We're getting close to being empty nesters/retirement and we believe this period of our lives will have a good deal of travel in it. Maybe one big trip or lots of small trips per year, we're open to just about everything. We've got a world map and a bunch of pushpins!

Reward/FF-wise, we are in discovery/accumulation mode - I'm learning the tricks of the CC/Points/Miles game but we're also open to discovering where in the world we want to go. We're not married to any CC ecosystem or FF program at this point; I have just over 100k United miles but no status. I just opened a Chase CC and will have 100,000 points there in a bit. Small amounts with hotels/airlines that aren't really worth mentioning at this point.

The issue I'm finding is that we'll have too much flexibility for seeing what's available. Literally everything is on the table - when, where, how long, how much.

Here's what I'm looking to do:

1. Find neat trips regardless of origin/destination - we're open to repositioning ahead of/after a trip
   1. I know about the Premium Fare Deals forum and will certainly keep an eye out there
2. Pick potential trips based on what shows as available at any given time - international, domestic, business, economy, etc.
   1. Think 'hey siri, where can I go in the next few weeks with a cheap business fare?"
   2. Essentially a search with an origin, but no set destination (maybe a region like E Europe?)
3. Not drive decisions on picking specific dates - we're going to be able to be ultra-flexible, so checking all available dates for a potential itinerary is soul-crushing.
4. Find tools to help me with the above

If a trip consists of an Origin, Destination, Departure, Return, it seems I need at least 3 of those for most search engines - I'd like to get it down to 2.

Any recommendations to get started with this? Handy sites that will help?

Thanks in advance!