I used to tutor, and I have a terrible sense of direction, too.

It's important to notice distant landmarks, first of all. For example, in my city I know that the mountains are to the north.

Start learning the major streets, what's on the streets, and how they cross each other. You can try learning one street at a time. As in, "That's the street the Target is on. Oh, and there's the McDonald's too. If I keep going south, the street changes names." etc.

Load up a route on your phone, study the route, put the phone in your back pocket (or wherever), follow the route from memory, pay attention to the surroundings around you, then take the same route back.

Now of course, first choose a route that is easy with few turns.

After a while, next time look at the map without a routing, and decide what route to take.

Think about the sun. Where is it in the morning? Where is it at noon, in the afternoon, etc?

Use the sun to help orient yourself. Maybe you take some unfamiliar trails that go east or south or whatever from where you are. So, you know that if you go west or north it wherever from where you ended up, you'll be closer to where you started and more likely to recognize your surroundings.

I suppose this requires a mental map of sorts but that's easy to Google before you get on your bike.

Sometimes you literally just need to know what direction to head, and you'll figure it out from there.

Look at a map of your city closely. Understand the major streets and the directions they go. Explore the city and don't be afraid to get lost, you have your google maps to turn to if you do.

I find that by forcing myself to go out without a map and find my own way back home, I’ll quickly learn how to get there. Also, mentally I kinda keep track of the fewest turns to my destination. The key is not to be afraid to get lost, failure is an excellent motivator. Get lost, get lost again. You’ll get it.

Repetition is huge!

I also like to put google maps up on my phone connected to headphones, so while I bike the directions cut in over my music. Helps me learn more clearly than stopping to chekc the mao

Spend time looking at a map. Familiarize yourself with landmarks - bodies of water, mountains, large buildings, major roads. Figure out the approximate direction of major roads., Orientation of buildings or parks. Pay attention to which way is north.

Comment about the sun is really good too.

Go without a map, and follow your sense of direction. Only pull up the map if you get lost. This will teach you to think more on your own, instead of following what the map says.

Learn landmarks.

They can differ per person.

My wife remembers shops, I remember building and crossing shapes and layouts.

Besides what others have said imagine the map in your head and follow your path in your head as you travel.

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Thanks everyone for taking the time to help me out. I appreciate all of your tips! I look forward to taking my bike out when the weather gets warmer, and trying all of your advice out. I’ve definitely been treating Google maps on my phone like a life raft, and it seems I just gotta do like a Jack and let go of the door. Force myself to recognize landmarks, sun location, etc.

Practice copying down a map of your city onto a piece of paper