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Trip Report Puerto Rico Escape!

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This has been a particularly horrible winter in Boston, about as cold as any I can remember. Although the snow hasn’t been overwhelmingly bad (there’s still been plenty), the temperatures have been ridiculous, with whole weeks in the 20s or lower. With the onslaught of the polar vortex, and with Jimmy Buffet on my playlist, I realized that “I want(ed) to go where it’s warm”.

So I cobbled together a last minute trip to Puerto Rico – not the cheapest thing in the world, since I was late in the day in booking it, but an escape nonetheless!

I have been to the Caribbean several times, including the Bahamas and Mexico and to be honest, it’s not really my scene – I’m much more of a Key West or Palm Beach girl. But this cold weather has just been too much and it was time for an escape to points well south! So I packed up my Lilly Pulitzers, called my friend Michelle (who also hates the cold and works too hard) and after work let out on Friday Night, away we went for a long weekend of quality beach time on the late night Jet Blue Flight to San Juan from Boston.


Our flight left Boston at Midnight and was scheduled in to San Juan at around 5 a.m. I was exhausted from the work week and had a martini in the airport bar before take off, so I slept for most of the flight, except for when we hit some nasty turbulence down off the coast of Florida. Why is it that nothing can ever be completely easy? ☺ As much as I hate flying (to the point of being scared of it), Jet Blue is a pleasant airline and the flight was on time.

Even as exhausted as I was, and wondering who in their right mind takes a red eye for a 4.5 hour flight, what a pleasure it was to arrive in Puerto Rico! I was still sporting my all business look, having gone to the airport straight from work, but business formal felt much less stiff in 70 degrees and a pair of super duper strength Karen Walker sunglasses.

After a short ride to the Marriott Resort & Stellaris Casino, we made our way to our room. It was nearly 6 a.m. by now and I was exhausted to the core. We hit our pillows and didn’t wake until noon. Feeling refreshed, I pulled back the curtain and voila – blue waves, sunshine and sand beckoned. Although I love my city, it was delightful not to be in Boston!

We had a quick bite at the hotel restaurant on the ground level near the access to the beach – so unremarkable that I can’t remember its name, or even if it had one – and went down to the beach. A helpful attendant brought us loungers and we sat and soaked up rays in peace for the afternoon. I have to say that the beach was far from the best I have ever seen – too many birds (very ugly ones!) flying back and forth! And rough sand! Better than Boston, but still...

After a restful afternoon on the beach and soaking up some good sun, we made our way back to the room to get ready for Saturday Night in Puerto Rico! With the benefit of a full day of rest, I have to say that I was pretty unimpressed with hotel. It wasn’t as clean or refined as I typically expect from a Marriott and the air conditioner was downright noisy! But still, I felt well rested and it felt great to see a lightly sunburnt version of myself smiling back in a black shirt dress from Anatomie and black platform sandals.

Michelle was also feeling chipper and refreshed and we headed downstairs to the bar for a happy hour cocktail. The hotel bar is a nice, open space, with room for a performance stage of sorts, where a band later would play salsa music. The bar was festive and crowded and despite the unknown Spanish language song that was actually playing as we sat there, the song “Boat Drinks” by Jimmy Buffet was looping in my head. We settled in at the bar and Michelle ordered a glass of rose (boring!) while I was in the mood for some rum and ordered a Planter’s Punch (delicious!).

We were in the mood for small plates and tapas and the bartender recommended a nearby restaurant called Bar Gitano, within walking distance of the hotel. From the moment we arrived, we knew it was a good choice – very cozy, nicely lit, with nice looking people eating nice looking plates. We lucked out and were seated on the outside patio, which was very enjoyable as it was a nice evening, the kind that won’t make it to Boston for many months, and we finally felt as if we were in vacation mode. We ordered a pitcher of white sangria and no one rushed us to order as we luxuriated and watched the world go by. The sangria was quite delicious (and surprisingly strong) – by the time our waiter came back half an hour later to take our order, we had finished the pitcher. I am a giggly drinker and I could feel the tickle of the sangria setting in under my shirt collar, but that didn’t deter us from ordering another pitcher, as well as a small sharable seafood paella dish, calamari, some potatoes and manchego cheese, all of which were great choices and very reasonably priced. By the time we left an hour later, our appetites were satisfied, while the sangria had imparted us each with a rosy glow and appetite for laughter.

We contemplated going out to a club in Isla Verde or downtown San Juan for a while, but the combination of pent-up exhaustion, sunburn and sangria had us pretty tired. So we went back to the Marriott Bar prepared to call it an early night. The salsa band was in full swing, and we were feeing very tipsy, so we partnered with each other and hit the dance floor. So fun!

After showing off our moves, we made our way back to the bar to sit for a little. Michelle ordered a Cuba Libre, while I stuck with a glass of water, which I sipped staidly until some goofball from Canada came over and asked me to dance. I obliged him for 10 minutes, but had absolutely no interest beyond that and politely excused myself just as Michelle came to rescue me.

And off we went to sleep.


The next morning we again treated ourselves to a late wake up, which I have to say is sooooo nice and something I can really get used to! (But had better not!)

It was 11:30 a.m., surprisingly a bit cloudy, and we were now hungry for breakfast. So we made our way down to the lobby and, after the concierge confirmed that stores and restaurants were open in old San Juan, we made our way there by a ten minute taxi ride. One fashion tip for any ladies making the trip to old San Juan – it’s not the place for heels! Ballet flats were the right decision!

The driver left us off at a grassy park not far from which was a recommended restaurant called Caficultura. We went in and sat down and had some delightful French toast and coffee. Caficultura was a perfect, coffee shop like detour, and I would recommend it to anyone in need of fast refreshment while visiting old San Juan.

I have to say that I was very impressed with old San Juan. I did not have much in the way of expectations, but the atmospheric streets, cobblestones, pastel colored houses, and adorable art galleries made it a very pleasant place to stroll. I don’t know if there wasn’t a cruise ship docked when we visited or what, but it was pretty serene and one of the nicest towns, with a real street grid, that I have visited south of Florida. Especially memorable was the fort, El Morro, at the end of the town, which was built I believe in the fifteenth or sixteen centuries and gradually expanded on as the years passed. With its green lawn and dramatic position over the water below, it’s a place where a history buff could spend a few hours easily (for us, an hour was enough).

After visiting the fort, we walked the cobblestone streets, including Calle del Cristo, where we stopped in to art galleries. I bought a lovely silver necklace and Michelle bought a small pastel painting to hang on her kitchen wall. I love collecting keepsakes while traveling and would have gone back to this area if we'd had more time in Puerto Rico.

By now the sun was beginning to come out in earnest and we had covered most of the compact downtown area. So we hailed a cab and went back to the Marriott to lay out on the beach. It was a similar experience to the day before – pretty good sunlight, but far too many birds!! But we got tan and that justifies the price of a plane ticket!

When the sun was getting low, we went back to the hotel room to spruce up for the evening. We had a reservation at Pikayo – one of the more renowned restaurants in San Juan, and probably on Puerto Rico in its entirety. Knowing full well that it would be many months till warm summer breezes arrive in Boston, I decided to rock my favorite Lily Pulitzer pink shift dress with a matching lightweight cardigan tied around the shoulders. What fun a girl could have living somewhere where it seldom drops below 60 degrees! ☺

Not eager to test out Puerto Rico sidewalks in our heels, we got a cab to take us down the street to Pikayo. Pikayo is a beautiful restaurant with a graceful bar and great views of the water from many angles. I had read reviews of other travelers who class it among the best restaurants in the world. While I personally did not find the experience THAT amazing, it was still excellent. I started out with a yummy, farm fresh salad, which was aggressively priced at $17 and followed it up by a piece of Salmon (Alaskan King) for $38. While the meal was pricey, it wasn’t crazy and the food, particularly the salmon, was excellent. (Please don’t make snarky comments about ordering an Alaskan Fish in the Caribbean – a craving is a craving, what can I say!). We shared an excellent bottle of riesling with the meal, which wasn’t priced too crazily. All in all, I would probably go back to Pikayo with that special someone next time I’m in Puerto Rico (if I ever figure out who he is!).

After dinner, we hailed a cab back to the Marriott. It was much quieter in the hotel tonight, being a Sunday night, so we parked ourselves at the bar for a drink before trying our hands at lady luck in the Casino. I had a Planter’s Punch, as did Michelle, after which we entered the casino.

“Casino”?! What a disappointment! Just a few tables, slot machines. Nothing really too exciting. But there was a dealer dealing blackjack, a game I have enjoyed for many years since first encountering it at summer camp. So Michelle and I pooled $100 each and walked away with $400. As they say, you gotta know when to hold them, know when to fold them (yes, I know that's about poker).

It was pretty late by now and with our flight the next afternoon, we decided to take our winnings and call it a night.


The next morning we awoke bright and early, determined to go for a jog on the beach and soak up those priceless last rays of sun before heading back to the snowy north. Mother nature fully cooperated on this one and the jog was very satisfying. I don’t know about you, but after two days, if I don’t exercise, I’m not so much fun to be around! (Michelle is the same way).

After our jog, we sat out on loungers, trying not to count down the minutes until our return to gray old Boston. But all good things must end, so back we went to the hotel to change out of our swimsuits. As sad I was to see vacation end, it was fun to dress up again for the trip home – paradise or not, I missed my burgundy theory trousers, and white collar dress shirt from brooks brothers, and my leopard print loafers from Steve Valantne and matching skinny belt. You can put the prepster in the islands, but you can’t take the preppy out of the prepster.

We got to the airport in no time and since I’m pretty terrified of flying, so we made time for a goodbye Planter’s Punch in the airport bar to take the edge off before takeoff. As I sipped it, I reflected to myself on the trip, while Michelle caught up on e-mails. Puerto Rico is a lovely island and I hope to be back here in the land of sweet breezes and warm weather some time soon!

PS – Like the flight down, the flight home was horrible for about an hour and half stretch off of Florida! Does anyone know if this was random or if there is a reason why this seems to happen in this part of the world? The flight was really bouncing, so I ordered a small bottle of Trinity Oaks Pinot Grigio, and soon felt the desired effect of a familiar tickle forming under my shirt collar. When the bouncing refused to cease, I purchased a second bottle and passed the rest of the flight in tipsy conversation with the college senior next to me about her plans for the real world. Best of luck with the start-up, Sara! :)

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