As one gains experience, the notion of what a long trip is changes. When I started sailing 40 years a 12 mile trip to the next bay was a big adventure. The first trip across Lake Ontario (~50 miles) was undertaken with charts, a compass and a boom box. State of the art equipment for 1984. The last long trip I took was 400 miles, quite a difference from 12.I remember my first 'long distance' sail. After 1 year of sailing experience I had bought a new to me boat and I needed to deliver the boat from the brokerage to my home port. The distance was 35nm and started in a new port. I was super nervous about the trip
A little apprehension about a longer trip is still experienced and systems and weather are checked multiple times before we cast off. Its a good thing, being complacent is an invitation to trouble.