We got started in boating 9-10 years ago, wondering about the very same questions. Started by spending a lot of time reading through this forum and just absorbing info. Step 2 was to get our boating certificates (completely online at that time) which we used as another important learning opportunity.
After that we rented on Winnisquam for a couple of weekdays. That gave us a sense of whether we were interested in spending the bulk of a day on the water. It also provided a low-stress environment as Winnisquam is relatively easy to navigate, and easy to stay out of trouble. From that experience we learned that we were in fact interested in getting into boating full time, that we could actually handle the very basics of boating and navigation. Also learned a few other things, like a bimini top was going to be a must-have.
After that we got into the hard part - where do we want to be? For us, Winnisquam was a great lake to be on if you had a house. Great for skiing/tubing etc. but not sufficiently interesting to be there just as boaters. So Winnipesaukee it was, approached with a willingness to learn and constant respect (which we maintain even today). We purchased our boat from a reputable Winnipesaukee marina and rented a slip there. It was over a Labor Day weekend so we had a month or so before season end to start exploring and getting some experience without the July-August crowds.
We have availed ourselves of training and advice from the sales and service staff from the start, and continue to learn about the lake and handling our boat.
Winnipesaukee can be a challenge, particularly on July-August weekends, and particularly in the Weirs area. Getting a start on Winnisquam or similar lake can help build confidence in a lower-stress environment.
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NHskier
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