Itinerary Planning 101

Itinerary Planning 101

We have put together a LOT of itineraries based on our trips and research because we’ve been asked a lot and also plan a lot. But you too can plan a trip and get the cost savings and flexibility you may not get from an organized tour. Here are the basics of planning:

  1. Decide what you want to see. This may seem straightforward but a lot of guidebooks and websites make it sound like everything is the same / great. Spend some time reading. Opinionated guides (like us – or Rick Steves) may help. Lonely Planet is great and comprehensive but pretty much the opposite of opinionated / they make everything sound great (it’s not). Pay attention to UNESCO world heritage sites as they’re usually unique; pay attention to popular sites (they’re popular for a reason and usually worth it), avoid gimmicky sites. You may need to check more than one guidebook. Search out things that really are unique (consider consulting sources like Atlas Obscura). Lately we’ve also been reading Conde Naste and Culture Trip for ideas. You should also look at itineraries from major tour companies (National Geographic for example) as they tend to hit the highlights. Try and mix up cities and rural areas / villages / natural sites for variety. Online blogs and information may be the new way to look but often also lack opinions so do your homework either way.
  2. Link your sites together. Several rules of thumb we’ve developed through the years:
    • Maximum about 4 hours driving between stays. Look at google maps for drive time in advance. You can do longer on trains (especially overnight like nightjet) but think about the amount of travel vs. sight-seeing time. Use Google Maps or Apple Maps for drive time and Rome2Rio to get a quick estimate of other transit times.
    • In general a couple days stay per location is way less stressful than a day at each site. Try and make many or most stays a couple days or more.
    • If you are going to small towns / villages it is easy to link them by car but can be challenging by public transit as the busses / trains just don’t go that often. Plan accordingly.
    • Trains are almost always best for linking cities. Planes may be faster in theory and even cheaper but by the time you figure travel to the airport and security the train almost always wins (at least in Europe). Cars are fine if you have one to see smaller places but require worrying about parking and driving in cities can be a nightmare. And if you have an option for a boat or ferry its almost always the most pleasant way to travel (though not the fastest).
  3. Don’t over do it. This is a tough lesson to learn. Travel is intensified living and we have a tendency to want to cram everything in. Yet time enjoying the outdoor cafe may be as important as seeing another site. Don’t pass up sites but be reasonable. One major museum is enough museum for one day. If you plan too much you may fail / be stressed. We have been told that our trips see a lot more than many people think possible – but be careful not to over do it is the bottom line.
  4. Plan your lodging in advance. Once upon a time we’d just roll into town and look for a place to stay. That was long ago, This adds time and stress and you’ll end up with an inferior lodging at a higher price. In the days of Internet it’s better to book ahead. See our page on choosing lodging.
  5. Likewise plan your popular sites / excursions / museums in advance. In museums and popular attractions advance tickets guarantee admission and may let you skip the lines. Somewhat less flexibility but a very reasonable trade off.
  6. Plan around walking tours. Sometimes a tour leaves at a set time. If you want that tour be sure and get there in time. In general we think walking tours are a great way to find out the history / stories of a place and are worth seeking out. Check guidebooks for recommendations, Get Your Guide or Tours By Locals are other sites to looks at.
  7. Expect problems and be flexible. If a flight get cancelled – don’t get upset – be flexible and make other plans. Things will go wrong but you can change plans.
  8. Book refundable rooms. It will cost a bit more but after the pandemic / some health things that came up it’s really worth it to book refundable whenever possible (see #7)
  9. Meal planning.
    • You will notice that we suggest places to eat / get drinks, etc. We have found that it doesn’t necessarily cost that much more to have a truly phenomenal / memorable meal as one that is is just OK. We choose based on a variety of recommendations including Michelin guide, Conde Naste, Time Out, etc. If you check several and the place is listed in several it’s probably a good bet. This is one area to be wary of guidebooks – they may have OK recommendations but we usually check and verify with other sources as we’ve had some mediocre to bad experiences with just guidebook suggestions.
    • Lunch can be a big time drain when you’re on the move. At least once in a while it makes sense to grab bread / cheese / cold cuts / fruit at the local market or grocery and do a quick picnic. It is also easy to overdo the picnic thing so be judicious. By the way foreign groceries are almost always worth a visit as a cultural experience.
    • If breakfast is included with your room, great. Take advantage. If not check the price. Most of the time it will be cheaper, faster, and better to get your coffee and breakfast at a nearby cafe than at your lodging.
  10. Sites. Never ever skip an attraction just due to the cost. If it’s a marginal thing or super expensive, sure. But the reason you are here is to see the sites. Skimp on lodgings/ food but cough up the money for the important attractions.
  11. Local highlights. You’ll want to engage in the local fun. It’s not all about cute villages and architecture. If a place is famous for sheep dogs find a sheep dog demonstration. If calvados is a thing in your area be sure and arrange a tasting / visit. If the town is famous for hot springs pack a swimsuit and towel and jump in. Take the time / effort to seek these out and plan.
  12. Timing. These days a lot of sites become overrun (usually mid day) with tour buses / cruise ship passengers. If you can arrive early (or sometimes late) you can have a much more enjoyable experience.

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