You have a tough decision to make!
If I were in your position, I'd consider cities or specific sights I'd like to see. Also, the budget is an important factor. Is this going to be a mustachian vacation?
Cheap ideas:
- Spend a few days in a new city:
I did a 2 night trip to Chicago a few months ago with my wife, and we had a lot of fun, and saw a lot of museums, only spending about $200 total. (Had free hotel rooms through IHG rewards).
- Visit friends/family:
If you have people you don't see often enough. Whenever I have a free weekend, I try to drive the ~2hrs to the city where a lot of family and friends still live.
- Travel to see a Show:
If there is a band you love, and they're playing a city you want to visit, you can knock out two birds with one stone (or money-wad).
Expensive ideas:
- Iceland:
I want to go to Iceland, and my wife doesn't. It's a priority for me, even if I have to go alone.
- Tokyo:
You can get a ticket to Tokyo for ~$1000, iirc. It's pretty English friendly to navigate the Yamanote line, and you can ask just about anyone on the street, or train, for directions. Many Japanese are happy to give you suggestions for where to go, and like to practice their English with you.
Lazy idea:
- Day drink, and binge watch all of the shows.
Whatever you choose, have fun!