It never hurts to ask - my husband and I often travel for work and usually travel alone. It can be really hard to both get time off at once. And then the idea of paying for a hotelto take a weekend away just for us is rather wasteful, or a bit of hassle to use other options.
Meanwhile out work often books us into nice hotels when one of us is away. So we thought of seeing if one can "tag along" when the other travels and at least have the travel time and evenings together.
A month ago I had a speaking engagement out of town - they offered to pay my spouse's meals too if they wanted to come. So we had a nice drive, hotel stay, and meals - all covered plus what I made. It was on his off day so he didn't lose work time. Total work time on that trip was 3 hours and the rest together.
This week he had to travel for a work certification, and while I had to pay for my own meals, they were fine with me coming along and staying in his hotel. I had an extra day off banked from working the Thanksgiving weekend, so I used that. He was at the certification for 7 hours and the rest of the trip was us/travel.
So we've had two nice two-day trips together with the only cost being a couple meals!
I really really regret that pre-kid, I was such a stupid workaholic that I never did this. My husband traveled fairly frequently -DC, Florida the main examples. His boss offered to let me tag along for the price of the flight. His wife went with him. I never did. Dummy.
I used to live in DC and still have many friends there.
Once, post first kid, my spouse had back-to-back trips to DC when he was supposed to arrive home midnight Friday night and leave at 6 am Sunday morning. So he just stayed for 1.5 weeks. We used miles for my 5 year old and I to fly out for a 4 day weekend. It was pretty awesome. The only stress was getting to sit together with the last minute flight. Oh, and he asked questions from the minute we got to the airport, through the first short flight, the layover, and an hour into the second flight (so, about 5 hours straight), until I held his little face in my hands and said "stop asking questions and go to sleep!" It was 11:30 pm, and he put his head on my lap and was out.
We enjoyed a weekend in DC - stayed with friends in the area and their kids, saw other old friends, did some sightseeing. It was great.