After Sam and Dean burned the rabbit paw, which brought them luck before, they still had some lots they won and now actually had a lot of money.

Since you've been wanting to go somewhere to the beach for such a long time they decided to fly to hawaii with you. It was quite expensive but they had the money now so they thought it wouldn't hurt to take a break and actually go to a nice place.

Dean was really looking forward to the beach and the "good views" he would get soon. He probably meant girls in bikinis though. Sam meanwhile was really excited for good weather and going swimming with you.

The three of you were currently sitting in the air plane, waiting for it to start. Sam was reading something while Dean was blasting metallica in his headphones, trying to distract himself from his fear of flying. He said it calms him down.