Just got to the JW yesterday and it is my first time in Costa Rica so I thought I'd post for those people that are also coming for the first time.
BTW, used the nonstop Delta flight from LAX. If you can handle redeyes then you'll love the flight because it is fast. We actually got in about 20 minutes early, something like 6:30am.
It took no time to get through Immigration. There were around 5 agents there to help the flight out. We were the only flight to arrive at that time however I saw a Continental and other Delta plane on the tarmac.
Ten steps from immigration is the baggage carousel. It's the noisiest thing ever. Then another ten steps and your past customs and out in front.
We rented from Avis. If you are in a rush then this is a bad choice as they don't open til 8. There were plenty of legit taxis (the red ones) and guys holding their taxi signs when you walk out. Dollar, Alamo, National were already there to pick up people. Avis ended up coming by around 7ish. Wasn't bad.
It took a long time to get the car at Avis! Be prepared before you get there. Find out if you credit card covers your CDW insurance before arriving. Get the GPS from Avis. Not needed yet but it works and gives you that sense of comfort if you are a first time traveller here (like us). BTW, It's a Garmin Nuvi. Avis rented us a diesel Mitsubishi medium-sized SUV that is an automatic, whereas the website said manual.
Then we hit the road. We were kinda worried about the driving conditions but I was pleasantly surprised. The road from the airport (Avis is outside the airport on the main road) is smooth. Nothing abnormal from the US. It's a 2 lane drive all the way here.
We thought the biggest things to watch out for were the Tico's passing at anytime, the ditches instead of paved shoulders and people lining the road. The cars and trucks seem to drive much faster than the posted speed signs. For example, in front of the airport the sign clearly says the speed limit is 60km/h and we were easily being passed by cars going at lease 80.
They also pass one another frequently and with minimal views and passing time. Sometimes the road becomes 3 lanes. But never did we feel very unsafe on the road. It's just different. I also noticed that it wasn't just the Tico's doing the passing but also the other tourists! I think as we drive here a few times we'll start driving the same way. :)
Again we didn't find it unsafe to drive here just different.
There are road signs that direct you toward towns, so make sure you know which towns are along the way toward the hotel. We started by following the signs to Tamarindo. Then there were signs to Hacienda Pinilla. The Hacienda Pinilla signs WILL take you where you want to go. The GPS is pretty accurate. It only tried to take us on an old route once on the property. Once here, just follow the map given to you at the gate. Once at the gate it is still 5 minutes or so to the hotel.
Every was paved EXCEPT for about 3km. From the turn to Tamarindo to the turn for Hacienda Pinalla. The unpaved part is VERY bumpy like other posters say. And the ticos drive fast on this part too. No real pot hole issues until after the turn to Hacienda Pinilla. Then watch out, they'll eat your car. :)
It took us 1 hour and 15 minutes from Avis to the JW.
Let me know if you have any questions.