Writing on the wall
After 23 years of sailing I am now faced with the same problem. Three years ago I upgraded to a legend 37.5 (replacing my H31, that I raced all the time) and have all the comforts of home for the family. It is now my floating condo, no one wants to sail much anymore, and certainly not race. I have sailed less and less each year. I sold my R.I.B, and bought a Boston Whaler Supersport (can be towed, SLOW)and it gets used all the time, we can go to the beach, fishing, exploreing etc... And now my son is always showing me pictures of fast boats with (2) engines, thats what he wants, and my wife agrees (although she likes Dock Life). What is a diehard sailer to do? I started boating with small powerboats, but had always wanted to sail. I told my wife, I'll buy it, you feed it, and her comment was "then we will stay at the dock", and I said "thats what we do now , so why buy another boat". We sail Buzzards bay, so a heavy duty roughwater powerboat with deluxe accomadations would be needed (alot of $$$$$$$$$$) I am considering replacing the Whaler with a bigger Whaler (21 to 23feet) with a cuddy cabin for day trips, and keeping my sailboat (I still want to race to Bermuda). More Money???? The way I figure it, I made the situation worse by buying the whaler. Maybe I should buy that 38' mainship with the twin diesels, and get it over with. Oh well.