The boat is amost never the problem... Capt. Bligh is...
I was out there for two years with my wife. I lived on-board with her for another 1.5 years. And she is still with me and wants to go sailing again.
IMHO the biggest issue with women on-board is the loss of power / control. They are suddenly crew for this guy who takes on a new personality once the lines are cast off. You can ignore all the "Admiral" jokes, she is not in charge. My solutions included;
1. Have a staged plan. Do not plan directly for the Keys. Plan for Chesapeake for 3 months, then Marathon for 2 months, Bahamas for 2 months and then then Key West for 3 days (You can guess how much I like Key West). Let her pull the plug at any stage.
2. Give her veto right at the start of any trip. Explain that she has to give any leg of the journey an least two hours and if she still hates it you will turn back and wait for better conditions.
3. Teach her weather forecasting and let her handle the radio (VHF and SSB).
4. Help her get comfortable on night passages.
5. Have her do a Cruising course with a woman skipper. Take that skipper on your boat for a few days to help your wife get comfortable.
6. Try and not be a dick. (I failed on #6 on more than one occasion).
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