No trip to P-town is complete without a stroll down MacMillan Wharf, the heart of downtown and a historical site all its own. Still a working pier, MacMillan was built in the 1800s and retains much of the charm of the seafaring life. It's also home to several water-borne adventures like Cee Jay Fishing and Dolphin Fleet Whale Watch.
With the sun about ready to set, it's time to head back into town for happy hour at Old Colony Tap, a dive bar popular with local fishermen where it's still possible to find a cheap beer and some good-time jukebox jams. Or head to Pied Bar, a lesbian landmark with no cover, strong drinks and an easygoing deck scene with views of the water.
After hanging with the locals for a bit, walk over to the East Side of town for the free Gallery Walk that takes place every Friday night in the summer season. Local galleries throw open their doors to the public, often serving small bites and glasses of wine. It's a great introduction to the artistic heritage of the area and will help you learn your way around.
Before heading back for some sleep, grab dinner at the Portuguese Bakery, an old-school storefront that's open morning to night selling pastries, sandwiches, soups and sausages just like Grandma used to make. The prices are among the lowest in town, and its close to the bus stop that will take you back to the hostel.