Hello Zor47.
I've written this elsewhere, but I'll repeat it. I am 51, overweight and blind. Do I feel safe in C.R.? Yes, around 99% of the time.
Here are a few security tips. The list isn't exhaustive, so please read/absorb as much as you can on the Forum here.
1. At night in particular, take legal, licensed metered taxis everywhere, even for short trips. Taxis in San Jose are very inexpensive. The licensed cabs will all be painted red, have a yellow operator's license decal prominently displayed, and will have a taximeter, called a "maria" by the locals. Do not walk anywhere alone, especially at night.
2. Find a wingman or wingmen to explore with. It's amazingly easy to connect with wing men; just visit the Sportsmen's for Happy Hour, also the Hotel del Rey/Blue Marlin Bar around the same time. Depending on where you're staying, you'll probably meet other CRT'ers at breakfast; the Amistad, Castillo, News Cafe (Hotel Presidente) and the Sportsmen's are all good spots to meet other hobbyists for breakfast.
3. Know the "Gringo Gulch" area. A copy of the map (available to paid members) will be a huge help in this regard.
4. Do you speak Spanish? No? Well, many of us do. Don't be afraid to ask a brother for help!
5. NEVER (shouting intentional) wear flashy jewelry or watches, designer sunglasses or any other obvious outward sign of wealth. NEVER carry more cash than you'll need for an outing; leave the chica's salary locked safely in your hotel room lockbox. For most outings, $20.00 - $40.00 is a good amount; food and cocktails are not terribly expensive, taxis are inexpensive etc.
6. Most chicas are fairly honest if you don't tempt them by stupidly leaving money out, etc. but there are of course a few bad apples. Use your instincts here; if you're observant, you can spot trouble signs before even taking the chica back to your room. About chicas: I have NEVER had trouble with any girl I've pulled rom the freelancers at the SL and certainly never in massage parlors.
7. Beggars can be repelled simply by a firm "no." Simply walking with purpose and looking straight ahead as you pass them will often immunize you against their advances. Under no circumstances get violent or aggressive with these beggars, but be firm and keep walking if they confront you.
8. Pickpockets: Carry your wallet in a front pocket, carry only as much cash as you'll need, don't flash your bankroll. Don't allow anyone to get close to you on the sidewalks. Keep moving. Leave your passport original, your credit cards and other important documents locked in your room safe. A photocopy of your passport I.D. page and most recent entry stamp, along with the boarding pass from your flight into C.R. is legal proof of your identity and tourist status. Don't let any cop tell you otherwise. It's the law.
Most importantly, don't be afraid. Be circumspect, observant, cautious...but don't be afraid. And BTW, 9-1-1 works the same in C.R. as it does in the U.S.A. Spanish is helpful here as well, but some of the 9-1-1 operators are reported (Fodor's) to speak English.
Have fun! And, again... read the forum to learn as much as you can before your trip. Buena suerte!
