OK, due to a myriad of factors I ended up booking tickets into SJU arriving on a Friday around 4:00pm. We need to get to Tortola by the next morning for sure, but would like to get there that evening and do a sleep aboard. I just sent an email off to Island Birds for a quote so I'll see what they come back with. However, I suspect that they are going to be pretty expensive as with six in our party I think we are one above the limit for their smaller plane. If they come back too high I'll look into Air Margarita as recommended earlier in the thread since they look to be able to accommodate up to six passengers, though the luggage limit of 30 lbs per passenger may be an issue as I am the only guy on the trip and the others are my wife and four teenager girls. Any other suggestions of charter airlines I should look at? Is FlyBVI still a well regarded operator? Though I think we might run into the same pax issue with them as well. I'll also keep Silver/Cape Air in my back pocket in case the charter flights don't work. And I am certainly going to buy travel insurance for this one.

If anyone cares, the reasons we didn't fly into STT were that we had a travel credit with JetBlue that we have to use up this next year as well as some miles but apparently they don't fly into STT. Other airlines into STT were very either expensive for our dates, or the timing was problematic. I also tried to book Jet Blue all the way through to EIS but we would not have been able to use our credit or miles because of the SJU>EIS flight on Silver. At least that was the issue I was having on the website and I got sick of waiting on hold to talk to someone about it. In the end, after using our credit and miles to get to San Juan and if we book an air charter from there I think we'll be at about the same cost as we would have paid to get to EIS on one ticket. I was certainly warming up to the STT>ferry route so maybe next time.

Also, not that it matters, but we are not on Sea Tiger - I think someone else that contributed to this thread is though. From what I've heard Sea Tiger is a great boat with great owners and charter company (we've used TMM several times), but we are actually on a brand new Nautitech Open 44 with Horizon this trip. We toured that boat at the Miami Boat Show and really liked it and are considering buying one, so this is our opportunity to try before we potentially buy. We'll be on the water April 1-11 so if anyone crosses paths with us say hi!

Matt