Do not fly into Punta Islita. That airport is basically for one resort and there are really no taxis or anything else there. Also, the road from Punta Islita would be almost impassable during the rainy season without a 4X4 with a winch and snorkel. The resort is simply beautiful but is for sure in the middle of nowhere.
Nosara would be a better option as it is a larger town (than Punta Islita...still tiny) with taxis and the road from Nosara to Samara isn't as bad as roads to/from Punta Islita. The road between Nosara and Samara is a dirt road with significant holes but any 4X4 should be able to handle it.
It will take at least an hour (and perhaps up to 2) to get from Nosara to Samara so won't be a cheap taxi ride. However, it is probably still cheaper to fly there and do the taxi than driving (either rental or hired driver) from San Jose with just one person. If you have 2-3 people, hiring a driver from San Jose might be less expensive.
My recommendation is go in the dry season unless you are a surfer then the rainy season is usually best for larger waves. But if you are going for surf, the beaches between Nosara and Samara are usually better e.g. around Playa Guiones. This would also save time/money on transport if you fly in to Nosara.
Keep in mind that if you do fly, Nature Air (or Sansa) will not guarantee your surf board will get there. They also have significant charges for overweight bags so pack light. Most surfers opt for ground transport for these reasons. The bus is how most surfers arrive in the area and is a reliable and inexpensive option but would be a LONG ride from San Jose, in the 6-8 hour range.
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