Planning step 1: Everybody wins

First comes the excuse. Almost anything will do: a work trip with room in the suitcase for one more; the last concert of that band you love— well, it might be the last, you never know—or that moment when you realize certain family members are approaching the age they would rather pull out their molars than travel with parents ever, ever again. Whatever the excuse, the reason will be there. 

Now look at the map for the places you’ve always wanted to see.  

Everyone puts down their choices. It’s a shotgun approach at this stage, the only considerations being either a continental restriction or, if tacking onto a work trip, what can be reached in half a day by train from the point of justification.  Then the lists are compared and the places appearing on both lists go on to the 2^nd round. 

 At this point be sure to make concessions in regard to your list. Partly because someone else will have cities, sights you forgot all about and really do want to see. Strategically, however, these concessions, like any good sports trade, will provide leverage for the 3^rd round when the paring down begins. 

“Okay, Florence is not my first choice but let’s go with it and I’ll drop Rome for 2 museum picks and a B&B to be named later.”  

 This third stage involves the application of the time space continuum. Lacking a working Tardis means winnowing out places by means of serious logistical calculations and basic realism. So, how much time do you want to spend getting from here to there. At this point I am going to rule out car rental. Because it’s expensive and, depending on time, not always necessary.  That leaves trains and planes.

 Yes, train travel is fun and a way to cover ground but still see the countryside. While I would recommend the experience of an overnight train ride once in your life, the reality is that watching the world rush past your comfy train seat is not the same as exploring the world on foot.

There are cheap flights that will take you from one place to another in an hour instead of a day by train. 2 things to consider here. The fine print may reveal all sorts of charges that will inflate the ticket price. One airline is notorious for added charges to the point the owner is trying to find a way to have standing room on the plane. Yes, he would charge extra for the seat if he could and, probably, the air. 

They also, frequently, operate out of smaller airports which may mean you will end up spending most of the day getting to and from your time-saving flight.  Still, they are worth considering especially when you had no counter offer on the Athens trade. 

 The third stage is where the real horse trading sets in and you may want to cash in your trade considerations at this point. Be careful, make your trade too soon and you’ll lose it to a layover in Genoa.

Are we there yet? Here, sweet pea, take your blanket and have a nap because the fun has just begun. You know where you’re going and, in theory, how you’re getting there. Now it’s time for the real sweat work to begin.