I think your plan sounds good overall. Just a couple of observations.

I was going to mention the cruising permits also. I think "technically", you have to clear in at Road Bay *before* you go to the outer islands. I don't know how stringently they enforce that kind of thing but they seem to be a bit more formal on things than the rest of the area. Plus, the cruising fees are rather high (I think) so be prepared - like in the hundreds of dollars. Double-check.

Our itinerary is similar to yours with the difference that we start from Oyster Pond. We pre-clear out of St. Martin for the next day and then head up and around to Grande Case for the first night. Then we leave for Anguilla the next day. This means we don't have to go in to Anse Marcel to clear out. Don't know if you can pre-clear out from where you start or not.

I think it would be a long and potentially rough dinghy ride from Grande Case to Marcel.

We stay one night in Road Bay and then go around the North end and down to Orient Bay. You can anchor near Green Cay at the South end of the Bay or by Pinel. The best place to go ashore on Orient is at the South end at the Club Orient watersports hut. It's really the only place that is protected from the swells. Our first time, we just landed the dinghy in the surf by Pedros. Getting on shore wasn't bad but getting back out was, umm, a challenge.

I wrote it all up in a blog post Here if you want to read the gory details.

Note of course, that coming ashore at the South end of Orient means that you must walk through the Club Orient beach. Only you know whether that is "no big deal" or a deal breaker for your crew. The people there won't mind but you might feel odd if that is outside your comfort zone.

As noted elsewhere, don't expect to get dinner ashore at Orient. As far as I know, all the beach places close up by around 4:00 or 4:30. Same for the bars on Pinel. You *can* get dinner just off the beach in Orient Village (somewhat lengthy walk north from Club Orient but doable) but it will likely be dark when you are done and that makes getting back to the boat a bit dicey. If you do it, don't forget your flashlights and to leave your masthead light on.

There is no food (or anything for that matter) at Columbier on St. Barts - making it our favorite place...

We will be there this June so I'll have updated info after that if needed.

Happy to answer any other questions as well.

You'll have a blast.