Gino,
I'm like you. I don't a little rain stop me from having a little outdoor fun. I usually spend more than a night or 2 outside the Gulch each trip, but if you're biting off just a little bit more each time of CR outside of SJ, there is plenty there to keep you busy for many trips. During the rainy season the driest place to go is probably to one of the beaches in Guanacaste in the NW part of the country. Unless you fly, thats probably going to be at least a 2 night trip outside of SJ because it's a least a 5 hour drive each way to get back and forth. I'm not a big beach person and general prefer the highland parts of CR more and because of the higher elevation they tend to be a bit cooler than the coasts which is particularly a factor during the summer.
The Fortuna/Arenal area is one of my favorites. You're odds of being able to see the lava flow are greatly reduced during the rainy season, but I go as much for the hotsprings which I enjoy nearly as much when it is raining (like you said, who cares if it rains if you're going to get wet anyway). BTW, that outfit that Blaze mentioned (exploradores) also goes between SJ and Fortuna and is a good way to get from one place to the other if you're planning to do some rafting anyway and want to kill 2 birds with one stone. You could do it as just an overnight but, since you'll be getting in fairly late if you go rafting, I think at least 2 would be better if you want more than just 1 morning checking out what there is to see around there.
Monteverde is another nice area, but requires 2 nights even more so than the Arenal/Fortuna area for 2 reasons. One, its a rougher ride to get there. And two, wildlife viewing is best done in early morning or late afternoon (or even evening) so you'll really miss out on most of it if you bop right in and out. You'll get wet in the rainy season. It is a cloud forest after all and is already pretty wet even during the dry season. OTOH, in some ways the rainy season is actually a little better because you get much fewer crowds.
Other potential places to go include Tortuguero in the north (caribbean side) or Osa in the south (pacific side), but those get particularly rainy during the green season and usually involve having to fly to get to them. Rincon de la Viejo is another volcanic area in the Guanacaste province that will probably be drier than Arenal but like the beaches up there it is pretty far. If you want beaches (I'll assume you've already checked out Jaco) and don't mind the rain (mostly just in the afternoons) and a lot of humidity, my preferred candidates would be Montezuma/Mal Pais/Sta Teresa on the tip of the Nicoya Peninsula, Dominical south of MA on the Pacific side and Cahuita/PV on the southern Caribbean side. Again, unless you fly, each of these are probably at least 2 nights outside of SJ to make the time it takes to get there worthwhile. So with all these you're good for, how many is that, what, at least like 8 more trips?
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