But the search box, it requires educating the user, and this is your initial and most important functionality on your site. The funny thing is, you allow your user to type in the search as if they are speaking to a person which is a great idea and obviously the way it should be, but that is not how users have been trained to interact with random websites. I am sure you are aware of this, I am sure the search box is very important to you, but I think you should revisit the search box and homepage.
Here are some ideas, feel free to love them, hate them, praise them, trash them. I hope they are good and if not I hope they give you some new ideas.
* Home page - plain white & bare, logo centered, add airplane or luggage to logo so you don't need to describe what you are offering, text "Where do you want to go?", text box, and nothing else. (Format it like google and people will be more inclined to use it like google)
* Automatically figure out where they are coming from. Google analytics knows already, so I am sure there is some way to grab that info. Assume this is their starting point until they tell you otherwise. It currently is defaulting to LA.
* The first question anyone answers when traveling somewhere is "Where", thus the only text on your page asks, "Where do you want to go?".
* As the user types in his destination / search, the website immediately responds informatively and aesthetically.
* Once you have matched a destination, the background of the page changes to a beautiful image of that location, the vacation doesn't start once you get off the plane, it starts now. Going from plain white bkgd to a destination image bkgd ideally will slowly start to pull your user into a vacation mind set.
* Once you have matched a destination, the text on the homepage changes from "Where do you want to go?" to "When? You could type next week, or 03/22".
* If the user deleted the destination before entering "When", repopulate the input field with both the destination and when they want to travel text, he will now understand that you just keep entering information into the field as if you are talking to a person, or searching on google.
* Once you have matched when, introduce new imagery of activities you can do there and/or native food dishes. You are continuing the theme of providing your user with an vacation experience now, not later.
* Once you have matched when, the text on the homepage changes from "When? You could type next week, or 03/22" to "For how long? You could type a few days, or a weekend"
* After you have all needed search data, proceed to results, and if possible continue vacation now theme
* The search box should still work as originally intended as well.
Keep up the good fight, don't let them leave the home page without thinking "This is cool!", and I would love to one day hear people say "I need to adioso!"