First step is to figure out if you are a planner or prefer to wing it or maybe a combination of both. The next is deciding how much time you have to travel as that might impact your approach. Also, how important is your physical environment to your well being? If you plan, prepared to have your plans disrupted. If you don’t plan, prepared to alter course and for the occasional annoyance and scrambling. Either way, prepare for some disappointment and some surprise. I find that I do best without a plan as I prefer to show up somewhere and see if it speaks to me. It became clear to me in my travels that my physical environment matters – not that I need the fanciest or nicest place, in fact I prefer a slight bit of shabby chic, but I do need some nature around or architectural diversity. More often than not when I made a reservation somewhere, it turned out I was sometimes locked into somewhere I did not want to be or want to stay. At times this was a good thing as it forced me to explore areas I would have left, but in other cases, I just ended up feeling a bit down on myself for being stuck and not having the freedom to move along. And yes, I know I could have just moved on and viewed the lodging price as a sunk cost but I was being cheap in my travels so my threshold was about $40 for when I gave myself permission to walk away. In all my travels, including multiple countries, I have yet to run into a situation where I could not find somewhere to stay. This occasionally meant asking around (bartenders, front desk hotel staff, internet search, and in at least one instance, folks out in their yards) for anyone who knew of a vacant rented room.
My biggest challenge was what to see not only at each destination, but also along the way. There are so many sites with guides on what to do, where to eat, where to stay, you name it. You may want to figure out which sites align with your interests. For instance, I find that tripadvisor caters to families and most of the top ten things to do are not things I find interesting. Google can be a good source though much is catered to a younger crowd. I do use yelp quite a bit, especially for food and coffee (I do read the reviews to see the reason for the ratings) and have even found it helpful occasionally for finding dispersed camping and activities. Eater.com is a great food site though won’t cover most small towns. All Trails is great if you want to walk or hike. One site that is kind of neat is wanderlog.com which will give you things to see along the way and I found some pretty interesting side trips this way. There are some regional sites and travel bloggers that can be great as they have inside knowledge rather than just ratings from a bunch of tourists.
One other source for all kinds of things is ChatGPT. For instance, you can give it patterns to follow (there are too many to go into) and have it spit back information. Sometimes it takes rewording and refining but once you can give the right prompt (what you type in), the information can be invaluable. For instance, here is something I typed in today. I gave it the following prompts: First I typed in “When I say “destination-destination” I mean the point to point destination. Sometimes I will have more than two destinations. When I give you destinations I would like you to give me specific unique things to see involving nature between them.” To which ChatGPT responded, “Understood! When you provide me with specific point-to-point destinations or multiple destinations, I’ll give you specific unique natural attractions and points of interest to see between those locations. Please go ahead and let me know the destinations you have in mind, and I’ll provide you with nature-related recommendations for your journey.” I then typed and received the following which does not give pictures but does give me some direction on things to look into. I refined my criteria further to tell it what highway I would take (I know that Pinnacles is off Highway 101) to limit how many miles out of the way I wanted to go and received what you see in the second screenshot.
Another note on maps. I tend to prefer Apple Maps for my GPS as I found that Google was not up to date on road closures during a storm. If you use Apple Maps (and maybe Google, but not sure), when you type in multiple destinations, it will not show you the best route but rather take you on the freeway which can add hours. For instance, recently I was driving to St. George, Utah from Mammoth Lakes, California and wanted to stop for a coffee in Bishop. I chose the route that went over the mountain and was the shortest point to point. However, I then added a stop at a coffee shop in Bishop and noticed much too late that the map had rerouted me through Las Vegas, wasting many hours and adding a lot of miles to my route. So, if you are putting in stops that are far apart, I suggest you enter at each stop as you go.