Provincetown is great. Best times depends what you are looking for. Busiest weeks are Carnival and Bear week. Also most expensive and hard to get a room. I'd avoid Family week and Women's week (given your stated interests). My favorite time is off season (esp. after Labor Day), but I prefer quieter times. The "shoulder seasons" are still quite busy and easier/cheaper rentals. The "heyday" of public sex at "Dick Dock", The Dunes and bars have largely gone the way of gay marriage and the internet, like the rest of gay culture. There's still plenty of sex going on, but the place(s) to hookup are mostly online. The "magic" of Provincetown is it's almost 100% gay, beautiful/quaint New England seaside village, and it's really compact/walkable. It's also quite expensive; which limits the clientele to affluent men and party boys working 4 jobs to pay the rent (this can be seen as a positive and negative). There are fantastic restaurants, beaches, and a handlful of bars. New Years Eve is a great time to visit. Most B&Bs have a 3-5 night minimum "in season". My favorite guest house in PTown is the Carpe Diem (fab rooms, clothing optional courtyard and beautiful spa). The Bear and Leather events are the most "sexually open". Here's a list of all the "theme weeks": https://ptownevents.com/provincetown-theme-weeks/ Provincetown is where I learned at the age of 19 that there is a big varied gay world out there, and I set my sights on getting out of my small home town....have been in Boston now since age 23. PS "in season" you might find a few (visiting) 'scorts there, very few off season. Good luck!