Certs not required
I chartered in Tortola in March 2000 from the Moorings. It was my first charter. I broke nothing, thankfully. I have a Hunter 170 which I sailed for 2 years, previously a 14 foot O'Day Javalin. I also took a bareboat cruising course in New York City from Offshore Sailing School where I learned how to motor and sail a Hunter 41. The course was 3 only days. I then passed the US Sailing Basic Keelboat, Basic Cruising, and Bareboat Cruising certification tests. Tough tests which are crammed with questions about garbage (what's the deck of the cabin called? [sole]). The Moorings let me charter, based upon this limited experience. The sailing course I took was great since I was slightly less afraid to handle the larger boat -- we got a Beneteau 352 for my wife, daughter and me. I think, for first time charters, they want you to get a smaller boat. But, with The Moorings, you pay for insurance which covers everything except for a $500 deductible, so who cares if you trash the boat, which is unlikely. You may pay a bit more from The Moorings than at some places, but the boats are in great condition and no hassles. They did not require me to do any boat handling in front of them before I took the boat out. They will give you a skipper for the first day for free (we didn't, and didn't need one). The sailing course was great to learn how all of the mechanicals work on a cruising boat, plumbing, electrical, etc. AND the best thing about the course was learning how to handle an auxiliary powered boat, i.e. a big boat with an inboard motor. There ARE some real tricks to learn which make things much easier. As far as sailing the 35' boat, it was much easier than my 17' boat. And Tortola is the place to start out on your first charter. All the islands are within sight and <3 hours sailing away from one another. You do not HAVE to anchor anywhere. There are moorings you can pick up for $20 a night. We went for 7 nights. It was great. We're doing it again this March, in Tortola again with a Beneteau 413. Other big multi island companies in Tortola are probably OK too. Sunsail, Sunyacht. Stick to the bigger companies. The boats are in better condition. They all have internet web pages from which you can order catalogs. Moorings' website has a resume to fill out. They will respond within two weeks with a letter saying what boats they will let you charter.Good luck.