As an eldest child, I was always expected to look after my siblings, and whilst I would feel awkward asking for the lavatory for myself, had no problem of politely asking, My sister needs the lavatory, where is it please? etc etc., That actually was a good way to begin being the one who sorted things.
So I have lived abroad, moved on my own and with other people and am perfectly happy to go wherever I want, with no worries about eating alone in a pub or cafe or whatever. Obviously you take sensible precautions about things like walking down dark alleys or whatever, but other than that I just go to whichever takes my fancy. My money is as good as anyone elses and I expect to be served and treated like anyone else. So if someone tries to put me in a dark corner or next to the toilets or whatever, I simply look round and choose the place I want to sit at and sit down there. I do not choose large tables stopping a bigger party, but something that suits me. I have never had any problems, enjoyed doing things at the times that I want to. If you walk around , expecting things to be ok, they usually are, because your body language also shows that you are just part of the rest of the people walking around.
I have always been happy to drive anywhere, and have done over 10 years as a hospital car driver. So recently there were two ladies who used to be able to drive , but now no longer are able to do so, and were saying how much they miss being able to go anywhere not on the bus route. So I offered to take them to the coast, I would pick them up at their homes and we would go to the coast, then we would do our own thing and meet up at 3.30pm to come home. One lady started to say oh we could go to the shops together - and I immediately said "No , that is not what I am offering. I have no interest in shopping and will be looking out to sea etc., As I have offered to take you , I will still do so this time, but I would be very unlikely to do another trip. This way we get a day to do our own thing and then I would be happy to repeat this. " She obviously was a bit shocked, but then agreed to what I offered and in fact we have done two trips since then . They all thought it was a bit "plain speaking", but after the first trip, each of them said it had been very nice to actually have a day to please themselves, which was quite rare.
So although it can sound rather bossy, I have found that being honest and telling the truth, can often mean that the other person can also be truthful. So I went on a trip to Barcelona with a neighbour, where we agreed to just go together as it was cheaper and a better room to share. Then we would do our own thing and might or might not meet up for a meal or coffee. It all went off very well, we did our own thing, met for one meal and one coffee, and it saved us a lot of money .
Even if it is quite hard to state your preferences in the beginning, if you look at it you will see that you will have to constantly dampen down frustrations , or find yourself having occasions spoilt by ending up doing what you dont want or like to do. This in turn will probably stop you having more trips.
So you could have a think about when you would prefer to be on your own, and you can have polite ways worked out to tell them, so for example you could say " I prefer to travel alone to this class, but we could meet later for coffee if you would like" You could practise in simple ways, starting by perhaps going by bus into the town or city, have a wander round, choose somewhere that appeals and go for coffee or a meal there. Another easy way is to see if there is an exhibition, or an art gallery with something you would like to see and go to that. They usually have cafes there, so that you could try going there after your visit.
I have a lot of friends, but still prefer to travel alone and went up to the arctic with Fred Olsen, have been back on my own to Portugal and Maderia where I used to live, gone b@b to lots of different places, whenever I wanted to travel to somewhere new. Have never regretted it. I am sure we have all done our fair share of looking after family and fitting in with other peoples needs. So now is the time to do as you please. Go for it. Happy travelling