Another important issue with family - time of year. The difference between a rainy season visit and dry season visit is enormous. During the rainy season you will spend much more time in a hotel room staying not only out of the rain, but out of the bugs. Being outside after dark doing anything in the rainy season - like eating dinner in an open air restaurant even while wearing bug repellent - can be a challenge. Especially for those in the party who aren't on the trip for the waves. After a number of summer visits to CR (our summer, July, August, September..), I couldn't believe what a different experience I had when traveling there during the January-March period. You could hang outside after dark and not get eaten alive. The family appreciated not having to put on bug stuff just for a trip to the mercado.And you weren't trying to work the non-surf activities around the weather. Your family could also be stuck on a very rainy and wet beach -- or in a hotel room -- while you surf.