Don't beat this newbie up. This is my first time redeeming hotel points for a free room! I've got the airline part down pretty good - 2 round trip tickets on Southwest from SAN to MSY during the busy thanksgiving travel season for just $22 in taxes and fees and 30,000 RR points.

I'm going to New Orleans for Thanksgiving, no family, just 4 days and 5 nights of leisure and fun away from it all with my partner. I'm figuring out which Marriott Hotel to stay at, and I have more questions then answers. I mean, the real me, wants to go big and stay at The Saint. I like those boutique, non-corporate looking places, but it's 140,000 points and I only have 82,000. Ahh.. 1st world problems. I could have him apply for a Marriott card or Ritz card and try to rush the spend in and combine points... BUT, we're technically not legally married, even though we live together and own a house together, so would Marriott allow us to combine points?

Alternatively, if my Chase UR points post before we travel I can book the hotel now and then transfer the points in when they post... But it seems to me like using a UR point for Marriott with such a low point value is a waste of the point.. Maybe not if it's creating a dream vacation, I just think I'd rather use those to stay in Hawaii or somewhere extravagant in Europe.

Lastly, there's always the option of staying outside of town for a few of the nights and only staying in the French Quarter area for some of the nights we are there. We aren't big partiers so it's not like we need to be able to stumble back to our hotel room drunk after reveling in the French Quarter. However, if we do that then we miss out on the 5th night free when redeeming awards.. but we can stay in a lovely little Courtyard in Materie for just 80,000 points. Then I could use my free cat4 certificate too, BUT it's a wash since the 5th night is free anyway I would negate that using the certificate.

What to do? Do we really want to be in downtown New Orleans the entire time anyway, or are there things to explore outside of the city that would make it worthwhile to stay in a lower category property? Or should I just double down and go for broke and do it?