Awww, that sounds really sweet. I think it’s a great idea, but I don’t think it’s a great idea to carry around a ring that valuable because there’s a chance that you or she could lose it and a ring that nice could also make you a target for theft. Maybe you could get an inexpensive ring to stand in as the engagement ring until you get home. That way you and she don’t have to be overly concerned about an expensive ring while backpacking.

I asked my girlfriend to marry me last summer in Venice — she loved it.   I made sure to do it on the first night so I wasn’t carrying an expensive ring all over the place.  I put the ring in my carry on and prayed that it wouldn’t get searched.  Good luck, and bring us back some stories!

If you take it, get insurance.

As for locations, the cheesiest (though still a good one if she’s never been there) would be the Eiffel Tower. There are plenty of places in Paris that would work though. Personally, I think Cinque Terre is more naturally scenic and would be a good choice.

I did the same thing with a ring around the same price.  We arrived in the morning and dropped our bags off at the hostel in one of the rooms.  The ring was in my carry-on and I didn’t have an opportunity to get it out without her seeing, so I asked the host if our stuff would be safe.  She said sure, it’s not like you have any gold or diamonds in there.  I made an excuse to go into my bag and transferred it to my money belt, where I kept it for about two weeks.

It turned out fine, but it was always on my mind.  Trying to keep it hidden, checking to make sure I still had it, worrying about it getting stolen, all on top of finding the right spot and words to make it as special as possible.  If you’re prone to losing things then I’d agree with the previous suggestion to bring a substitute ring, or ask her early into the trip to reduce the chances of losing it or her finding it.

I asked her when we were on a hike above Interlaken, by far the most romantic thing I’ve ever done.  I recommend someplace scenic or personal to her, like in front of her favorite building or painting.  I haven’t been to many of the places you mentioned, but from what I’ve heard I would go with Paris or Cinque Terre.

I’m another guy who’s done this.  Like delfrio said, get it insured before you go.  Go to any insurance agent and get a personal articles policy – it should run somewhere between $100 and $200 to insure the ring for a year.  I wouldn’t overplan your proposal; just wait for the right moment.  

congrats
 
Just keep the ring with your passport, don’t put it with your checked luggage and you’ll be safe. 

Wow, who knew there were so many romantic guys?! Congratulations Stellar—and to everyone.
A friend of ours did the same thing, he asked his girlfriend on a hike at the Cinque Terre.
He said he kept the ring in his carryon, and asked his girlfriend as soon as he possibly could.

Leave the ring at home, and bring one of those plastic ones from the Cracker Jack boxes, and propose with that. If she says yes, you know you have a keeper [] (plus you won’t be out $5,000 when you get beat up by gypsies in Rome [])

I agree with others that it’s best to leave the ring at home, especially if it has a sentimental value. Even if you propose to her right away so you don’t have it, she’ll be wearing it which makes her a target for theft, since it sounds like it’s a very nice ring. Replacing your travelers checks or credit cards is one thing. Replacing a valuable piece of jewelry that already has a sentimental value and will have even more after you propose is something entirely different. Either wait or get some type of cute stand in ring.

The concerns about theft are being blown way out of proportion here. 

Maybe so, but it’s still “better safe than sorry.” Even accidentally losing it there would completely destroy your trip.

Bring it along and propose – it sounds like a really romantic idea. I had the same idea and didn’t follow through and always regretted it!

As far as concerns with theft, they are relatively absurd. My wife always travels with her “engagement” ring, even to places like Cambodia and we’ve never had issues. Most married people tend to wear them while travelling! You can call your insurance agent BEFORE going though and add on a “personal articles policy” (AND YOU SHOULD DO THIS) and then you’re totally protected!

If I were the guy with the ring, I would be less worried about theft, and more worried about misplacing it.

The same people who worry about ring theft are the same lot who are afraid of having their ultra-sharpe linebeard stolen while on the road.  I urge you NOT to shave your linebeard before your trip, chances are that nobody will shishkatook or decomish the linebeard out of jealousy or hatred, but will respect the shit out of it.

What a lucky girl!  Insure the ring, bring it along. 
 
I agree with Cinque Terre.  However, I just got back from Europe and decided that it would be so romantic to have someone propose to you in Florence on top of the Piazza di Michelangelo as the sun is setting.  The only thing is that there are other people up there but it’s such a romantic place! 
 
Good luck!