Hello TTO community!

We are a family of 5 (mom, dad, and kids aged 13, 11, and 9, all with sailing experience) who are super excited about our first visit to the BVI and our first ever bareboat charter. And to be perfectly honest, my wife and I are a bit nervous about it as well, but everyone said BVI is the perfect place for your first bareboat cruise, so here we go! We have been reading the cruising guide and lurking on this forum and the FB group for a while, but real prep time is upon is. Here’s some info that may be relevant before I ask a couple of questions.

Boat: 41’ Monohull chartered from Horizon YC June 16-26. We originally were looking for a 7 day charter and asked Horizon to price match an offer from another company, and they offered us their 10 days for price of 7 deal (which wasn’t in effect at the time, this was January). I only say this because we feel like these are bonus days and plan to stay on the boat when we otherwise might have stayed in a hotel before/after cruise.

Getting there/back: Our flight from Miami arrives at STT on Thursday June 16 at 11:21 AM and we have tix for the Roadtown Fast Ferry departing at 2:30 pm. Our flight departs STT Sunday June 26 at 5:35 PM and we have tix on Native Son departing Roadtown at 11:30 am earlier that day.

Our experience: I have been sailing ~25 years and my wife for about 8. We own a Corsair F-27 trimaran and are fortunate to be able to sail year-round in Biscayne Bay and the Keys, and are used to docking our 18’ beam at crowded crazy Miami marinas. But our F27 has an outboard. I have never skippered a monohull over 30’ in length and have no experience at all maneuvering with an inboard engine.

As a result, HYC was not-surprisingly concerned after reviews of our sailing resumes. In response, I offered that we would be fine with spending the first day with a skipper who could give us docking lessons as well as going over everything else with the boat. The end result is that on Friday June 27 “ You will be required to have a check-out skipper who will accompany you for the first 24-hrs OR to the first anchorage of your charter. Upon approval of that skipper you will be allowed to continue your bareboat charter. If you are not approved, you will be required to hire a skipper for the duration of your charter”. I am fine of spending the first full day (2nd day of charter) with a check-out skipper (we suggested it) but it will put a serious damper on our plans to have to hire a skipper for the rest of the cruise! (Yes I know it's in the contract I signed).

Questions (I’m sure I’ll have more later):

Do I need to be seriously worried about the check-out cruise? Do you have to be extremely incompetent/overconfident to fail these, or is it actually common? Should I expect some level of friendly instruction or are they going to be looking over my shoulder and judging my every move from the git-go?

Our boat has 3 double berths for our five. Should I propose to HYC that we do a long day sail on June 17, including picking up a mooring ball somewhere, and then return to Nanny Cay that evening to drop off the skipper, and sail out on our own on the morning of June 18? I don’t see how having the check-out skipper sleep on our boat proves anything additional. Or should we go with what they suggest (or should we expect them not to budge?).

I understand there is a grocery store next to the HYC offices. We plan to (mostly) provision ourselves. Will we have time to do this after arriving June 16 (I expect we will not arrive in Nanny Cay until what … perhaps 5 pm)? Or should we plan to provision the morning of June 17 before the check-out sail begins? When should we try to schedule our chart briefing?

Do all of our ferries and flight times look okay as far as not missing flights or ferries? On the last day (Sunday 26), to do the boat return/check-in and catch the 11:30 am ferry out, do we need to plan to spend the last night (Saturday June 25) on the boat in the marina, or is there still enough time to spend that night are someplace close like Cooper’s or Norman’s and still return in time without a lot of stress?

Given these constraints, do you have itinerary suggestions? I originally had my heart set on going to Anegada, but given the potential loss of a day or two to the check-out, that’s probably not going to happen. Which is ok – HYC may not let us anyway, and Anegada sounds more like the Keys (flat) that we are used to, so we can save it for next time. But would you give up Jost Van Dyke for Anegada if it was one or the other?

Our boat has A/C. Don’t know how much we’ll need it, but it was one thing my wife put her foot down on. Should we expect to have to get fuel somewhere along the way because of generator use? Or will one tank be plenty? We did not get the pre-paid fuel option. Should we?

Do we need to pay extra for a wifi/internet package in order to have a chance on Boaty Ball, or will a 5G iPhone (on T-Mobile, ughh) be sufficient?

We are avid snorkelers and plan to bring our own masks but use HYC fins. Good idea? We like to paddle board. Rent one from HYC worth it? What about other water toys to keep the kids happy? Kind of a rip-off to rent from the charter company, or go for it?

OK that’s a short novel’s worth so I’ll stop for now. Thanks for reading!