I thought I'd throw this out to anyone who might comment on a basic ROUNDTRIP sailplan aboard a 42' sailing Cat out of Marin, Martinique (southern Martinique). We are looking at a 16 night charter sail trip late June through early July. I'm an experienced (35+ yr) sailor with over 5k ocean miles including many multi-day offshore trips. 2 families of 3 each (6 total) aboard with 3 of the 4 adults having pretty solid sailing experience. I like having a "general" plan subject to all changes due to weather and general desires. Still, I like having a general plan.

So, here's the basic plan concept:

2 days/nights on southern end of Martinique after checking out boat.
Approx 4-5 days cruising down west coast of St Lucia.
Overnight sail out of southern end of St Lucia to Bequia (bypassing St Vincent to east)
Around 5 days cruising Grenadines (probably northern rather than southern islands/anchorages)
Transit up to St Vincent and spend 2 days
Overnite sail north (past St Lucia to east) onto Martinique
2 nights in Martinique before returning boat to charter base in Marin.

So someone might ask a few questions about the basic plan. Why skip over islands (St Vincent) just to then go to them on return (northern) trip back. Good question - we want to see the mountainous northern Windwards but do want to visit the low lying Grenadines - we think we'll have done this after St Lucia so skip over St V. with the option (plan) to return for a stopover on way back. We want to make certain we have enough time in the Grenadines in case weather changes our plans for return. And to be clear, we won't do the trip this way if weather is an issue and I'm used to weather planning.

As for the overnites - my wife and I love/understand them and the other family aboards wants the experience as well. We love experiencing overnites but even in good weather (the only way we'll do them) they can be a bit exhausting. They also allow us to jump around for longer trips (like this one) without sacrificing the days. Ultimately these will be a crew decision. We've got 2 overnites of approx 60-70 miles which is the distance we like that time of year (long days/short nights) spaced a week apart - we like that plan. Yes, its a charter and we've sailed charters (and many other sailboats) overnite - we have the experience, particular gear, and training to handle them. Don't worry about typical charter requirements - I have that one handled.

We've taken a quick look at C&I regs/ports of entry and it all looks reasonably doable without killing the trip with time spent in offices. (needs some more research tho)

We are looking for sportier, longer sails than typical in Leeward (Guadeloupe thru USVI) which we've done many times, and getting away from overly populated cruising grounds though a couple of nights in places like Rodney Bay, St Lucia and elsewhere isn't going to kill us - in fact, we like that in moderation - just not day after day.

We will need to figure out our safe "hole up" spots/options - I'll confirm those are always within reasonable shooting distance.

We also want to see/visit a high degree of varying landscapes - we think this trip/sailplan offers that.

Thanks for any thoughts - pro/con/other - that anyone might offer.

Best,

Kevin

Your itinerary sounds like a lot of fun and you have a good amount of time. Depending on your desire to spend time in the French islands, a few alternates to this could be:

Start in Grenada and do a one way up to Martinique. A while ago I saw that DYC was offering some very good pricing for one-ways in that direction with drop offs in St. Lucia and Martinique as this likely helps them get the boats back to their starting bases after the "normal" one way charter heading south. At that time of year the winds should be more easterly so the northbound legs should not be too bad.

Another option could be to start in Guadeloupe and work down to Grenada via Dominica, Martinique, etc. If I had the time, this would be my preference as you should be off the wind the whole way with some good sailing and interesting places.

Either way there are plenty of places to hole up if there is a tropical wave coming though.

We will be in that area for 10 days around the same time doing a round trip from St. Vincent. Have a good trip

So thanks for the feedback but our trip is set (R/T from Martinique). We'd have done a one way if we could have arranged that. For what its worth, we've been down the Leeward chain as far as Guadeloupe and love that - we feel that Guadeloupe is a hidden gem of a cruising ground (Americans unfamiliar with it...).