Easy Caribbean for a new bareboater?

[Bavaria50]

A year ago (June 2023) I got my ASA104 bareboat cert for 50’ monohulls in the BVI’s on a week long course. A few weeks later (July2023) I took my family of 5 plus another sailing-experienced family of 3 to the exact same route that my course followed in the BVI, chartering a 43’ Darfour monohull. Following the same route with my family as we did in my course gave me the confidence to know how to sail it and what cool/fun things to do and see. We had an awesome time!

In a few weeks (August 2024) I’ll be getting my ASA114 sailing catamaran cert in San Francisco. I’d like to take my family of 5 back to the Caribbean, plus my sister, her SO and my 77 y/o active mom, for a week of cat sailing.

Caveat: my wife is starting school to get her paramedic cert (a one year program), so we can only go over winter break (unless we wait until next summer which is sooooo far away). The BVI is just too expensive over winter break, so I’m looking for a less expensive but still delightfully warm and interesting location to charter a cat end of December beginning of January.

My 2 questions are:
1. How do you sail a place you’ve never been and still enjoy it as much as if an experienced sailor had shown you the local scene (like my instructor did during my course). I’m concerned I would just follow charts and miss the intricacies of a location I know nothing about.

2. Any thoughts on less expensive locations during such a high season, where you can still jump in the water day or night and it’s lovely and safe to swim?

[Jebtrois]

Do your research and then participate in the adventure with everyone else rather than trying to constantly be the guide. Every place that is warm and tropical in the winter is experiencing it's high season. Florida might be less total cost if flights are cheaper, but otherwise you are competing with everyone else.