I just paid off a huge chunk of debt which will free up a fair amount of cash going forward. So, I want to save up and take a trip! Somewhere! Where I fly over an ocean! Other than parts of the U.S., and Vancouver, B.C., I've never been anywhere. Europe, Africa, South America, Asia, Australia, I'm open to it all. I currently live in L.A. but grew up just outside Boston. Here are my considerations:

Already traveled to: Driven cross country twice. As well as have seen parts of the East, South, West, Pacific NorthWest of the U.S. and the aforementioned Vancouver, B.C. That's it. Length: I have a ton of vacation time coming to me, 6 1/2 weeks! (I never take time off.) Realistically though, my boss would never approve all that (I asked…), but 2 1/2 to 3 weeks, with enough notice is doable. Ideally, I'd love a full 2-2 1/2 weeks for travel, with a day or two at the beginning/end for prep/decompression. Budget: Already have $524.70 in the travel fund! I'm looking at around $6000, total, saved in 3 phases. I should have $2000, by the end of the year, another $2000, from my tax return in January, and the final $2000, by the time I would want to leave. I could probably scrape together another $500-$1000, if needed, too. Climate: Not really a beach guy. I don’t hate it, necessarily, I just don't seek it out either. Plus, I live less than 10 miles from one. I don't mind rain/snow/cold, but that being said, I don’t want to spend 2 weeks in galoshes and rain gear. Other than that, I'm pretty open to whatever. Food: Ok, so, cards on the table, I am a picky as fuck eater. I may be 38-years-old, but I pretty much eat like a 12-year-old. That being said, I'm not looking to stick to familiar, shitty chain restaurants. I would like to be somewhat more adventurous, explore the local cuisine, but know myself well enough to know I'm not going to eat something I can't identify. And, I do have a bit of a sensitive stomach (yeah, I'm a wuss), so food needs to be on the milder side. I enjoy a nice cocktail now and again too. Outdoors: I'm on the bigger side, but I do run and hike fairly regularly. So I'd be up for a bit of adventure. But I'm thinking this trip should be predominantly relaxation/exploration with the occasional active excursion, rather than a solid 2-week trek up Everest. Culture: This is the point, right? The whole reason to go. I'm a sheltered white guy from Massachusetts. This will be my first ever international trip. But, I'm not looking to immerse myself in the jungles of Papua New Guinea and get off the grid for 2 weeks. I do want to get away from the screens a bit though and break out of my comfort zone, at least somewhat to start. If I can't do that then why go at all? Safety: This is my big concern. I'm a smart guy, slightly paranoid, but, other than my 2nd drive cross country, I've never traveled alone (as I probably will be for this trip) for more than a day or two. What should I be legit concerned about?

I signed up for Groupon Getaways and Living Social Escapes to keep on the lookout for deals. Has anyone had background with either? Would you recommend booking through either of them, or just go it on my own? I checked the FAQ and sidebar, which are great resources. I’m just looking for additional ideas/tips from travelers, especially first time, solo ones like I soon hope to be… Thanks!