
Welcome to: Where I Spent My Week Off —by a NYC Restaurant "Insider"
So, what do you do in the industry?
I’m a real estate investor, developer and entrepreneur with considerable financial interest in the F&B industry.
And you have how many weeks off a year, generally?
I tend to take a lot of shorter trips throughout the year, about every 8 to 10 weeks.
What made you choose Costa Rica for this vacation?
My wife has a very good friend in Costa Rica (who also happens to be a restaurateur). She’d been planning a visit for several months, but I convinced her to postpone it for the holidays so we could travel there together. I’d been to Costa Rica several years ago and was curious to see how it had changed and/or developed. Plus, since we were planning to be away for the New Year, I thought it best she be able to celebrate with her friend, as that can make all the difference for the holidays.
And where did you stay?
Since my wife’s friend is based in Tamarindo, we chose the best hotel we could find closest to her friend’s home, which was Tamarindo Diria. It turned out very well, because we were a mere two blocks from her restaurant, and only five blocks from her home. It’s also quite centrally located, directly on the beach, with a lot of places within walking distance.

How was the ambience/service/amenities etc?
OK. For the price however, it was extraordinarily impressive. Any traveler would be hard pressed to find those accommodations at that astoundingly low price (especially during the holidays) anywhere in the world— except perhaps in Las Vegas (where the rooms in all the luxury hotels are essentially loss leaders).
Also, the food at the hotel wasn’t very good, so luckily there are numerous commendable places to dine very close by: Wok ‘n Roll, Carolina’s, Le Beach Club and El Coconut were all exceptional.
Any major glitches and/or disappointments?
The only major disappointment was that the two (other) restaurants our friend recommended to us (Paola’s and Nogui) were both closed on New Years day, and we weren’t able to rearrange our schedule to fit them in to try them. Oh, and for some reason, Tamarindo Diria was forever running out of towels.
Plus, we did have one incident where an errant forceful wave pushed my wife onto a rock and she scraped her foot and leg. She’s a trooper though, and thankfully she wasn’t hurt badly. It was a pretty good reminder that one must always be very mindful of the power of the ocean.
Any great standout experiences?
I think the trip overall was a standout, one of the best we’ve ever had. We got to meet another new friend on this trip too, and it was really wonderful and special to spend the time with them.
We also rediscovered a great modest little restaurant I first found years ago on my previous trip (Hotel Las Tortugas), and we absolutely loved its simplicity and rustic charm. We had two perfect lunches there (even though it was a good four mile walk down the beach to Playa Grande).
How much did you blow all week?
Unfortunately, I wasn’t able to plan the trip far enough in advance, and the last minute booking cost us pretty dearly. We barely managed to snag two available seats at $1200 each (economy; business was unavailable), which didn’t include a small domestic return flight from Liberia Guanacaste to San José ($115 each). The hotel was about $200 per night (including breakfast), and food/drink per day was probably about $200 averaged (including some dinners with friends). Other activities (sailing, equipment rentals, etc) was perhaps another $600 total.









Welcome to: Where I Spent My Week Off —by a NYC Restaurant "Insider"
So, what do you do in the industry?
I was a General Manager/Maitre d’ for an [popular] restaurant in Tribeca, but I left there about a month ago. I also used to be a managing partner for a Midtown restaurant several years ago. I’m currently on hiatus until the end of January.
And you have how many weeks off a year, generally?
I generally take about 4 weeks off a year, but not in succession.
What made you choose Virgin Gorda for this vacation?
We weren’t able to book the trip that far in advance, so I guess our first priority was finding something that was available, nice and not too expensive considering the such late notice. I do have a travel agent and she recommended it according to my needs. We also didn’t want to travel too far and have a very long flight or a lot of connections. However, it still took almost 12 hours overall, because we had one connection and a boat ride.
And where did you stay?
At Little Dix Bay, which I think was originally built by the Rockefeller family. I did hear of Little Dix Bay prior to this; I know it was a super hotspot maybe 20 years ago. A friend of mine told me he visited there briefly around that time— he was sailing the Caribbean with friends and they dropped in there for a drink, and he loved it.
How was the ambience/service/amenities etc?
Not bad. However, the resort does seem to be a little worse for wear and could use some sprucing up here and there, especially the rooms. Also, it was a lot more family-oriented than we were led to believe, but that could also have been exacerbated because of the holiday. The beach was lovely, though.
Any major glitches and/or disappointments?
Our first meal upon arrival was at the more casual restaurant near the dock, and that was awful. The service was incredibly apathetic considering the cost of the resort as a whole. The food was pretty terrible, too. We decided to just avoid that place for the rest of the trip which affected our overall spending, because it was the least expensive dining spot. Also, if you chose not to partake in the very very expensive (!) all-you-can-eat/drink New Years Eve buffet, there were no other options for dining than room service. There must have been some kind of lesser surcharge for the buffet upon booking, because I find it very hard to believe a lot of those families (of 6 or 8+ people) paid that astonishingly exorbitant price per person for the experience. We could eat at Per Se for that kind of money.
Like I said, I also thought the room was shoddier than advertised. There were cracks in the walls and bathroom tile, for example, and the linens were cheap and worn out. There’s no TV and no dock for playing music, so late at night if we weren’t tired, we had to resort to watching movies (which we had with us) on my laptop.
Even the beach experience was somewhat strained, as these families get very territorial and downright rude about "their" little area with "their" lounge chairs and tables. So in that sense, the resort should have been better prepared for the upswing in holiday traffic and provided ample accommodations for everybody.
Any great standout experiences?
The water is the clearest and most beautiful I have ever seen in my life. It was the one thing (aside from my companion) that salvaged the trip and made it all truly worthwhile. I’m an avid swimmer, so being able to swim in the sea that was as warm, clean and placid as a pool was wonderful. The prevalent stingrays are a little scary though, but thankfully, there were no bad incidents.
Also, the complimentary daily afternoon "tea" was a nice welcomed touch. Perfect for the sunset after a day on the beach, right before freshening up for dinner.
How much did you blow all week?
The airline tickets were about $700 each. And the room was about $650 per night. Food/drinks every day were probably about $150 per day (but breakfast is included with the cost of the room).





Welcome to: Where I Spent My Week Off —by a NYC Restaurant "Insider"
So, what do you do in the industry?
I’m a bartender, but I’ve also worked as a waiter. I’ve been in the F&B/Nightlife industries for about 14 years for various [very popular] places in NYC.
And you have how many weeks off a year, generally?
I don’t get paid vacations, but I do try to take off at least 2 or 3 weeks a year if possible.
What made you choose St. Lucia for this vacation?
I usually like to travel to warm places in the wintertime. My girlfriend’s family is from St. Lucia, so she was visiting them for the holidays already. We arranged our trip so that I would fly to St. Lucia to meet her there later, and she came to meet me at the hotel we booked especially for this occasion.
And where did you stay?
At the Jalousie Plantation which is currently being run by Hilton hotels. A friend of mine had recommended it since he’d stayed here several years before. It sounded great, but from what I gather, it had previously been privately owned by a somewhat eccentric English gentleman. My friend had gotten to meet him on his visit, and he said it made the experience a lot more charming, as he was invited to a private party thrown by the owner on the property of his personal home on the resort. Unfortunately, we didn’t get to have the same experience.
How was the ambience/service/amenities etc?
Overall I’d say very good. Our room was beautiful, but we got lucky, since apprently they are in mid-construction to convert Jalousie into a Tides hotel, and we received a room that was already renovated. The construction noise was irritating at times, but it was sporadic enough not to affect the trip that badly. The service was all right, but I’ve traveled to the Caribbean before, and it’s somewhat to be expected that everyone and everything moves much slower than New York, but mostly everyone was very warm and friendly. The food was a standout, as it was quite good, which is another thing that doesn’t come easily in the Caribbean. Aside from the fresh seafood and amazing fruit, I even had some American staples like the burger, and that was much better than I had expected.
Any major glitches and/or disappointments?
The only thing I can think of is that the long ride from the airport is a major pain. It’s about an hour’s ride since it’s slow-going at times over the rough terrain. I tried to book a helicopter for the return trip, because I was so not looking forward to the ride out. I was happy to see that the cost wasn’t prohibitive, and I booked a reservation, but at the last minute the pilot just decided not to fly so that was a major disappointment.
The other thing is that you have to get up very early and be aggressive if you want to save a first-come-first-served "cabana." Luckily, my girlfriend is an early bird so it worked out great, but the beach does get crowded all day every day. People move into their cabanas at sunrise, and it seems like they don’t move out until they check out.
Any great standout experiences?
We mostly just laid around the whole time, as my girlfriend isn’t so into hiking or other activities like that. She does waterski though, and the great thing is that local boats are always hanging around that will just take you out randomly on a whim. They also do tube rides if you’re into that sort of thing.
Also, the fireworks show on New Years Eve was nice. Being there in the sand watching fireworks on such a warm gorgeous night with my girl felt really great and special. And some of the people we met there were nice and cool too.
How much did you blow all week?
Ha ha, I don’t even want to think about it. But the room rate was lower than I’d expected. At first I thought it was due to the economy (as usually places will jack up the prices quite a lot for the holidays) but now that I think about it, maybe the reduced rate was due to the fact that the resort was under construction in some areas. My flight was about $750 economy, and the room was around $600 per night (but I think it’s normally around $900 for the holidays). We didn’t have an all-inclusive plan (but breakfast was included), so we probably spent about $150-$200/day average on food/drinks.







