Not U,
I'm only a toddler in the sailing world but I have grown an opinion in my two year tenure. After all, opinions are like eyebrows. Everybody has at least one!
My personal recommendation would be a large trailerable with a decent head.
Trailerable for flexibilty. You can drive at 65 MPH and reach foreign ports in hours not days. The draft would probably be less so you can get in areas that a larger boat would avoid. No fees for launching, stepping, storage or slip. The trade-off? Larger fixed keel boats probably handle better and the accommodations are more comfortable, but sometimes marginally. About the price. If a given trailerable at 25' was $6000 on the trailer, a 30 footer might be closure to $15000 (but look around).
The head? Make sure your bride likes it. It should be big enough to . . . . you know, without throwing out your back trying to reassemble yourself. It is quite a docking maneuver in my Lancer 25.
We haven't actually logged our trips (probably should thought) but I estimate that we have sailed 800 miles in two years in winds from dead calm to 35 knots. We've run aground, lost the dingy in heavy seas, been lost in fog, nearly lost the motor, lost the dingy prop (any pattern yet?), dragged anchor 4 times, paddled to shore with a dust pan duct taped to a boat pole, broke a winch off the coping, snapped all my mainsail slugs in a freshening breeze. To mention just some of the character of our trips. Yeah, it has been a blast, and a learning experience. But we've spent some great nights with the family, seen sunsets, whales, porpoises, seals, wild sheep and a host of birds that we would never have seen. There is nothing like a cup of hot coffee while relaxing in the cockpit on a cool morning. Or a cold beer as the sun sets over the mainland as the boat gently rocks to the swells. Boy am I running on or what?
To sum up in four words: "Big trailerable, nice john."
Fair Winds,
Don