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Hey, Sam - I just made the exact same trip, with two nights in each place, and I can tell you, you'll be okay on your own. The Sportsmen's was really legit and the rooms were surprisingly good. Definitely get rooms there.
You can take an UberX to Jaco for about $80, but if you're on a budget, the bus from downtown SJ is only $5. It'll take about 2.5 to 3 hours.
I didn't stay at the Cocal, but it's easy to find and the pool bar is definitely worth checking out. On the 4th of July, it had more women than you could shake a stick at. It won't be like that where you're there, but there's still plenty of talent.
Since you have a bachelor's party, I highly recommend getting a condo at The Palms condos,right next to Crocs. You get a wrist band that lets you use the pool and bars at Croc's, which is nice, but, more importantly, the security guards at The Palms do not give two sharts about bringing in chicas. I preemptively gave the guard a $10 when I checked in, and he was more than happy to let me bring in whomever I wished. They'll just hold the chicas' IDs, which is a good thing, because that means they can't leave without you and get their ID back.
My last night was back in SJ and I stayed at the Gran Hotel. I'm a hotel snob, but even I was impressed. They bellhop downstairs told me they charge a ridiculous $140 to bring a "guest" to your room, but he then told me after I gave him a five spot on the way back in that I could just take chicas to the bar upstairs, which is out of line of sight of the front desk, and then take the chica back to my room from there. I was out of gas by that night, so didn't party. But I'll be interested to hear if anyone gives that a go.
All in all, CR was super chill and easy to get around. You'll be fine. That said, It's worth hitting up Pops (his handle here) if you're just nervous and not used to moving around in Latin America.
Cheers,
GPd
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