They say the most dangerous thing to have on a boat is a calendar. These devices will cause the crew to fret about the date, and act irrationally as they attempt to make landfall by a specific day.
What I find more dangerous than a calendar is a plan!
When you have plans, you probably have dates attached to these plans. That means that you will be in a rush to get somewhere in time. Worse yet, if the weather will not allow it, but you have a plan to stick to, you might ignore the more sensible option and instead power through the storm to keep to your plan.
When we set sail, be it in a bay or in the ocean, we have a loose construct of what we want to achieve. We set sail towards a specific place, but if the seas do not wish it, we do not argue. There have been many a time when we have made new plans when we are confronted by massive waves and powerful winds. We simply sail a course that feels safer and head to a destination that is in that path. This has led us to have much less stress as we explore the world by sail.
When we leave the Chesapeake Bay, we plan to go to Bermuda, but the winds are not going to allow that for at least another week. Instead, we will simply get out into the ocean and sail where the winds want us to go for a while. When we feel like we want to make landfall, we will head towards the nearest "easy entered by sail" port that we can see.
This approach has brought us to wonderful and fascinating places that we never knew existed until we anchored in their waters. We have met the nicest people in these small towns who have been a huge help to us as we make our journey. We plan to use this same approach when we leave the bay and enter the Atlantic Ocean.
Following the winds and currents, we will end up some place new that we have never been before, we will get to meet new people and restock with the local flavors of that new place. This will make getting to Bermuda very difficult, as we will make a million stops along the way, but for us, it is about the journey and not the destination.