My wife and I are trying to book our first bareboat charter in the BVI next year. We are both ASA Basic Keelboat (101), Coatal Cruising (103), and Bareboat (104) certified. I went on to earn my ASA Navigation (105) certification as well. We have done 4 crewed charters, 3 in the BVI and 1 in the Florida keys.
I also added on my sailing resume that I am currently enrolled in a school pursuing my 50 ton Master's, and have owned power boats for 10+ years.
I fully understand that I am no old salt, but I thought I had sufficient experience to charter. I am attempting to charter a 40 foot monohull and the bareboat company has told me that after my resume review I will be required to hire a captain for the first 2 days. Is this common?
Having not read your resume I would say it's not necessarily uncommon to have a skipper required. I work for a charter company and do not approve resumes, I do see a fair number of them. Some charter companies are more wary than others when it comes to protecting the assets that the owners have been so gracious to entrust them with. I go out with guests for three reasons:
1) The charter guest requested a skipper. The time frame for the skipper is determined well ahead of time anywhere from one day to the entire period of the charter.
2) The owner of the company required the charterer to take a skipper typically because of resume concerns. Again this is determined well ahead of time. This is usually one or two days depending on how well the guest is handling the boat and systems. I've been scheduled to go out for 2-3 days before and gotten off early because the guests are doing so well there is not a real need to keep me on the boat longer.
3) I've done a briefing on a boat and it's clear that either the charter guest has greatly embellished their resume, they haven't sailed in a very long time and skills they might have had once have greatly diminished, or for whatever reason the charterer just can't demonstrate VERY basic skills during the sailcheck. This is the most awkward and my least favorite part of the job and thankfully only happens a couple of times a year probably because the company is so stringent on resumes. There is no way to know if a skipper for a day or two or more is needed. It is all dependent on the charter. I sure don't want to mess up somebody's vacation plans! In the same sense if somebody can't figure out how to get the sails up (or out) and get through a tack or two, why would it be responsible to turn them loose on something worth a few hundred thousand dollars when there is a very good chance they could hurt themselves, some one else or the boat?
I don't know what the magic formula is to "pass" with TMM or anybody else. Reading your post, the things that would concern me are that you don't describe any bareboat experience at all. You don't describe owning a similar sized sailboat to 40'. From a charter company perspective I would assume that crewed charters are looked at the same as if you said you had been on a cruise ship. The other thing is that for a first bareboat charter for a couple, you don't mention having other crew along, starting on a 40' could be seen as a negative. Charter companies are in the business of sending people out on boats. Boats on docks do NOT make money.
My suggestions are, if you know you have all the necessary skills to bareboat a 40' boat, accept the skipper for 2 days and learn from him. You will be out what, $300-$400? What percentage of your total trip expense is that? You've taken the time and spent the money to get ASA certifications, why not continue your education with another experienced sailor? Any skipper that is worth a darn will recognize your abilities and leave you alone as soon as is practical. TMM is a reputable outfit, and technically our competition, and I would be utterly amazed to learn they were not using good skippers that would try and stretch a trip out for no reason. Or, see if a smaller boat is available that avoids the skipper requirement. Or, wrangle up some friends with sailing experience to go along with you. Or, ignore cost and go someplace that looks at your credit card limit as the measure of the skills needed to go. Some of the largest companies come to mind.
Whatever you decide to do, have fun, relax and be safe.