Dream to sail the U.S.A coast?

First learning how to sail would be the thing to do. After that provisioning is simple , figure out how many days you need food for make a menu for that many days ie: 6 days = 6 breakfasts 6 lunchs 6 dinners plus snacks. Depends on how much you like to eat, also how big a boat you have. If your travelling coastal you can always stop for supplies. If you coming down the east coast you can do the icw protected water all the way, it's a breeze. West coast is a different story. Weather is always the deciding factor for either side. It's much nicer in warm weather. Buy a couple of sailing Magazines and do some reading. Latts and Atts or Cruising world both available at west marine or online.

Staying in Harbors is easy there are guide books for both side of the country. Charlies charts for the west coast, several other publications for the ICW.

Good Luck Rob Currently sailing in Ecuador, but have sailed both coasts

Read some of the costal cruising guides for the coast you want to sail.

Volunteer to crew on other peoples boats to help them with the passage. You gain a lot from working under a good skipper.

Read the book Tinkerbell about a guy from Mass who sailed across Atlantic in 14 foot sail boat called Tinkerbell. Very interesting covers alot you may never think of.Such as wind and sea currents shipping lanes falling overboard,capsizing,extra flotation,sleeping,how to package food etc.....take pics and notes to write a book when your done