Bound by Seventh street to the west and Front street to the east (read: the closest you can get to the Delaware without falling in), Old City runs the cultural gamut between a vibrant nightlife scene and a highly revered cultural upbringing. Arguably one of the most historically rich neighborhoods in Philadelphia, the relatively small area south of Callowhill is home to touristy heavy-hitters such as Elfreth's Alley, the Constitution Center and Independence Hall. Be sure to take a stroll around the area during the first Friday of every month when the area's art galleries, restaurants, late-night hot spots and one-of-a-kind boutiques open their doors for some after-five relief in the form of free drinks, live music and discounted parking.
With literally hundreds of area restaurants to choose from, you'd be hard-pressed to find a block that doesn't contain at least one need-to-know eatery. For starters, be sure to try Jose Garces' award-winning tapas bar, Amada (perfect for lunching with clients), or Starr's Asian Fusion hot spot Buddakan. If you're still hungry, head to Crocodile Bar for their ridiculously delicious pickleback shots (and free pizza) or the locally-based Triumph Brewery, where Philly's solid canon of microbrews presents itself on a larger-than-life chalkboard behind the bar. Be warned: the area around Chestnut and Second is a weekend breeding ground for young, out-of-town drinkers stumbling around to spots like Buffalo Billiards, late-night 32 Degrees, champagne-heavy Swanky Bubbles and dives like Rotten Ralph's. Locals and more refunded drinkers usually can be found at Eulogy for Belgian fries and a novella-sized beer list, Haru for sushi or the BYOs north of Market.
Introduce your out-of-town relatives to your stomping grounds with a little help from DeTours Segway Tours; after all, the 'hood boasts a solid theatrical past, as a setting for which both Rocky II and National Treasure were based. Afterwards, make your way down Third street for a much-needed brunch at Farmicia, where Philly's farm-to-fork trend spawns a rotating menu of delicious, seasonally-based ingredients. Other favorites include Azalea Restaurant in the Omni (good for impressing your mother-in-law) or National Mechanics, where the eggs benedict will cure even the nastiest of hangovers. When it gets warmer, you can trek over Dock Street to Penn's Landing and the trails along the river. Check out the boats being carved at the Independence Seaport Museum and then have a drink on Keating's patio and watch the sailboats dock right in front of you.