Air-travel booking sites might all seem alike. Expedia or Travelocity — what's the difference? Sometimes nothing, such as when you're looking for the cheapest fare on a busy route and your dates are inflexible. But retirees (and writers like me) are often flexible, and that allows for better deals. I love Google's Flight Explorer feature, where you just select a region of the world and get shown all your options — mapped out in bar graphs — for the next two months and beyond. Other sites shine in specific situations. Routehappy.com, for one, picks flights with roomier seats or Wi-Fi, based on your preferences.
Video extra: How to save on airfare
The car-rental experience can be maddening, no matter how experienced the traveler. Once, when planning a weekend trip from New York City to Lake Placid, upstate, I thought I had scored a great deal on a compact car by renting in less expensive New Jersey. But I got stuck with an SUV, and my gas costs doubled, obliterating any savings. I like to use AutoSlash.com, which will monitor the changing market for better deals and rebook for you. And I advise everyone to do their homework when it comes to car rental insurance. Before you pick up the car, call your insurance agency and credit card provider and find out what they cover. Then call to confirm that the rental site has the size car you want.