and arrival! I promise that the rest of my trip updates will be more photo forward and less loquacious. Stay tuned for dinner up the beach at SandBar and the rest of our pinch-me-how-did-we-manage-to-pull-this-off trip.