How do you talk your wife (or friend) into a sailing vacation?

Recently I saw this question posted at and realized that this was probably a very common situation. In our case I lucked out… my wife, Claire, pushed me to take certification courses at Ocean Sailing Academy so we could charter. (Probably not the norm). Her interest in sailing is because she knows that I am passionate about it and it’s something we can enjoy together; though I’m sure she would really prefer to sit on a quiet beach for a week.

If you’re not so lucky, you may need to take a few “baby steps” to build interest before you go straight out and charter a bareboat. You might explain how private, flexible and peaceful a sailing charter can be, compared to a cruise ship with 1000’s of “strangers”, little flexibility and probably not too peaceful.

The really good news is that in most cases, you will discover that a crewed charter with a handful of friends will actually cost about the same or even less than a “luxury” cruise liner. (I know which I would vote for). Check out “Yachts vs. Cruise Ships: Day-to-Day Differences” for a basic comparison of a chartered sailboat vs. a cruise ship.

So what are some ideas for baby steps that could stir up some interest?

Idea #1: Share a crewed charter with a group of your friends or if you prefer, just book a crewed charter with your wife and even get training/certification at the same. The nice thing about a crewed charter (I am told) is that you can do as much or as little as you want. To find companies that offer these services, go to your favorite search engine (like Google) and type in all of the following words: crewed, sailing, and charter plus the location of interest, i.e. BVI. Be sure to use the word crewed and not crew.

Idea #2: My wife and I have not done this yet, but we are trying to get some of our Maine Windjammerfriends interested in charter sailing by going on one of the Windjammer cruises in Maine and letting someone else be responsible for all the details. Check out Maine Coast Windjammer Sailing Vacations – Maine Windjammer Association . The Maine Windjammer Association has boats from 46 to 132 feet and can accommodate from 6 to 40 guests. You can do as little or as much as you like on these cruises. There are also other windjammers in other parts of the world. Checkout Windjammer Barefoot Cruises .

Idea #3: Charter a boat on Lake Champlain in the summer with a crew for a week or a couple of days before you take the boat on your own. The nights are cool, the water refreshing, lots of places to explore, winds are good, lots of water, but always in sight of land (unless there is fog), no tides to worry about, and lots of safe and easy places to anchor. We have bareboat chartered on the lake the past three summers and although we find the selection of companies and boats limited, we have had great success with Navtours the last two summers. They have a number of boats just north of Plattsburgh, NY, on Mooney Bay.

Idea #4: Read the following great ideas on and you may get a few more ideas: Click Here!

Please share any other idea or thoughts you have by commenting below.

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