Bruges is my home town.

The only hotels in town I have experience with are the Orangerie, de Tuilerieen, Flanders Hotel. There's a variety of other hotels available so if you have questions, let me know.

Food-wise, a lot of places want reservations. You may walk into a place and see empty tables but they may refuse service if you don't have a table reserved.

My favorite place in town grills their food and is off the beaten path. It is called Bistro De Schaar. The food is fresh and absolutely delicious. http://www.bistrodeschaar.be/de-schaar/home.html. If you want a place that's open late, try http://www.christophe-brugge.be

You should try the fries while you are there, but I do not recommend the places by the Belfry - simply not good and expensive. For fries, I'd go to Chez Vincent - by the St-Salvator Church. Pickels in de St-Jacobsstraat - close to the market square has been around for a long time too.

If you want to have a beer, 't Klein Venetie bij de Rozenhoedkaai may not have the largest selection, but it's right in front of the most photographed spot in town.
If you want a good glass of wine, and some high quality cheeses or charcuterie to munch on, go to the Cuvee. It's a 4 minute walk from the market square: http://www.cuvee.be
If you want a place that has a nice selection of beers, of which some are really rare, I suggest Rose Red (has a hotel attached to it):http://www.cordoeanier.be/en/rosered.php

Let me know if you have specific questions or interests and I will do my best to help you.