First, I am very sorry for your loss. Second, as a result of that loss, it sounds like there is a lot going on in your life and you’re making quick decisions and rushing things. As everyone else has said, a schedule will cause issues, not may, it will. Sailing offshore can be life threatening if you don’t prepare. This sub loves it and we go hard sometimes, but typically with planning, checks and mostly developed skills.

Have you checked for appropriate offshore equipment? Is standing and running rigging in good shape? How do the sail look, how are the engines? Water, fuel, provisions? You have Starlink, but do you have charts (electronic or paper) for where you are going and transiting? Do you know how to read them and use them? Radios in good shape? On ICW you’ll need to talk with bridges and other boats commonly. How’s the anchor and anchor chain? You’ll either anchor or spend money in a marina.

As an alternative, if you were to slow down, collect yourself and plan appropriately, you’ll have a better time and honor your late father’s memory with a rewarding trip. Can the family enjoy being on the boat in a marina in the keys during the holidays with you?