How to Book Flights & Hotel Rooms in Several Different Cities

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Plant yourself in front of the computer

It begins with the Internet - at least in this day and age (sorry travel agents). Sites such as Expedia, Orbitz and Travelocity offer simple options for booking flights to multiple cities. They also offer many options for hotel accommodations, as well as discounts on all of the above. You may want to just book your travel on these sites or just your hotel(s) -- it's up to you.

Plan your flights. If you are flying to Europe, it is usually cheapest to fly to a city such as London and then take a cheap flight on Ryan Air or similar type low-cost air carrier for inter-continent flights. For example, a flight from London to Prague and back costs the US equivalent of $120 even in the late summer. Ryan Air is also currently offering a few free flights on certain legs -- as of this writing. Check the site for details. You can also book your main carrier such as British Airways to fly all the legs in many cases, but you are likely to pay more.

Book Your Hotels. Google search under "Bed and Breakfasts" or "cheap hotels" and you might find some better options than what an Orbitz has to offer (but not necessarily). It depends on what you are after. Hotels, also, are more negotiable with their rates than are airlines. You can haggle with hotel desk clerks if you know what you are doing -- it's always worth a try. This is obviously a much more ambitious plan in high season when the hoteliers aren't fighting for business. And in popular cities, many times they don't have to worry about booking up. But if you are flying to the outskirts of Ireland in the dead of winter, you probably have a good chance of finding something very affordable.

Call the hotels regarding their policies. If you don't have $250 to spare on each of your credit cards, you could be in for a nightmarish surprise when Hotel A places a hold on your charge card; then when you leave for destination B two days later, Hotel B also places a hold on your card, and so forth. It can add up. A simple call in advance to clarify exactly what they need in terms of a deposit is a good way to flesh out your budget. Whatever you do, plan on buying your little luxuries off site -- those hotel mini bars are a very bad idea, except for the wealthy!

Double check your flight information before you head to the airport. These are dicey times for the airlines. For anyone who was trapped when American had to cancel its flights this spring, it was a reminder that nothing can be taken for granted when it comes to air travel. Have a contingency plan. Airlines will, of course, try to accommodate you - but that doesn't mean you have a day to spare sitting in an airport lobby waiting to get rebooked! If you can possibly take a bus or train in the event of a flight cancellation, it's not a bad option -- This is obviously not possible if you are crossing the Pacific for that first Hawaiian vacay, though. So hang loose. The airlines do want to accommodate you. American was very good about refunding its passengers' money or rescheduling flights, as will other airlines should it ever happen to you.