Ok so I'm thinking I need pages for
Hotels
Guest houses
What's On
Cinema
Galleries and museums
Beaches
Shopping
Get here
Contact
I think having a what's on makes it a lot more 'hands on' than not to keep it updated. Take a look at Wrexham.com. The last going out post on the homepage was 'Bonfire night events 2011' and imo does the site more harm than good as is doesn't look like it's being kept on top of, and keeping on top of them takes time, or money.
Also, looking at your list you have hotels and guest houses first, which is probably your priority. My priority would be local information, history, the area, local knowledge, local quirky independent shops. Make a really interesting site, full of pictures, doing this will make it really easy to get quality links from similar sites but also from hotels and guesthouses as it's quality information they can refer their guests to.
You can also feature any interesting/old/different hotels/buildings/attractions, get some interesting facts/pictures/stories, write it all up then ask the owner to link to their feature from their website. (The benefit of this is you get free content, a link and a high ranking when someone searches for their hotel/business name)
Once you have all this I would then look at monetising it with the guesthouse/hotel stuff. It is a lot more work and takes longer but you'll get a lot better result than installing wordpress, sticking up lateroom banners and a hotel datafeed and then wondering where to go next.
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