Originally Posted by
standingoten
...I am coming out of Boston Logan (BOS).
I have:
50k Southwest RR Points
50k Amex MR Points
25k US Airway Miles
...
Can spend up to $2000 out of pocket as well.
Enough for an Atlantis Vacation.
But first affordable cruise does not happen until October.
With that budget you can go pretty much anywhere US...
Fort Lauderdale/Miami, San Diego/Los Angeles/Palm Springs (all three could be done in one trip), Seattle (in July-August, no rain, 9PM sunset) can be very gay and affordable.
San Francisco, New York, Chicago while great cities for a gay tourist, will come with expenses that rack up pretty quickly.
It will be EXTREMELY difficult to a find a low tier award anywhere Europe in the spring/summer at this point. I assume you want to go on a vacation right now, not in the winter when you will have forgotten about your ex

. If you pay for your air ticket, it will be at least $1000 from BOS which will eat up at least 50% of your budget. Your points are not enough for a full week hotel stay either in places like Barcelona, perhaps 3 nights in Berlin. So you will end up having to pay for hotels/ hostels. You will really blow up your budget in Europe. Really, Europe can't be done for too cheap.
Safe travels!