Hi - first time poster here. I have an unusual travel plan and am curious if anyone can recommend the best way to book flights for it.

I have a list of 8-10 cities each within a 3-hr direct flight radius from NYC, where I live. I want to visit each for a weekend, Fri PM to Sun PM, sometime over the next six months. I'm indifferent about which weekends exactly and which order. Any NYC airport is ok, but it does have to be a direct flight both ways, or it isn't worth the time.

Is there a way to set up a flight alert this complex? For example, Kayak has a "weekends" search option but only 4-5 weekends at a time, and then the alert option seems to be focused on just one of them.

Also, is it worth focusing on a single airline or miles program? I currently have no status or significant mileage accumulated with any one airline. I also travel for business maybe once every two months, usually longer trips. I'm open to flight/hotel packages and not committed to any one hotel system.

Any other advice is appreciated!

Short answer: No
You either have to search it yourself manually or pay someone to do it for you, there are several conciege websites out there.