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.

[JeffDPT]

Shop around for prices. Include airfare into your budgeting, The Keys have a few companies so Jebtrois has a good idea. This forum and the charter company websites give good insight into itineraries. TripAdvisor forums have good info on specific locations inc. restaurants, beaches, obviously sightseeing.
Have fun,

[dougweibel]

The BVI is by far the easiest cruising ground in the north and eastern Caribbean in my opinion. Sailing distances are very short and moorings are plentiful and easy to arrange. In the eastern Caribbean take a close look at how many anchorages each island has as you won't want to be doing a lot of island hopping on a relatively short charter. A 40 mile passage and checking in to a new country will pretty well kill a full day, and another day for the return trip.

I don't think you will find anywhere in the Caribbean inexpensive late December / early January. There are too many other people with your calendar restrictions interested in going around the same time. Possibly Martinique, just due to the massive size of the charter fleets there. Or, the Abacos (Bahamas) though that may or may not fit your definition of warm in December and January.

As far as your question about sailing places you have never been I think comfort just comes with experience. It doesn't take much time to give yourself a chart briefing and familiarize yourself with the issues you will have sailing any given day and route. Current is probably the thing that might most confound an inexperienced captain so find out if that will be an issue for your destination. Guide books are quite helpful and available for pretty much any cruising area you could charter. Check out activecaptain.com and navily.com as resources to pick out, and find issues with, anchorages.

[Kinkircating]

Personally, I’d highly recommend sailing on the shoulder seasons and not in high season. Smack dab in the middle of hurricane season you’ll get the place to yourself practically (which we prefer). The weather is just as nice, but all the best spots aren’t so damn crowded and makes it much more comfortable to learn and build your skills.

BVI is essentially like a giant bathtub that it’s hard to get into too much trouble, but you will be picking up moorings everywhere instead of anchoring. I really like the Bahamas because it adds a bit to the learning experience with lots of anchoring and checking your charts/weather/tides etc.

I’d also recommend the one way run from St Vincent to Grenada, not for your first charter, but it gives you that opportunity to feel some real breeze and ocean swell between the islands.

Honestly, don’t overthink it just get out there and start doing it. Buy whatever the “extra insurance” is that they offer so you aren’t constantly worrying about it, and have a great time. I started the same process 10 years ago and I look back now on my first 3-4 charters and just shake my head partially in laughter at how little I knew, and partially out of “what in the hell were they thinking throwing me the keys to this $500k catamaran” lol. It’s just something you have to go through to see if the juice is worth the squeeze for you, good luck!