You had some must-see places, and you’ve sketched your days around them. 

Now you have to check against your constraints, then start to cut.


You can sketch these in, then fill them out as you get more information later. 

What constraints does the weather bring? For example, if a culture does siesta, there’s a reason. If you’ll be in Rome in August, you really should plan some afternoon downtime. Not an air-conditioned museum, either, because you’ll still be on your feet and tired. Take a real rest, at least in a comfy chair. You’ll find sleep comes easily. Plan around the hot hours. Be somewhere cool then.  

Seeing something special? Think about where the sun will be when you are there. If necessary, plan around that. For example, walking the Brooklyn Bridge is far better as a morning walk from Brooklyn with the sun behind you. Cooler, too.

What about other “lost” time? Will you need to do laundry, or line up at an information centre or a major attraction? Figure out your real arrival and departure timing. 

For arrival, work out how long it will take to get out of the train station or airport and to your hotel. Allow some time to hang up clothes and go “whew!”  THEN you can start doing stuff.  

Ensure that you can check in on arrival, because if not you’ll have to check your bags and find something to do. 

For departure day, make sure you’ve done all the thinking about when you need to leave. 

  • Allow for transportation, waiting for the transportation, check-in, security, and everything else. 
  • Add another half-hour and everything will be some much easier and less stressful. 
  • Remember that packing will probably take 10-15 minutes longer than you thought; I don’t know why, it just does. 
  • Plan for the pace of the slowest person in your group. 
  • Realize that the words “hurry up” do not work and just make everyone tense. It’s much easier to leave at a time you are SURE is too early. 
  • If you plan to do something on departure day before you get ready to go, watch the hotel’s checkout time. And build in a cushion to make sure you don’t have to rush to get back to the hotel in time. Allow for a traffic jam or subway delay or unfindable taxis.


We’ve found that the best strategy after that is NOT just taking your top few choices, unless they are must-see items. It’s better to identify key things and see what else fits with them. THIS is how you pack your days with cool things.  

It seems obvious that “what’s near the key places” is what you need, but that’s not quite right. ‘Near” must be measured in terms of how long it takes to get there (and if you’re walking, how much energy it takes from you)

  • In a city/town with a good transit system, you can draw a transit link between your hotel and your Key Place, and anything near that line is a possibility. Even places a few stops past your Key Place. 
  • What you really want to avoid is the situation where you need two buses, a train and a 20-minute walk to get from A to B. 
  • But watch it; it’s not enough to know that “place X is near a bus stop.” You have to know how often the bus runs. And whether there are any times when it doesn’t run, such as Sundays. 
  • This is why we often favour subways and frequent trains; you don’t have to factor in wait times.

One more trick: watch the walking

  • If you’ve just done a big museum, on foot, you need down time. Lunch might be it. But maybe your next stop shouldn’t be one you walk a long way to. 
  • Big evening? Maybe start the next day with a longish train ride, then work your way back. 

But don’t be hasty. Sometimes it’s good to leave things in and tag them “MAYBE.” 

  • If there’s something near a big museum, say, you might decide that you’ll see it if the museum doesn’t take all the time you allotted
  • Mark some fillers and substitutes. Have some smaller backups, places you may well not get to but are ready if you need them. Maybe something big will be cancelled, or you’ll decide not to have that big lunch, or maybe your outdoor day is rained out.  Have a couple for each day or each long travel leg. Have a couple near your hotel. 

But for now, you are ready to start planning your days.

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