Some bar meals may be a great way for you to break the ice on a solo vacation (I haven't tried them) but definitely book at least a few fun tabletop reservations for yourself. I've eaten on my own countless times and never felt out of place. The reality is that most families or couples around me are so into their own issues and dramas that they never look up to see me at the next table dining alone. I've never felt awkward or that I stand out. I enjoy the ambiance of the restaurant and sometimes do chat with folks at the next table if the situation works that way. Some solo diners use some of the more awkward "waiting for food" time to check their itineraries on their phone, post text msgs or emails. I people watch & just enjoy the restaurant. I also really enjoy a bit of elbow room and quiet after being surrounded by people for hours in a busy park. A couple of good starter restaurants for dining solo are San Angel and Sci-Fi (some people are more comfortable in a darker atmosphere since they feel they are not as visible) and buffets like Boma, Cape May, Tusker House & Biergarten (putting in your time getting up for food). Personally, I just make reservations for a mix of tabletop reservations that I want to try or are old favourites . . . regardless of the "I'm eating on my own" thing. On a very few, rare occasions, I've had less than great service because of the assumption that the tip isn't going to be as good with one diner, but it doesn't happen often. Do branch out from bar meals and try some tabletop. You may be surprised how easy and comfortable it is!