FTFF

UPS:

What do I do to entertain myself during free time:

Exercise is my first layover priority, after sleep. Running is a great way to see a city in depth, it's easy and free so I do it a lot. I've hiked forests, mountains, etc., rented bikes and rode 3+ hours (e.g. along Rhine), surfed/Sup in Hawaii and Sydney, I'll swim whenever a pool is available, and though I've not done it yet, guys will ski/snowboard. A lot of times I'll go for long walks (3+ hrs).

I like to eat good so part of my time is trying new places and new foods especially internationally. Obviously going out for beers is popular too.

Otherwise the world is your oyster. I've gone go kart racing, golfing, taken in concerts (U2), seen euro futbol games. I've flown with guys who scuba dive, skydive, kitesurf, fly gliders, race cars, shoot guns, one guy brought his guitar and did a few open mics, another guy does standup comedy. On the longer overnights guys will sometimes travel, especially renting a car and doing a road trip (Normandy). One guy writes music on his laptop, another brings his Xbox so he can play with his kids online. I've flown with one tennis nut. A few people have side-businesses, day trade, or do union work. Internationally a lot of guys will get massages (real ones). I'll hit the beach or pool and chill in the warmer months. I'll also get work done: study for recurrent, bid, contribute to these forums, etc.

Do I feel like I’m married to a hotel room?

I did a little bit at the regionals, not at UPS. Why? Probably better hotels in better locations and more disposable income to enjoy the layovers.

Do I feel like most of my time is spent at a hotel property?

Regionals: yes.
UPS: No. But, some of the domestic night flying can feel that way a bit - eat and sleep.

How much time do I explore the city?

Regional: Occasionally.
Corporate: "Most of the time. Although, we go to a lot of the same places, so we get bored with many of the towns." I don't get bored as much as I fall into a routine.

Do I frequently hang out with the other crew members?

Depends on the schedule of the trip and the people I'm flying with. Sometimes it's nonstop, other times we all slam-click for most of the trip. I've had good luck bumping into friends all over the world.

Flip side of things:

Admittedly, sometimes I'm too tired to do anything and will barely leave the room, if at all. Sometimes I wake up from 8hrs of sleep and it's 1am - not much to do and some cities you don't really want to go roaming around at those hours of the night. In that case I'll hit the gym or spa if it's 24hrs, read, Netflix, etc. Crappy weather = internet surfing, museums...