Not sure if I am allowed to post here or not. If I am not - moderator, just delete it. No worries.
We (and I mean we) borrowed a 22 foot Tanzer sailboat for a summer (1995). We have a four month season where we live. At that point we had a son in high school and a daughter in college.
I was going to a conference in Toronto the following April and Linda gave me the cheque book and told me to buy a Tanzer 22 and to arrange for bringing her home. We did evenings and weekends for four summers. Got her fixed exactly the way we wanted. Took her on a ten day "vacation" and came home and sold her.
Bought a Tanzer 28. Did coast of New Brunswick and coast of Maine for seven summers. Got her exactly how we wanted her. Went on a eight week vacation on her, came home and put her up for sale. By then daughter was married and son was too.
Now we have a 34 foot Irwin. We will be doing close to three months on her this summer. I sure hope she is not for sale when we get home
We sold the house, moved into a townhouse where they do all the mowing, gardening etc.
Mu suggestion - do it slow, have fun. You can't follow the kids and grand kids cause they keep moving. I am sort of retired, Linda writes full time and as long as I make sure everything Linda needs is covered - we will enjoy the boat, the water and most of all each other.
The dream might be Tahiti, the Caribbean or the world. Reality might be a week, a month or a year on the boat at a time. Just because it comes in smaller time hunks does not mean it is not "cruising" (small c and in quotes)
It seems to be working for us - I pray it will work for you as well.
Rik & Linda