Plnnr is a neat web app that saves you the trouble of hiring a tour guide for your next holiday by providing you with smart itineraries that are customised based on criteria you provide. It'll even recommend a convenient hotel in your price range.
You start by signing up and providing a little information about your interests. Plnnr doesn't support every city you might want to visit, but it offers a number of popular destinations. Once you select where you headed, you let it know what kind of places you want to see, how many days you have to see them, what kind of hotel you're looking for, and a few other details. Next, it puts all that information together and comes up with an itinerary and you can check it out. Before you commit, you can tell it how you feel about each choice. If there's something you don't like, veto it. If it's at a bad time in the itinerary, say so. If you just don't know what it is, click on its name and you'll get an explanation along with photos. Once you're done, print it out and take it with you on holidays.
Plnnr is completely free to use, so go give it a try if you're looking for things to do next time you travel.