Head to the Jupiter Hotel, centrally located on East Burnside and within easy reach of public transit to downtown, the North Portland gayborhood, and nearby southeast queer hangouts. Get settled and then it's time to head out.
First stop is the SE Portland neighborhood via the 75 line - this rapidly gentrifying area is great for shopping and was home to the city's only lesbian bar until it was forced to close its doors around 2010.
Grab a cup of coffee at Stumptown Coffee on Division, the citywide standard for coffee genius.
Wander down Division Street until you're hungry enough to grab brunch at the Waffle Window or a food cart pod, and hit up SheBop, the woman-owned and queer-positive sex toy store where you can stock up on everything you'll need for the night and beyond.
The next stop is the queer-friendly and clothing-optional Collins Beach on Sauvie Island. It's a hell of a cab ride but it's worth it - if not for the beach, which is a strip of sand along a beautiful but undramatic stretch of the Columbia River, then for the number of naked queers you'll find soaking up the sun.
If you're excited about a longer adventure, head out the Columbia Gorge to the gay male nude beach at Rooster Rock State Park, originally named "Cock Rock" because that's what it looks like.
Heading back into town on Route 30 from Sauvie, you're perfectly aligned to stop by Embers for a first drink for the night and to admire the fish tank that doubles as the bar. If you're into gay male spaces and drag shows, hang for a while. If a broader spectrum of LGBTQ folks is your thing, head out to NE Portland and settle in for dinner and drinks at the wildly popular and lesbian-owned Tin Shed.
From the Tin Shed, it's time to explore the wild LGBTQ nightlife of the North and NE neighborhoods. You'll have your pick of bars within easy reach of the network of TriMet buses, beginning right on Alberta with The Know and the Bye and Bye. Check the online PQ Monthly calendar for a schedule of queer dance parties and head to whatever's happening in North Portland that night - it's almost guaranteed to be packed.
When you need a break from the dance floor, start heading back to the East Burnside neighborhood, making sure to stop in at local partier hangout Javier's Tacos for cheap, delicious 24-hour Mexican food.
Back in the East Burnside neighborhood with food in your stomach, spend your second wind dancing at Holocene or having final drinks at Crush Bar. Last call is usually 2:30. Then it's time for a waltz down the eastbank esplanade along the river and a final collapse into bed.