I spent the last few years in the same situation. Southwest Companion pass, lots of SW points, and plenty of hotel points. I decided to do a lot of 3-4 night long weekend getaways.
I chose to stick to "cheaper" locations to maximize the number of trips. We also got used to flying with one stop. Just took a bit more time but no biggie.
For weekend trips, driving more than 2 hours was out of the question though. That nixed a lot of cool places for us
These were some of my faves:
- Orlando of course. We ended up with annual passes to Universal and went 3 times.
- Denver. The mountains are sooooo close. We stayed the first night near the airport to acclimatize then moved to a rustic cabin in the mountains. LOVED it soo much!
- California. I was shocked that prices were actually reasonable to fly so far. Not that much different from flying to Orlando. We flew in to Burbank, drove around for a week, then spent a week in DLR, flying out of Ontario I think. Long flight now, and not direct.
- Vegas. SW had nonstop flights here. We are not gamblers so soon started finding other things to do. Discovered awesome hiking pretty close to the Strip. And of course, the weather is great in Vegas in spring and fall. We went 3 times.
- Washington DC. BWI is super cheap to fly to, hotels are reasonable (we often stayed in Arlington) and museums are free. So cheap weekends!
- Providence, RI. Flew here for work and DH came with me. Not bad, but too many people for me. Unfortunately we had to nix Boston due to a major flight delay.
- Phoenix. We loved the hiking. Sedona was majorly cool but very few chain hotels. Phoenix had tons of Orlando - style resort properties though and we were thoroughly spoiled with an upgrade to giant Suite at a Hilton resort property. Amazing place. Great place to stay on hotel points. Didn't like how brown Phoenix is though.
- Nashville. I loved Nashville. Huge hit with this country fan. It was safe, clean, and the bar scene was tons of fun (I don't usually like the bar scene). Love that it was casual with no cover charges.
- Austin. Spent Christmas week with the kids here. It was pretty cool. We had a blast checking out all the Crazy Christmas lights everywhere. Every night, we would drive to hunt down Great Christmas Light Fight - type houses. LOVED it. Also had fun trying out insane amounts of Texas BBQ. DD loved the laid back horseriding we found here. (I was shocked at prices myself but eventually found a cool ranch with low prices). We then drove to San Antonio - the riverwalk they have there is really pretty but their NYe party was a bit of a letdown.
That's all I can think of for now
We're out of points now...it was super fun while it lasted!