The time-honored “Request permission to board” is asked for a very good reason. Remember that you are the casting director for creating your own utopia. Be careful whom you bring onboard with you. You will be “locked in a small room” with them for the duration of the cruise.
A study was done on the psychological conditions of many different living situations and it was found that blue water cruising had the most similarities psychologically to being in prison. There is no escape, and the qualities of your fellow inmates are of paramount importance.
Who you choose to crew with may be very different than who you choose to socialize with on shore. Unlike land life, each crewmember needs to understand that the safety of the crew and the boat must come before personal safety. Make a list of characteristics necessary in your crew. Here are some considerations for your list: Is this person willing to follow orders given by you, the skipper? If not, do not take this person, even if you are married to him or her. In an emergency situation, if your crewmembers do not trust you enough to follow orders, you may have a dangerous situation.
Unlike civilian land life, a boat situation requires one person to be in charge, and give assignments to the various crewmembers. If one crewmember doesn’t follow their orders, the breakdown in orchestration could turn an emergency into a disaster. Ask your friends if they are willing to follow orders first, and ask questions later, if you are in an emergency.
My rule on following orders is that everyone must follow orders first but they are free to ask why, as long as we are not in an emergency situation. And if anyone suggests a safer way of doing anything, we always defer to the safer method. This reassures and empowers new crewmembers quite a bit, knowing that if they feel the boat is heeling too much (for example), we will defer to their feeling of what is safe, and flatten the boat to their comfort.
Your list of what is desirable in a crewmember, or in the whole crew is going to be unique to you and your boat. You may want to make sure that, collectively, your crew has all the skills that you have as a captain. In case you are incapacitated, the steering, navigation, cooking, etc. can continue. It is a good idea for the crew to practice MOB procedures at some point early in the cruise.
Chartering with a group is about two things: people and money. Once you have chosen carefully who you want to share a charter boat with, the next issue is finances. The trip chair should get all the money upfront, and overcharge slightly.
You need all the money upfront to pay for the boat, and also to ascertain that everyone is actually committed to going. I organized a trip once where a woman kept telling me how excited she was to go. She had bought new sailing shoes, and a new hat, and some other technical gear. When I asked her for her portion of the charter fee she told me she couldn’t go because she didn’t have enough money! Getting the payment is the only way you know who is actually going.
For cancellations, the policy I have found works well is that if someone drops out, they can sell their share to someone else (that the group is comfortable with) or lose their deposit.
Overcharge slightly. You may run into unexpected expenses during the cruise; garbage fees, ice, gas for the dinghy, etc. If you overcharged, you have money in the kitty for unexpected necessities. It is much easier to refund everyone equally from the kitty than to try to collect a small amount from each person.
After a long cruise, buy back receipts from your crewmembers for things such as mooring fees, that may have had to be paid when the treasurer wasn’t available. After you have bought back all outstanding receipts, refund everyone equally from the remaining kitty.
When eating out, keep the cash in the family. This means that after everyone has put their cash on the table at a restaurant, the last to pay should throw down his credit card and scoop up all his crewmates’ cash. The next night a different crewmember takes the pot. This keeps the cash onboard the boat, in case it is needed for an emergency like major engine problems in a borough where credit cards are not accepted.
Hold a pre-cruise party. While the cruise is still in the planning phase, have a party to show photos of last year’s cruise to your intended location, and so that all potential crew members can meet each other and make sure they are compatible.
A pre-trip meeting should be held closer to the cruise date so that everyone can plan a menu together, talk about their food likes and dislikes and have the ubiquitous “coffee discussion.” This is where the types of coffee and coffee brewing paraphernalia to be brought along are debated in detail, along with the various methods of brewing onboard.
Even if you have a core group that you cruise with, it’s fun to add a few new sailors to each cruise to keep the excitement level high, and for the enjoyment of introducing new people to a hobby that is likely to take over their vacation time for the rest of their lives!