Back at the beginning of March, Hilton.com had several Carribean and South American properties pricing out at full rate for New Year’s Eve but then at $0 for all nights booked thereafter. It was a glitch, and one that folks at Hilton apparently didn’t realize existed for at least a couple of months. Not long after booking the rates corrected on the Hilton website, with the $0 rates being replaced by the originally-intended full prices.

The deal was flagged for me by a co-worker, and I made the commitment not to share it broadly such as posting it on my blog or on Flyertalk. He was taking the trip for his anniversary and I didn’t want to jeopardize the deal.

Two and a half months after booking the Hilton Barbados (among other possible properties were San Juan and Caracas), I got an email saying there was a mistake and they’d be unable to honor my rate as booked — but that they would extend a single free night (others who booked longer stays got 2 or 3 free night offers).

I e-mailed back a firm but polite note, suggesting that this it was months after I made my Hilton.com booking I should reasonably be able to rely on it. And I had been in e-mail contact with the hotel as well, which suggested my reservation was fully in order. On the phone with the G.M. of the hotel, she subsequently offered me 50% off for the stay. That’s actually not a crazy price, to be sure, but I wasn’t going to make the discretionary trip to take advantage of it.

My New Year’s Eve rate for a King Oceanfront Executive Floor room was $559/night plus tax (it was only incrementally more to confirm an ocean view, and only incrementally more than that for an executive room — but boy New Year’s pricing is expensive there for a standard Hilton!). 50% off would have meant $280/night plus tax, a deal for someone looking to book over New Year’s there, but not enough to fly to Barbados just for the deal.

After some back and forth, the G.M. agreed to honor my originally-booked rate (pay first night at $559, get the rest of the stay free) as long as I consumed the stay outside of their truest peak dates of December 23 through January 6.

The problem was in actually making the booking. This was all arranged by early June, but I kept making every possible attempt to contact the General Manager (a total of at least seven times) — who was the one that agreed to the rate, was the only one who could put it into place for me, and who stopped replying to my messages altogether.

It took getting Hilton corproate involved a couple of times, one of which resulted in the group sales manager contacting me to let me know the G.M. was out of town. But at least at that point I had another person to prompt to get the G.M. back in touch with me.

Finally, my stay with specific dates was booked. Only this wasn’t reflected properly on the Hilton website and I had nothing in writing to reflect the agreed-upon rates. Much more prompting and another phone call from the GM and things were set.

I booked a couple of business class awards on American Airlines. Not the best use of points, perhaps, but pricing over the December period was quite high so an award made some sense and I had no desire whatsoever to make the flight down in coach. Availability really wasn’t bad, though oddly the hardest segment to secure was the outbound flight from DC to New York-JFK, fortunately inventory management opened that up for me so I didn’t have to buy the segment or head up to New York the night before. (On the whole I’ve found American’s award inventory on its own flights to be the best among US carriers, though I find Star Alliance to have better availability than oneworld generally, though I have had quite good luck with British Airways.)

A 6 a.m. departure out of National Airport, including checking bags, and I arrived at 4:30 a.m. The airport was a zoo, with check-in for American wrapped around the terminal. Fortunately I was flying in a premium cabin, and I’m a lifetime elite in any case (thanks to American’s policy of counting all miles ever earned in an account, not just flight miles, towards million-miler status). There was only one person checking IDs at the TSA station, feeding into several x-ray machines for the pier out of which American operates. So the line to get up to a scanner was long. Past the screener and up to the lounge shorlty after it opened at 5 a.m.

Flight up to New York was uneventful, as was the AAdmiral’s Club at JFK except to say that the lounge was expansive, had computers, and perhaps the worst tasting coffee that’s ever been brewed. Flight down to Barbados was utterly uneventful as well, though I still find American’s premium cabin food to rank towards the bottom of the major carriers. United’s is better, which is truly saying something.

Another American flight arrived at much the same time as ours, parked just farther from the terminal than our aircraft did, and their passengers were bussed to the immigration hall — just beating us as we were instructed to walk. This created a bit of a line, and the immigration folks were in no hurry to process, still we were cleared through immigration in about 20 minutes. And we then proceeded to wait more than an hour for our bags. Mental note not to check luggage into BGI ever again if it’s possible to avoid it (as a bit of careful packing on this trip would have allowed).

Cab out to the hotel, and efficient check-in. The cab driver said the Hilton was his favorite property on the island, remarking impressed that “you don’t even have to carry your luggage!” I guess he’s never driven anyone to Sandy Lane, though perhaps with the new Four Seasons he’ll manage a new favorite property.

We were checked in right after a bevy of British Airways crew, given keys to our ocean view room and told about the Executive Lounge’s offerings. (I could have checked in at the lounge, but didn’t yet know where to go and this was just as easy.) Given a tour to the room by the bellman taking our bags, he proceeded to describe literally everything about the room, fretted that the ironing board was missing and promised to bring one right away! I assured him that wouldn’t be necessary and we were finally in Barbados, in peace.

The beach is at the hotel was nice, and relatively uncrowded for a December weekend. There was a hotel attendant available to help set up beach chairs, and once set up you find yourself looking out at water a lovely turqoise.  The beach is the highpoint of the property. The room furnishings and décor are not really to my taste, but then it’s a Hilton and it could have been just about anywhere in the world.

The staff is all friendly, but this is the Carribean so service isn’t great and certainly not fast. Lunch by the beach meant extremely slow service, they didn’t bring everything I ordered, forgot to once I asked for it, and only felt empowered to comp me a drink by way of apology (manager took my entrée off the bill without my asking, once he came out).

The executive lounge is too small considering the number of people with access. The top three floors of my tower, and top two of the other tower, all have access. The complimentary breakfast spread is nice, but the lounge is busy. I much preferred taking my breakfast downstairs, you can do the full buffet for just a US$10 upcharge over the complimentary lounge breakfast. And the coffee is very good, perfect for sitting outside and relaxing over a long meal.

One feature of the executive lounge is complimentary wireless internet. They give you an access code and it’s valid for 24 hours, and they tell you it only works in the lounge — which is true, if you first use the code from the lounge. But if you take a code down to your room it will work there, giving you complimentary in-room internet which otherwise requires payment. Each day I asked for a code for myself and one for my wife so that I had a few extra codes to bring back to a colleague who would be visiting the property a couple of weeks after me.

Breakfast was the only decent meal on property, and even the buffet was far from outstanding. The food by the beach wasn’t just slow, it was mediocre. They seem to serve the same food as room service, and draw from the same kitchen. So it’s best to go off property for meals. We had an inexpensive ‘fried bar food’-type meal one evening at the Waterfront Café, and also a dinner at Daphne’s.. which was absolutely beautiful, right on the beach, truly top notch service… The food was almost very good but always seemed to just miss, such as my foie gras which was ever so slightly burned.

I was certainly happy here for the price, I paid about $100 a night for an oceanview room with lounge access. So ultimately no complaints for sure! But it was hardly the perfect experience.

Off to the airport, I discovered a lounge airside that I hadn’t been aware of. It’s shared by several airlines and I walked upstairs and asked how I might have access. They ran down their list of associations, and stopped at Priority Pass and I quickly produced by card. The lounge was rather stylish, the automatic latte machine provided good coffee, and the reading material was ample. Food was limited, and it was a morning flight, I didn’t sample any of the mid-shelf liquor.