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San Juan Weekend

Posted Feb 14 2013 9:51pm

Well, it’s another day and I’m on another flight. This time, though, the destination is for pleasure, not business!

Back in December, a few of us started talking about how much fun it would be to surprise our dear friend Theodora with a birthday surprise trip somewhere to celebrate her 30th birthday. We brainstormed different destinations across the US, Mexico, and Caribbean before settling on San Juan, Puerto Rico.  Over the years Theodora and I have traveled quite a few times together and  hopefully this will be no different. Just like in Las Vegas and St. Croix there will be lots of sunshine, delicious cocktails, time relaxing, and at least a dance party or two.



San Juan may seem like a bit of a random location but in reality it will hopefully be perfect. Here are a few things that went into our decision:

  • How long does it take to reach from New York City? Are their direct flights? Are the flights reasonably priced? San Juan is a direct flight from New York’s airports and at just under 4 hours it is short enough for a long weekend. The flights tend to hover around $299-$400 depending on whether it is a holiday weekend and how far in advance you book. 
  • Will it be warm enough to relax pool or beachside in the middle of February? Yes, luckily when we called a few hotels and checked online everything pointed to 85 degrees and sunny even for this weekend. None of us wanted to pay money for overcast and temperatures in the 70s which is what we feared if we booked a trip to Florida or the Bahamas.
  • Is there more to do then just relax on the beach? While I love a great beach vacation as much as the next person, we knew that each person in our group would have different tastes. Therefore, finding an island or destination which features either a city to explore, a rain forest to hike, kayaking, or other activities would make the trip easier for a group. I have to admit though, after all my traveling this last week I’m actually looking forward to as much beach relaxation as possible.
  • Can we find a beach front hotel which will allow us to stay in one room? This trip is a small trip and therefore we thought it would be more fun if we could share a suite for the weekend. Many hotels don’t actually have rooms that can accommodate 5-6 people comfortably so this helped us easily narrow down the hotels.
  • How far is the beach and resorts from the airport? This sounds weird but many tropical locations require a good amount of travel time between the airport and the resort areas. Since we were only planning a 3 night trip the closer to the airport, without feeling like we were next to the tarmac, the better.


Once we figured out that San Juan would be the best destination we spent a days researching hotel options thanks to Expedia, Kayak, and taking advantage of our group’s multiple hotel loyalty programs. We looked for a resort versus a bed and breakfast since we’re going more for a fun, party type weekend than pure relaxation. We also wanted to ensure we felt safe and therefore trusted a resort which would allow for private beach and pool space. While we will most likely go out in Old San Juan multiple nights it’s nice to know that our resort has multiple restaurants and even a dance club if we choose to stay on site.

Our itinerary is very flexible for this trip which is nice but also a bit nerve wrecking for me, a very Type A personality. I’m hoping that even though it’s a holiday weekend we can squeeze in dinner reservations at least one night at Marmalade or Dragonfly , two restaurants which have been recommended to us by multiple people.

So now, if you’ll excuse me, it’s time to go downstairs and toast the birthday girl with our first glass of champagne!

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