I've been a solo traveler for quite a while and I certainly prefer it. I remember being stunned when I did weekend trips with friends during my 20s and they'd sleep until noon, then lay around in their underwear and watch trash tv until it was time for happy hour. Or, they'd want to go see the same movie we could see back home rather than do things unique to the city. As I got older, I had travel companions who annoyed me in different ways. I had one who wanted to 'browse and wander' Now, I've certainly spent time walking around interesting neighborhoods and stopping in for a coffee or a beer, but I need some structure. On the opposite extreme, I had a friend visit Chicago who had an extreme touring plan carried out with military precision.
Solo dining isn't that awkward for me, but I'm not a die hard foodie so I'm not seeking out Michelin stars. I'm comfortable in a cafe, bistro, or a pub.
It is annoying that you don't get to split the costs of a hotel room, but traveling solo allows me to take advantage of some of the very small hotel rooms that would only be acceptable to a very close couple traveling together. Those glass partition bathrooms can be a deal breaker for all but the closest of couples.
it is nice to be able to set your own pace. You're not stuck wasting time in a gift shop while your companion looks at endless tacky tourist souvenirs without buying anything. You have complete control to decide to skip an item on your agenda if your legs are just too tired and you'd rather watch a local sporting event at a pub .
The above post is absolutely correct, there is no one right way to travel. A great friend of mine will only do all inclusive resorts. That would bore me to tears, but I know she'd be scared of her own shadow even in London and worried that Jack the Ripper was lurking around the corner in Trafalgar Square. I had a coworker that mocked me for my habit of arriving extra early at the airport. I'd rather pay for the overpriced airport beer than be one of the cool kids and running to catch my flight, taking my belt and shoes off as I attempt to set a world record in the 100 meter dash! I admire a lot about Rick Steves, but I'll never travel carry on only unless it's a domestic weekend trip to a warm weather destination. My backpacking days are well behind me, I do pack light, but I'm well prepared to do laundry or have it done for me on a trip longer than a week. There's no way on earth I'm going to wash clothes in my hotel room. i bring jeans most of the time unless it is a hot climate or I know I'll need something dressier.
There truly is no one way to travel. But, if I ever travel with a companion again, there will certainly be discussions beforehand about expectations. The last thing I need is another 'free spirit' who thinks I'm being anal by always taking the hotel's business card with me. I do that so I can always hop in a cab and get back to the hotel. That's the same reason I always take a picture of the hotel room number. I don't need any more late night drunken texts from a companion asking me what the name of the hotel is or where the room is.