I visit Skegness every summer, and it is quite a good town for pubs and bars. The area has recently been devastated by two fires, but there are still plenty of places to go to.
Marine Boathouse is one of the top bars in Skegness. It's open every day and night, and hosts live bands on some weeknights and has it's own DJ at the weekend. I have quite often been in there and been unable to move easily due to it being so busy. A lovely restaurant is also based upstairs in Marine Boathouse.
Litten Tree is great at the weekends, with a good party atmosphere. Wolfies is another great bar that has it's own DJ playing a great selection of tunes. Other good bars include The Gallery (down the highstreet), The Water Hole, Barlife and Harveys.
If you like to party until the early hours, the best place to finish up in Skegness is LA Cafe. This is a very good nightclub based upstairs near to the clock tower. They sell loads of cocktails and play a wide variation of tunes. It also has a good dancefloor.
Situated immediately across the road from Skegness Pier is one of the towns friendliest 'Pop Pubs'. The Barfly is part of the same stable as the notorious Club Rhino, but don't let that put you off. The staff are cheerful and friendly - and even the doorstaff seem less menacing than most that you come across! There is a small dancefloor, which, on the occasions that I have visited, seemed full most of the evening, the dj being happy to play any request that was in his power. Unlike many of these places, the music is set at a level which, whilst still quite loud, is perfectly comfortable to talk over (I believe this is something to do with the quality of the sound system). Drinks are sensibly priced - and food is available during the day. I would recommend Barfly as part of any pub crawl around the town, but if you make it you first stop, you may just find yourself spending the whole evening there!