I have always wanted to visit France or Italy and enjoy the food and wine and the culture. It wouldn't be fun alone, and I no longer have an S.O.  

You both would need to be certain you will be compatible for a long period of time.  

Make sure you can survive a long weekend together in the same room before committing to a longer time together. An overnighter is not necessarily a good test for a week or more together!

You might want to take a look at the link below.

Don't overthink it.  Just do it.  I guess the "risks" are the same as if you took a vacation with your girlfriend.  You or her could get sick, she could be tired from the jet-lag, maybe you'll disagree on some sites you'd like to see....

I'm always amazed when people makes this statements that they couldn't or wouldn't enjoy traveling alone.  I'm certainly not going to allow myself to sit idle on the sideline because "it's not fun going alone".  I've traveled all over on my own and have totally enjoyed it.

getting blown up by a crazy middle eastern guy.  Anything else is fixable.  

“I have found out that there ain’t no surer way to find out whether you like people or hate them than to travel with them.” – Mark Twain

As I said in an earlier post-take a weekend or a few days together in the United States-to test it further-do a Bed and Breakfast visit....

I've almost always traveled alone. For thirteen years, every July I did 5,000 to 7,000 mile motorcycle trips out west for two or three weeks by myself. Loved it.

Traveling on the spur of the moment usually necessitates traveling alone unless you have someone who can also leave on a moments notice, but just because you take the flight there alone doesn't mean for a second you have to spend your trip alone.

Sometimes they are just a spur of the moment thing, sometimes they are well planned out.   My next big adventure, which I've been planning for on and off, won't have me even remotely close to hotel.  

right in front of my beach front hotel room.  

Sometimes I'm very much in the mood to chill beach front somewhere and not move a muscle, other times I'm looking to get my adrenaline rush.  

I like to have an overnight before committing to a long trip just to be sure we are travel compatible. So much to consider, like sleeping habits, eating habits (I traveled once with someone who didn't like to eat) and the ease with which my travel companion navigates hotels and airports. I am not an anxious traveler. Being really compatible could effect your final bill in a positive way.

Actually, when I said that traveling alone is no fun, I really meant that doing the wine-and-cuisine thing in Europe is no fun if you have to dine alone. Table for one? Forget it.

it really should be the same as an IRL trip. It's not all about any one person. It should be about a great time  
for both people.  

Just like we no longer check out the ads in the yellow pages, or cruise the bad neighborhoods looking for SWs, finding a companion anywhere in the world in the 21st century is a breeze.

Great advice...and yes, all humans need some alone time to be their best.  I am fun, but not a toy.  Companionship is more than that afterall- touring, dining, fine conversations are all part of the trip too.  

Thanks, Gambler, but my VIP subscription expired. Maybe you post a clue or two.