Ok, so if I understand you, you want some info on SJO, Jaco, safety, MP's, P4P places and driving.
First, San Jose is a great party town for whatever you want.
Where to stay in San Jose for a first timer who wants to be near the action, I would suggest either the Del Rey, (crappy hotel but it "IS" the action) Sportsmens lodge, more laid back with working chicas in a great mongering environment, the Sleep Inn very near the Del Rey/Blue Marlin Bar which again is where the chicas are as well as most of casinos. Sportsmens might be tough to get a room at this stage but you never know. The Mansion wing is where you want to be as the rooms are nicer and it's more tranquil than the courtyard at Sportsmens. La Amistad is a great place but for a first timer you'd be better served at any of the other aforementioned.
Where to go: MP's There are higher end and lower end, Hotel Little Havana formerly known as Zona Blue used to be the best place IMHO for women and a great time, today it's a hit or miss. Nice bar but pricey, good rooms and you can find some really fun girls there. Roughly $55 for an hour unless you're CRT VIP and that knocks off about 8 bucks or so. Another must see is New Fantasy, AKA the Fishbowl because the chicas sit on couches and you can look thru a glass and see if anything tickles your fancy. The rooms are below average to average, price is less than HLH, they have a steam room if you're interested but shower is not in the room. This place is very near the Sportsmens, an easy walk in the day time. A 3rd would be IDEM, I haven't been but the board discusses it favorably asie from it's cost which is a little higher than some others. As for P4P the primary place is The Del Rey / Blue Marlin hotel and casino. This is something every grown man should see once in his life. Open 24 hrs but best around 8pm to 12am or later on weekends. Directly across the street is the Key Largo bar which you'll see chicas go back and forth from the Del Rey to KL all night. If you like music or dancing this is a cool place and the girls are sometimes a little more laid back here. The 3rd P4P is The Sportsmens Lodge. Chicas do work daytime but it's best around 6pm til 11 or 12am whenever the bar closes.
As for Jaco, it's more sketchy at night than SJO IMO but if you take a cab everywhere at night,(1000-2000CR anywhere in the town) you'd be fine. The Beatle Bar has changed in the past year and the town has changed alot in the past 6 years. The Beatle is "THE" P4P scene but chicas can be found next door at the Monkey bar (younger crowd and more hoodlums) and really anywhere they serve alcohol or dance. Some places are fun to dance if you bring a chica in and like to party. They pat you down upon entry at alot of them, if that bothers you, don't go. Most of the girls from BB move to Nacho Daddys when the BB slows down or closes for the night but there are Discos and bars off the beaten path but i'd stay close to the BB if I was solo and was a first timer. Backyard Bar a little further south (10 Min) in Hermosa, and is good on Weds and Saturdays I think but ask someone before you go about which nights.
Regarding safety, don't flash money, jewlery, have a big mouth, walk at night by yourself, get hammerred and stagger around and you should be fine. I have NEVER had a problem in either SJO or Jaco although once in Jaco a couple of trannys tried to pk pocket me thinking I was drunk. I'm 6'1" 205lbs and pretty fit and when I grabbed the wrists of one of them and tossed him into his pal, I quietly said don't fu*kin touch me, they went on their way. I was by myself, walking late at night so it wasn't the smartest thing. Take a red "legit" taxi at night and it's very safe. If you stay downtown in SJO at any one of the places I mentioned DR or Sleep Inn, you wont have to go anywhere else at night. ie; no need for taxis. SL requires a taxi ride to get downtown at night. It's an easy walk by day. Jaco is a beach town by day, walk where you want but take a taxi at night. As for renting a car, good luck. The drivers in the city are horrendous. The drive to Jaco is winding thru the mountains and can be dangerous but take your time and as long as you're outside the city it's cool. I hire a driver to Jaco then rent once I get there. Coastal driving is very easy. Take all the insurance they offer cause they look for everything when you return the car. Had a cop shake me down years ago while driving but nothing in the past 5 years or so.
If I were setting your trip, I would say in San Jose, stay at Sportsmens (no Chica fee) and great guys at the bar with tons of info and most likely a wingman. Find an experienced wingman and listen. If not then the Del Rey (small Chica fee 10$ per girl) or Sleep Inn (25$ chica fee) but very safe. Use a taxi in the city and only rent a car from the airport which places you outside the city closer to Jaco when you're ready to go. In Jaco, stay close to the Beatle Bar for girls, if you drive, park close to the front and take your chica from there to your rental. You say you have a condo, if it's in the city you're set but some of those are outside the city which isn't ideal. I stay at Canciones del mar in Jaco, on the beach right down the street from the BB. Close, safe and a great value. If you bring your girl from the city then it's no sweat cause you probably won't hit the BB. Not sure i'd take a girl i'd never spent time with although price was very good. Use common sense and you wont stand out that much, there are alot of us 6ft+ blonde gringos over there. Knowing spanish is a big plus. I'll be there with 2 wingmen from the 11th thru the 15th, staying at La Amistad, will be at SL for drinks on the 12th around 8pm. I'll be the 6ft gringo, blue eyes hanging with the chicas and my boy who looks like across between Jayzee and Obama. Say hello if you're there. Hope this helps, Bueno suerte amigo
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