Trip Planning Take 2

I think I've found myself the perfect travel companion, now I just have to figure out where to go.

I'll address the first part first. So back in April I met these a few people through a chatroom. One of whom you've already heard quite a bit about as our relationship has progressed through friend and more than friend to basically to mere acquaintance status and everything in between. The other I've mentioned briefly here (don't worry I'm sure you'll be hearing more about him in the future as well). As we talk more I feel like we're becoming closer and closer each day. And we've discussed things like places we've always wanted to visit. Turns out we enjoy many of the same things so finding something to do that we would both enjoy is really no problem.

Some of the places we've talked about going are Denver (roughly half the distance between the two of us), Boston, Nova Scotia, and Portland or Seattle. I've already looked into Nova Scotia a bit for myself, as you might remember. And today I took a look at Boston. After reviewing the tourism website, I have to say I want to go even more now.

Now all I have to do is convince my parents that this guy is on the level (which given how they reacted to the previous situation might be difficult) and that it's safe for me to travel with him.

Vacation Planning

I'm getting to that point in my life where I've got to start thinking about doing all of the things that I want to do in my life. I guess in someways I hoped to have someone to share that with and I'm getting kind of old to go on vacation with my parents, although I had a great time with them in Scotland last summer. So I'm starting to plan my first trip alone.

I've always wanted to go to the Fortress of Louisbourg in Nova Scotia. So I'm looking into that. But so far I've run into a couple of obstacles. Number one, there is next to nothing to do in Sydney and if I'm going to pay $500 round trip for a flight I want it to be a couple of days at least. Also anything I have found to do so far has been for couples or familys. And since I am neither a couple or a family that leaves me with nothing to do, except rent a car and go out to Louisbourg for a day. I was thinking I might be able to hit up a spa or something too. But that's all I've got.

Anyone ever been? Any ideas? Should I just wait until I have someone to go with or scrap the idea altogether?