Live Small

Hundreds of sailboat designs compared on a triangle course:
http://www.ussailing.org/portsmouth/tables08/tables08mh.asp
A lower number is faster. Basically, in a race that a Sunfish(Portsmouth Yardstick 99) could complete in 99 minutes, a 49er(PY68.2) could finish in 68.2 minutes. The data is submitted from race results. That’s mostly on triangle courses where the bulk of time is spent beating into the wind. Thus it favors windward ability over top speed.
The Wikipedia Page explains how to apply the numbers in a real race. 
Among monohull centerboard boats, some are a lot quicker than the nearest competitors. 
For instance Frank Bethwaite’s very fast 16foot "49er" (PY68.2) with trapeze and wings:

Most of the other 49er-esque carbon/wings/trapeze/spinnaker things are around PY80.

There are some big "offshore classes" with fixed keels that are as fast, but here are a couple of midwestern monsters you won’t see at Nelson’s (a local boatyard):
The 38foot "A scow" (PY61)

The 28foot "E scow" (PY72.6)

The sunfish gets a rating of PY99, faster than a bunch of boats I thought would beat it.
The laser (PY91) is just a little faster, probably because the cool name attracts more serious skippers.
The Moth only gets PY107, which has to be wrong. That’s a racing class with hydrofoils and they’re very fast So don’t trust the list completely. There are many boats with the same name, that may be the source of the confusion.

The multihulls are all fast. The surprise is the Tornado (PY59), which is a 40-year old design with new sails, still within a few digits of the fastest. It’s interesting to see the comparisons between boats with the same hull and different sailplans, spinnakers, and trapeze added.

A buddy and I have one of these things in MA, but I’ve never sailed it. The centerboards are really wide and stubby.

The Malibu Outrigger (PY79) is a plywood outrigger sailing canoe inspired by craft seen by U.S. soldiers in the Pacific in WW2. Its performance is better than many high tech race machines. I would expect a true traditional canoe with equal weight, size, and sail area to perform as well or better. I rode a chase boat at a canoe race in the Marshall Islands, and we had to plane to keep up with the leaders. Here’s footage of the MH national race in 2001. Unfortunately these boats haven’t been submitted to the yardstick.