One Place is Never Enough!: Making the Most of a Vacation

There are some important lessons I've learnt along the way. It's very easy to cram too much into your schedule and it's also very easy to keep adding extra places you want to visit. To avoid that, you do need to do a lot of planning right at the beginning. You need to be strict with yourself and realistic as well. How much time are you honestly going to need to see a city properly and how much money do you have? Can you really afford to add in somewhere else, with flight prices and gas prices not exactly cheap any longer?

Working out the budget is probably the easier side. All it takes is some calculation of how much it'll cost to get there, either driving or flying. It's worth shopping around and checking various airlines, which may go into airports near to where you're headed. For example, we're flying into Chicago's Midway Airport with Southwest in October, who came up with great fares. On the way out, we'll be heading for O'Hare Airport, as we picked up a great fare with JetBlue.

When it comes to deciding how long to allocate to each place, that's where you need to make some judgement calls. I always find that a good travel guidebook comes in handy to help you make those judgements. It allows you to browse what there is to see and do and work out a list of priorities for while you're there. Armed with that, you can start to work out how long it'll take to visit all of the places you want to see. If you're unsure, it's worth visiting the Globetrotting forum in the PassPorter message boards to ask for advice. The boards are full of well travelled people, who can help answer your questions.

One important thing to consider when travelling between destinations is how long that travelling is actually going to take. For drivers, there are some great websites, such as Mapquest which provide you with directions and details of how long it should take to get between A and B. If you're flying, you'll obviously know your scheduled departure and arrival time, but don't forget to factor in time at either end of your journey.

These days, you really need to aim to be at the airport a couple of hours before you're scheduled to take off to ensure that you've got time to check in, clear security and get to your gate. That perhaps explains why I tend to go for flights slightly later in the morning now. Somehow the thought of being at the airport ridiculously early just isn't that appealing.