I was there a couple of years ago and had a great time walking the different neighborhoods. I highly recommend going to Senhor Vinho to hear great Fado music... your hotel can make a reservation for you. Bairro Alto and Rato are the principal gay areas. Nightlife in Lisbon is fun, but plan on taking a nap before going out, since most nightlife starts VERY late by our standards. Most clubs get started around 2am. As a result, most stores and restaurants don't open until 11am. The Cascais (coastal area) is an easy day trip by train, but it was a bit too touristy for my taste. The public transportation in Lisbon is great and fun. Hope that helps and have fun!