Yes, we would be hiring him through Sunsail.

Since we live in California, there is no easy way to fly to Tortola. It is either a red eye or overnight in St Thomas or San Juan. Ferries or expensive and almost sold out Sea Bourne schedule.

We were thinking if we flew to St Thomas on a red eye our Sunsail captain could check out the boat and sail over to Red Hook (? which is the closest dock?) and pick us up. We can arrive in STT at 1:23pm and all will have carry on luggage.