We have done this a few different ways and happy to share what we have done - which has some pros and cons. We have kids so an easy entrance was important to us. We have had our captain - who is amazing, check our boat out of Tortola (check out of BVI) - we had the provisions, fishing gear, sporting rental all delivered to our boat. He checked the boat out of BVI and moored at Caneel Bay or Leinster Bay at St Johns. We landed, headed to redhook - from there we have done 3 things. One, he picked us up at redhook, 2nd - we had a water taxi take us directly to the boat being moored at Caneel Bay, 3rd - we took the ferry to St. John's, loaded up the taxi and took it to Leinster Bay to a boat that was moored, provisions in the fridge, and a glass of wine waiting for us. We spent a couple of days on St. Johns and then checked back in to the BVI for the rest of our trip. We love St John's so that was part of the plan. I would recommend the 2nd or the 3rd option due to the issues with mooring balls. The first works well depending on the day and season.