Faster Than a Contessa 26

[CarlF]

The only way to go faster than a Contessa 26 is to add waterline length. Your boat is reaching her hull speed in fairly light winds. A fin keel, lighter boat with the same waterline length wouldn't do better (except in very light winds). And the Contessa's weight is a real advantage punching into a sea in average winds.

And if you like the "feel" of a Contessa (as I do), a fin keel, light boat won't be the same.

To get a significant speed increase, I'd look for at least 4ft more waterline length than the 20' of the Contessa. This will mean a substantially more expensive boat but your day's run would be much better. What's that speed worth to you?

For similar feel to your Contessa but faster, you could look at:

Cape Dory 33
Sea Sprite 34 (Luder design, fractional rig so easy to single hand)
Bristol 35 (particularly fast)