www.CostaRicaTicas.com

I can already see one comment coming Surfing and partying will be plentiful in Jaco along with plenty of available women. If your experienced in surfing I would highly recommend taking the 5-8 min drive south of Jaco to Playa Hermosa as the waves and the beach are much better there. Seems you want to do quite a bit and it can be hard to squeeze it all in a week trip. You will have a lot more fun on the mongering side of things in San Jose, however you will be a over a hour out from fishing or surfing. I would spend at least 2 nights in San Jose and hit all the main spots like Hotel Little Havana, Sportsmens Lodge (both good places to stay also) Key Largo, Hotel Del Ray, New Fantasy.. all places where you will find plenty of women and lots of partying. I don't know the hotels in Jaco but if you wanted to get in some adventure tours and fishing/surfing its your best bet because it has access to it all. Cocal Casino in Jaco seems to be the recent hot spot for the girls to be at night.
If you don't mind staying in Playa Hermosa there is a small hotel called Rancho Grande that is super cheap $15 a night if I recall, and your 5 min from Jaco. If there was one thing I would highly recommend you do on the trip is swing by Hotel Little Havana, the place is really so much fun it is beyond words and the selection of girls is very very good.

That's plenty of $$ for a week or so assuming you don't get crazy or go fishing with just the two of you, do-able if you can hook up with 2 others to split. Fishing is pretty cheap (compared to US), but not dirt cheap, so that'll hit your budget. There's a fleet out of Los Suenos resort near Jaco, and a bigger fleet in Quepos, 1 hr south, cheaper. But look at http://costa-rica-guide.com/travel/inde ... &task=view. It rains alot in Sept, often not the whole day or maybe skips a day, but when it does it's a sight to behold--you may not want fishing in your plans.

You are not going to be able to fly from Jaco to anywhere, closest airport would be Quepos, 1 hr S, but that plan is not good. If you are going to travel around alot, rent a car on the day you leave SJ for the beach, fairly easy to get to Jaco, Rt 27 to Rt 34 to Jaco, and from there you can go around to other places at will. If driving around SJ to Jaco is a bit daunting for you the 1st trip, which it may be, take the bus or Inter-bus to Jaco and rent a car there, return it there, and bus it back. Once you're out of the city, CR is pretty easy driving. Make sure you make your car rental reservations on-line stateside, you'll get a much better deal, and the earlier the cheaper.

Get a good CR map, that will narrow your to-do list. A week goes by pretty fast in CR.

Ask any 10 year-old if they'd like to spend a week at Disneyland........with $1,000 in their pocket.

A wise 25 year-old would have the same answer about a week in San Jose.

RAC

There's a gringo-tico board member that has a tour bus business, puravidatransport, always gets good reviews here, try and find him on the board, hooking up with him wouldn't be a bad first trip.

Worst comes to worst and you spend the whole time playing in SJ, you'll still have a very memorable trip. When you come back, come back in the dry season and explore.

Im in FL myself, what part you live in? I took a awesome day trip back in March. 3 part tour to Doka coffe plantation, Poas volcano, and La Paz waterfall gardens. There are a lot of tours that leave out of San Jose also.

The problem with day trips out of San Jose in September is getting out of San Jose and to some place interesting before the rains set in. The advice of a 53 year old fat guy to a couple of presumably fit 20 year old surfers.

1. You may notice the 2-hour time difference the first few days in that you will wake before anyone else. This will actually work in your favor during the rainy season.
2. Spend Thursday - Saturday in San Jose and monger. If you know any Spanish, visit San Pedro Mall in the afternoon. Catch a movie and check out the food court. If you go to the side of the court (near the garage), you can find mall workers eating lunch at the tables that are not near a major restaurant. They are more likely to respond to a chat-up, but forget about hooking up, enjoy the culture.
3. On Sunday, fly to Tamarindo on NatureAir or Sansa. Book early for the best rate. I have paid as low as $65 and as much as $120. Interbus is cheaper, but about 5-6 hours ride instead of 45 minute flight, and for the most part the bus ride is kinda dull.
4. Stay in a cheap hotel, rent a board (there are lots of shops with a wide range of boards), rent a car/SUV (book in the US, I have used Budget at the Tamarindo airport) . Spend Sunday orienting yourself to Tamarindo. Monday - Wednesday, surf dawn patrol at Playa Grande, Tamarindo, and Playa Langosta. This should give you a nice range of beach and river mouth breaks. Check Google Earth and you can see the geography. You will need to get a short boat ride from Tamarindo to Playa Grande. Use a soft sided cooler from the US as luggage and then load it with drinks/sandwiches/fruit. Plan on surfing until noon. Sleep in the afternoon, then check out the local bars in the evening. Think Daytona/Cocoa.
5. If you happen to hit a dry day (not likely) try to visit Nosara (4WD only) or Samara (no surf, but great beach)
6. On Thursday, head back to San Jose and monger until you have to leave or your johnson breaks.

A little more advice
1. Try to book your first weekend at HLH, take advantage of the extra low rate (for hotel guests), to sample multiple girls. (threesome, foursome, fivesome )
2. Try to book your second weekend at SL. More of a clubhouse and goodfellas vibe.
3. Book a return trip before you leave (most important point of all my ramblings).