Programs: AA CK/EXP/1MM, UA Conscientious Objector, Hyatt CC, SPG Plat, HH Diamond VIP
Hi. Cayman is great, but I actually prefer SJU. Aside from this being a US territory not requiring passage through immigration/passport control, I really enjoy Puerto Rico as a place and people. San Juan is a vibrant city with a stunning old quarter, fascinating history, wonderful beaches, great hotels (in San Juan proper, I recommend the ritz Carlton or El San Juan for families) and unbelievably delicious food. Outside of San Juan, you have other choices that are more island paradise and less urban beachfront...I really enjoy Fajardo and the hotels there...the El Conquistador (a Waldorf-Astoria Collection Hotel and a part of Hilton) is a great hotel for families, although the service can be spotty at times and you need to choose your accommodations carefully to fully enjoy the location. It does, however, have its own private island, and is located within striking distance of the bioluminescent bay and El Junque rain forest. If you stay there, you MUST leave the property...at least for dinner or lunch...there are some outstanding choices, and I would argue that La Estacion (the station, located within 10 minutes of the property) is one of the best dining experiences I've had (and I have racked up 50+ Michelin stars in my travels.) If you wanna splurge on the hotel, within El Conquistador is the much more private and truly 5-star Las Casitas Resort (also Waldorf-Astoria Collection)...my preference, but comes at a price — especially during peak. All of these properties include dining, pools, water sports, beaches, spa and casino. El Conquistador/Las Casitas has a world-class golf course. Finally, you can do one of the new properties recently (past 3 years) developed on Vieques —.including the new W hotel.
As for AA...at present they have one non-stop—.leaves early morning and returns late afternoon so you get there early and leave late...flight time is roughly 5 hours on a 737-800. There are also a very large number of connecting flights as SJU is the AA hub for caribbean flights.
Realise this is less about AA and more about the destination...but then again, you asked Hope this helps.
Programs: AA EXP, LFT PLT, Admiral Club National Car E Hilton GLD Hyatt PLT Club Carlson GE Marriott SLV
Originally Posted by kooju999
Our dates are kind of flexible since my son's winter breaks is Dec 22,2012 - Jan 5,2013
Travailen said it best when he recommended SJU as a destination. My hometown. Not to be favorites, but what exactly you are looking for? I mean, they all have beach, great golf, scenery, etc. However, while you mention that your dates are flexible, you are still traveling during PEAK time, x-mas is one of the more expensive times of year to visit the Caribbean, airfare and accommodations are high during that time. If I'm correct, AA only has one direct Caribbean flight, to SJU, all other flights, to other Caribbean destinations will involve a connection in MIA.
SJU will probably be the best bet, no customs, lots of flight options, and also offers the possibility to do some day trips to other islands. I suggest you check the travel section tab on this board and look at Caribbean, there are numerous post in there. You can also go to your local library and pick some Caribbean destination books, read it over the weekend and see what areas appeal to you. Cayman Island are nice also, also the Dominican Republic, St Thomas, St Marteen.
Happy travels and enjoy.
Master of my thoughts, slave to my words....
Programs: AA EXP 2MM, Lifetime Platinum, HH Gold, SPG Gold, Travelers Aid JFK Volunteer
I recommend Barbados for families, couples, and solo travelers alike. My family has owned a house here for 60+ years, yet we never tire of coming. Unlike some other islands that are pretty much just artificial resort culture replicating U.S. resorts, Barbados is a real country with a distinctive flavor combining British, Canadian/U.S., and Afro-Caribbean cultures. Barbados has a rich, vibrant history like Puerto Rico, and has superb, well-maintained historic sites, as well as ecotourism, nature preserves, animal attractions, and much more! The food is incredible too!
It is also worth noting that because Barbados is so far to the south and east in the island chain, it is out of the path of most hurricanes, and it also has no malaria or wild snake population. It is a well-educated, prosperous country with relatively low crime rates, and virtually no violent crime. (for the worry warts)
Barbados is accessible easily on AA from JFK, MIA (2x daily), DFW, and SJU.
Let me know if you decide to visit the island, and I will PM you more info!