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I have both boats presently, although I only have a couple dozen hours on my new Outrage 18. So far my impressions are the Outrage has a better ride, but not remarkably so. It is a bigger boat and has more room for people and gear. The canvas system is much better in my opinion, with better protection and more head room. The larger beam also allows one to walk past the console rather than shimmy.

I've almost 200 hours on my Montauk, and it is a great boat. The most I've had on are 6, but given the size you are crowded. I was just ferrying people around, not doing boat activities like fishing or crabbing. Mine is powered with a Yamaha F70 bought new in 2011, and even with 6 we were doing high 20s although of course it took longer to get up on plane. I was "all in" for $8k in 2011, including motor, controls, rigging, and tax.

For just your family I think the Montauk would be a fine choice. If you planned on regularly having more on board, you'll probably want something larger.

Dennis