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Escorted Vacation or On your own?
DH and I are thinking we'd like to hit up Europe before we start having kids. I've been to Europe several times - he's never been.
Half of the times I've been to Europe, I've gone through escorted tours, which include a tour guide and a tour group that travel together for much of the vacation. The price of the tour includes transportation between cities, admissions to tours within the tours (of monuments, city walks, etc.) and usually some meals. I've liked these tours because you don't have to worry much about getting lost in a foreign country,and I always get to see more of the big things in a shorter time period because they keep the tours moving. There's also a feeling of safety because you have check-in times with your groups, an English speaking tour guide who's very familiar with the location, and the promise that you won't have to drive a car in a foreign country. 
I've also been to places on my own, and relied on travel guides to get me through. I really like the freedom to go where I want and to not be rushed. But I also feel like I didn't learn as much as I could have about the different places I saw other than what the guide books told me. I've only done stuff like this in countries where I knew the language.
So DH and I are trying to decide which we want to do - a tour group or going on our own. I want it to be a good experience for him, since it'll be his "Europe cherry." Any of you have any thoughts?
Re: Escorted Vacation or On your own?
Personally, I would pick to do it on my own (DH can come too, of course). But 1. I LOVE doing things like this. I love planning and I love vacationing. So planning a vacation is almost as fun as DOING the vacation. 2. I don't like tours. I hate being talked at. 3. I like going to places that are less tourist-y... i.e. I try to stay away from the tour group destinations. and 4. I REALLY love adventures. It takes a bit of adventure out of it for me going with a group.
I would consider doing a tour group if I thought it was going to be potentially dangerous or where DH and I don't speak the native language and there is a smaller probability of the locals speaking english... somewhere in the middle east, african safari, etc.
I've spent a decent amount of time in Europe and think that you can totally DIY your vacation if you wanted. People appreciate when you try to use their language but most folks speak English as well. I don't like being rushed around to things like you are on a tour so take it with a grain of salt. I enjoy sitting down to breakfast with a map and planning out my day. I really enjoy the Rick Steeves guides for traveling. They hit the big tourist spots of course but they also highlight some of the lesser known locales. Good stuff.
If I was going somewhere other than Europe where I wasn't confident in finding English speakers to help me and I couldn't reliably fake my way through a translation book (like China, I'd be hopelessly lost in China), I would be more inclined to do a tour.
OH! And I forgot to mention this other point...
If you, for instance, decide to visit a famous museum - they usually have guided tours from the Museum staff. Or, you can rent their headphones and take their audio tour at your own pace. So I guess I don't feel that you lose any of the experience by planning it on your own.
Happy planning! I'm so jealous.