www.CostaRicaTicas.com

Finally, a needed getaway is booked for 12/27-1/1. Plans are to stay at Castillo in PH 12/27, at a Chica friendly AirBNB or Hotel Jaco to enjoy the beach and the "scenery" 12/28 and 29, then back to Castillo 12/30 and 12/31. RIP Pops, he was going to be my tour guide on first trip, but feel pretty comfortable from all of the great information all post on this board. But always open for pointers, to meet anyone else down there during the same dates, and also for contact information/Whatsapp#'s for solid providers there. In the unlikely event I find a winner on night 1, I might take her to Jaco for one of my two nights there (but maybe not...keeps me from scoping out the talent there...but if I like her enough and the price is right, we'll see).
Any tips or #'s appreciated. Looking forward to it!

You are kind of defeating your purpose of going to Jaco if you bring along a chica from SJ. For what you you have to pay her for her time as well as food and drinks, you could probably get a couple of great sessions with the best that Jaco has to offer. Also it looks like you are only in SJ for a single night before heading to Jaco. Not really enough time to evaluate whether you want to be tied to her exclusively for a few days.

Not sure how many women will be out and about between Chistmas and New Years but in my experience there are always enough to have a good time.

You seem to have the First-Timer, OverPlan, OverThink jitters. No cure but the first trip. Try not to lock yourself into a schedule pre-trip. Once you are on the ground, bounce around to see where/if any action is happening. First night in San Jose, I suggest Sportsmens, Taormina, Castillo but don't linger in any one of them longer than 1 hour if there is no action.

In Jaco, the only reliable action is the Cocal and even that is an evening scene. During the day, check out the main drag, especially Jaco Walk and the area around the Rolling Thunder Saloon. Then go to both Caritas and Malecon for a beer beachside. Don't expect to find action, just relax, have a few beers, enjoy the scene. Then clean up at your hotel and head to the Cocal around sunset.

When you return to San Jose, call Pension Monicas or Pension 360 to see if they are open. You will find their listings on Google Maps once you are on the ground. These would be the best daytime bets and the above mentioned hotels in the evening.

In the meantime, monitor the English language web sites QCostaRica and TicoTimes to get a feel for the local holiday atmosphere and events. I often came to CR during the holidays and never had a problem finding action during the dates of your trip.

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If you lose your temper you’re phucking yourself - Garcia Marquez