Cocktail hour or not, theme week or otherwise, P-town needs no special reason to drink. There are 25 places for cocktails, good and not-so-much. In fact, there are probably more like 100 watering holes but I’ve never counted and after a few rounds.... well, who cares. Here then is my short list of favorites for a multitude of reasons. Because sometimes you want to be trashy with strangers.... and sometimes not. 

Harbor Lounge at 359 Commercial Street is where we return time and again. A sweet mix of daily special cocktails (and always the signature spiked blueberry lemonade), comfy indoor seating, a deck that juts out into the harbor like a jetty and nearly guaranteed conversation with people who began as strangers. 5p.m. to 7p.m. is its sweet spot for the view of shimmering water on the harbor. No cover charge. 

The bar at The Red Inn at 15 Commercial Street would be good enough but it’s claim-to-fame lies outside its doors on the beautiful deck. At the east end of the deck are the coveted lounge chairs, good enough to either rock yourself into a snooze or chat with strangers. If you’re having a meal at the inn, arrive early to soak in the view. No cover charge. 

Tea dance at Boatslip at 161 Commercial Street is in a class by itself. Here, you and 500 of your closest friends can get crazy. Pay no attention to the mediocre drinks that they’re serving. Stay long enough and you’re sure to meet quite a crew, some of which may include your own friends, the people you sat next to at dinner last night, guys dressed only in Speedos, 6’6” drag queens and so much more. It may be the longest running show in town. Opens at 4p.m. and closes at 7p.m. sharp. $10 cover charge.
FYI...the Buoy Bar out front offers admission without cover but is definitely "Boatslip-light".

Shipwreck Lounge at 10 Carver Street in the Brass Key Guesthouse is interesting if only for its sheer variety of outdoor seating options……. the pods, the sectional sofas, the seats around the fire pit and the stand and lean columns. The drinks are a cut above most bars and the staff pleasant. Perhaps a bit of a yawner but perfect for your last stop of the night. No cover charge. 

Although not among those I have been to frequently, town favorites also seem to include The Monkey Bar (especially during Bear Week and with the benefit of being able to eat a meal there as well), Gifford House (with its considerably younger crowd), Aqua Bar (also with a good food option), and the A-House (with its theme nights and dance floor).