(Above, mural in downtown Milwaukee.)

With summer travel season approaching, you may be in the midst of planning that long anticipated vacation. I wanted to share an excerpt from my book. If you are anything like me when planning a trip, I attempt to “optimize” every decision in the planning process.

Over optimizing to me in the world of travel is having to get the best hotel deal, the best excursion, and always eating at restaurants with a 4.5 or better Yelp rating. Do you really need the best slice of pizza or the best deal on a hotel room where you stay for one night? When you find yourself spending time and even creating stress trying to perfect a decision, it is helpful to remind yourself of what you are optimizing for – cost, convenience, enjoyment, to slow down, to relax?

This excerpt specifically addresses planning an extended travel itinerary. This is written in the context of a 60 day trip, the subject of my book. I learned that I had to get away from this tendency to optimize very travel detail. It also provides some things to think about for summer travel planning.

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Fairly early in the trip, I realized that arranging and scheduling what I will call logistics could consume me if I did not set up some ground rules. When I say logistics, I mean nailing down the dates of traveling from one place to the next and booking the train segment, how many days at the next place, what hotel, how was I going to get around – public transport, could I walk when I got there, where to eat, deli, grocery store, pizza by the slice.

I have this drive to “optimize” each decision instead of landing with something that simply works and is good enough. For reference purposes, the Oxford dictionary defines optimize as to “make the best or most effective use of (a situation, opportunity, or resource).”  The emphasis on that definition are the words best and most. When you are at home, many of these logistics are taken care of or do not change much daily. We have our routines and habits and do not think much about them. That is not the case when we are traveling, and all these decisions are needed daily, and dates need to be coordinated. This is even more so when traveling alone.

To establish these ground rules for decision making, I reflected on lessons l learned in my extended travel experiment. In the end, I adopted the motto, “I will figure it out.” Whether it was understanding another mass transit system, finding a password to get into the Airbnb, or navigating another map, I will figure it out. For the purposes of this discussion, I defined extended travel as beyond two weeks and not part of a planned tour. The dynamics of travel change when you go beyond two weeks due to the constant “logistical” arrangements required, i.e., where to stay, transportation, where to eat, booking excursions in advance, what to do about laundry, etc.

1. Establish rules of thumb for travel.

When you travel for an extended period of time, especially if traveling solo, you are constantly making logistical decisions. It is exhausting. Where to stay, how to get there, what’s the four-digit code, and instructions for the Airbnb entrance, where to eat, what do I want to prioritize in terms of “sightseeing”, how many stars does the restaurant have, what if it rains the day of my booked walking tour?

This will wear you out over an extended period of time. Next thing you know, you are considering booking that direct flight home, ending your trip. With a travel partner, you can swap logistic duties back and forth. “You take the next three days; I’ll cover the three after that.” Solo travel does not allow for that. So, I established rules of thumb. Two nights or less, I use a hotel. Three or more, I consider Airbnb. But I am trending more towards hotels. Easier to check in, check out, and to find.

2. Rule of three.

I recently read “the Paradox of Choice” by Barry Schwartz. Fantastic book. It is very applicable to the multitude of decisions while traveling. The lesson I learned from the book was, despite what we want to believe, too many choices can sometimes be detrimental to our experience. Do we need 300 choices of cereal at the grocery store? When selecting a hotel, tour, or restaurant, I quickly (within three minutes) identify three options from a travel website.

I give myself five minutes to pick one of the three. Reminds me of an old golf saying about standing over a golf shot too long, “…think long, think wrong.” If I arrive at a city after dark, I use ride share instead of trying to decipher the transport system after twenty plus hours on a train. I occasionally use deli’s, pizza by the slice or ready-made sandwiches from a grocery store. Constantly eating out is exhausting and expensive. Basing your ultimate decision on three possibilities, leads to, at worst, a reasonable decision.

3. Identify a purpose for the trip holistically.

Without a specific purpose for an extended trip, being the “classic” tourist for a month plus can be exhausting. The purpose can be anything you want to choose. It can be visiting a single museum in each city. I say single museum because it can be overwhelming to visit multiple museums in every city visited. It can be taking a walking tour in each city. I have been on many of these, and they have all been worth the cost. The purpose can be to learn about the history of each place. It can be anything.

4. Theme for a particular city.

Pick a theme for each specific city, which will vary from city to city. For example, for me, Chicago was about art and architecture, Tucson was about mountains, Santa Barbara was simply being out in the sunshine. Looking forward at the itinerary, Boston, Philadelphia, and Washington, D.C. will be about history.

5. Consider the paid-for excursions.

Walking tours, hop-on, hop-off bus tours, or excursions out on the lake, bay, river, etc. These can be efficient ways to get a handle on the city and often, I find these to be excellent value. Typically, the tour guide is local and can add interesting commentary that is difficult to get otherwise and provide a perspective you would not otherwise experience. The historical walking tours in Boston, Philadelphia, and the Garden District of New Orleans later in my trip proved to be exceptional.

6. Book number 5 ahead of time.

The good ones sell out. I am partial to Trip Advisor. They store your booked excursions under your profile, which provides a quick reference as to what you have pending and then the details of the excursion, location, length, etc., and then keep the history of excursions completed.

7. Study the transportation system in advance of travel to the destination.

You do not need an exhaustive study of it. Just a quick overview. Although it is hard to find paper maps these days, I find them much better to get a handle on the geography of a city with a paper map. These are available at most tourist information sites, typically in the center of town.

The following two items are the best sources of information while traveling:

8. Tourist information centers.

These can be a plethora of useful information. They are typically good for making excursion recommendations, and they can mail postcards. I am a big fan of tourist information centers.

9. Ask other travelers.

Do not be shy. They love to help. Who does not like to talk about the places that have traveled? Having said that, do not drop something on your list after you have heard one negative review.

10. Sometimes, just go with what you know.

I want to find that unique “local” place, but sometimes it is good to go with the known, i.e., Starbucks. I have lugged my backpack a mile out of the way for that unique coffee shop experience, only to wish afterwards that I had gone with a more convenient choice. Note that this is a “sometimes” sort of thing. When I travel, I want to experience local places I could not get back home. It just does not have to be the goal on every decision.

One final thought on this and the most important. You do not always need to perfect every decision on the trip. Sitting on the park bench and reading a book, spending a lazy afternoon at the hotel pool is ok. As with life in general, the pressure to feel the need to perfect every aspect will not give the best results, and it will exhaust you. Over optimizing to me in the world of travel is having to get the best hotel deal, the best excursion, and always eating at restaurants with five-star ratings.

Do you really need the best slice of pizza or the best deal on a hotel room where you stay for one night? When you find yourself spending time and even creating stress trying to perfect a decision, it is helpful to remind yourself of what you are optimizing for – cost, convenience, enjoyment, to slow down, to relax?

Hope this helps with your summer travel planning.

Link to book on travel.