Hey Rich, first of all that's a great picture of your boat!  I am under agreement for a 1999 C36 MKII, I take delivery in May after the surveys are complete.  Since I am new to Catalina and have never owned a boat this size before I can't speak with authority, but just a couple thoughts... 

If it's just you and your wife primarily cruising, why the need for the bigger boat?  I like the idea of upgrading your existing boat with more "creature comforts".  What kind of electronics do you have?  Upgrade the chartplotter and radar if they are outdated. Install a NMEA 2000 backbone and then plug and play with the latest and greatest.  Hows your auto pilot?  A below deck auto pilot is a nice upgrade to do at the same time you do the new chartplotter and radar.  A below deck autopilot is more reliable and can act as emergency steering (when underway and away from any real steering requirements).  TracVision would be a nice addition to the salon for sure.  What about your AC and heat?  Already have it?  How are your batteries arranged?  Have a decent bank?  Solar charger?  Recent bat charger?  Charger/inverter?  How about the head... have you converted the sea water head to fresh?  I also saw on this forum a guy who had added a splitter to the fresh water supply line going up to the sink.  He converted the sink faucet to a permanent one, and led the other side out of the cabinet to a line going up to a proper, full-time, hand held shower head that stayed on it's hook.    Finally, what about changing out the spar for in-mast furling?  

Let us know when you head up to Cape Cod, it's a true sailors playground, lots of great places to gunkhole!  Safe sailing!

Mike

under-agreement, 1999, C36, MKII, Tall, Wing, In-mast
Phinney's Harbor, MA

This is a perfect boat for two.  The previous owners went back and forth between Annapolis and Stuart, Fl.

Since you are on the East Coast, make sure to watch the draft.  If I remember correctly, the 400 came in @ 6’.  Under 5’ will keep you out of a lot of trouble.  My wing keel is 4.5’.

If it ain’t broke ... don’t fix it.  :)

Hi Neighbour-across-the-lake!  I've not done your planned trip, but know several C36 owners that have without complaint. I would suggest that you have a perfect boat now for such a cruise: (1)  A Catalina 36 is an ocean-going vessel, perhaps not bluewater, but certainly coastal cruising.  The bluewater difference is the length of time sailing (chafe and wear) and the ability to handle higher-strain weather (there is no harbor you can reach in 24 hours).  Adding another two or four feet of length will not alter seaworthiness.  (2) The Great Lakes are ocean-like, except for distance from shore.  Our winds reach Storm and even Hurricane forces during thunderstorms.  Our wave periods are much shorter than the ocean waves.  You get much more of a pounding in a Lake Huron chop than a rolling swell in the Atlantic.  If you're comfortable with the size of your interior, then why increase your costs by adding to it. Have confidence in your boat.

As far as fixing the shower - that's a maintenance issue best solved with some 3M 4200 (never silicon!) from the side the water is originating on.  Make sure everything is dry first, say right after winter storage.  Shine a light from the other side to spot gaps.  Also, consider adding some thin weatherstipping to the bottom of the door as there can be a 5mm gap under there.

V-berths can be improved by adding the Froli system springs underneath for $320 and an afternoon of snapping together plastic things - ​https://www.catalinadirect.com/index.cfm/product/4193_1566/span-style-froli-bed-spring-retrofit-c-34-c-36-v-berthspan.htm  If that's not enough, you can invest in a custom V-berth matress, but that will cost what a household king would, so $2-3,000.  I've never cruised long enough, or had a bad back, to make that worthwhile.

It appears that you already have davits mounted, so I assume you already have a nice dingy for this trip, which is good.  By the way, I absolutely love cruising your coastline and the warm welcome we get at the harbors!

We don't have "seepage through the wall" when using the shower, but we did have issues with it getting under the door.   The solution was adding an angled block of teak across the bottom of the door on the inside to divert the water into the shower pan (this might have been one of the jillion good ideas lifted from Tom Soko -- see https://julandra.shutterfly.com/180  We also modified the shower with a seperately plumbed fitting and hose, similar to what Tom did. https://julandra.shutterfly.com/211  https://julandra.shutterfly.com/214  When cruising, we also carry a couple of solar shower bags (which you can get from camping suppliers), which we will rig up to showers either over the hatch for the head or in the cockpit; they work great, especially if you haven't motored for a couple of days and thus have no hot water in the tank.

As to your plan to "spend a summer on the east coast, Annapolis to Cape Cod. I hope the boat is a decent size for this. (I need convincing)"
I think the boat is certainly large enough in terms of its sea-worthiness for the areas you intend to go and the type of conditions you'll encounter.  We've sailed ours from New York to Maine and back 4 times, and it always felt fully up to the task, including overnight ocean passages.   We've also found it very comfortable for 2 people during an extended cruise  (but that's always a matter of taste -- we once had 9 adults aboard for a 4 day weekend to Block Island, lots of fun, but not great for a long haul!)
 

AS Mathew said you need to see what Tom Soko did to his boat.My wife looked at his boat and I had projects for a year.but made for a much nicer and more comfortable boat