Olde City, Philadelphia
Great place with bartenders who know what they're doing and don't keep you waiting. On Friday and Saturday nights you can find yourself 10 deep at the bar. Crowd ranges in age - but weekends are typically 20's to late 30's. Sundays the have a tasty Brunch Menu. At 430pm on Sunday's the Irish musicians play for a few hours.
Tool around olde city to a number of bars working your way from the Plough up to Cuba Libre (and St), Olde City Conti (2nd St) turning left onto Market and hit Drinkers (div bar) for a quick change of pace the down 3rd Street into a Bar Named Sue and back around to Chestnut Street hitting Paradigm and Amada.. cross 2nd Street and hit Eulogy and the Mexican Post or Brazils and then left up Front Street to Swanky Bubbles and Warm Daddy's... so many bars, so little time...
Dress Code: Casual to trendy
There are tons of smaller clubs and bars in old(e) city just take a walk around and find what you like. If you are looking for live music or DJ's it's all there. The prices are comparitive to other clubs, so yeah, bring the plastic.
If you're hungry the Continental at 2nd and Market is a great diner-type place for cocktails and food, it's smack in the middle of everything and not that badly priced!
South Street, for all it's great reputation is really not all that great. The shops close early, it gets a really "young" crowd and is just better suited for a day thing, but that's just my opinion.
In the summer the parks usually have festivals and music and some of the restaurants even have outside seating available -- do take advantage of that.
Carriage rides at night at really romantic, guys bring the wine and the wallet cos it's about $ 20 for a 6 block ride, but it's a sure mood setter.
Weekends are the best time but the weekends here seem to start on Wednesday night and last until Sunday, every night has something different to offer however and I've never had a truely bad time. Well . . .
Dress Code: Now I'm going to say be yourself. Common sense sould tell you what will be acceptable at the places you go -- obviously ripped jeans and flip-flops are not going to fly at an upscale place. but if that's what you plan on wearing, you're probably not planning on the upscale places!
Really who tells anyone what to wear!