Time for a new boat,

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Depending on weight / size, 10' beam can be DIY trailered given an adequate truck. You'd just likely need to obtain permits before moving it.
 
I agree with this advice. If you can forgo the trailer you can get something in the low 30' range that will serve your boating goals much better. You'll never regret buying a little bigger boat than you think you need, but you will almost always regret buying a smaller one. Your budget allows a wide range of options if you don't need to trailer it.

Good advice! In 2017 I bought a 2013 Cutwater 28. We really liked it. It was easily towed behind my F250 (not dually). We quickly decided we needed a bigger boat and sold it in 2019. The 8.5ft beam is great for towing but not so great for stability. She tends to rock with the slights wake/swell. Maybe consider the larger Cutwaters and Ranger Tugs that have a 10ft beam and are still trailerable. You might need towing permits but if you're not towing that much it may not be a problem. You would need a larger towing vehicle or you could hire a truck and driver as suggested in a previous post. Be aware that a triple axle trailer will add a good bit of maintenance.

I found the Cutwater to be a quality boat and even though I bought it used, their customer service treated me like I bought it new. There is also a really good owner's website for Cutwater and Ranger Tugs (Tugnuts.com). The only negative was the gelcoat finish. My boat was ruby read and the glass pattern was showing through and there were areas of white speckling which would not buff out.
 
Sure do like the R29. Looking in that direction.
 
Sure do like the R29. Looking in that direction.

Unless I am misunderstanding, you are downsizing from a previous boat? What did you have before? I kind of chuckle at times to those who think trailering a boat saves a lot of money. They then need to buy and maintain and drive a good sized truck all year for the handful of times they trailer a boat. There is also the cost and maintenance of the trailer, registrations, etc. Portland to the San Juans is not that far or difficult of a cruise. Why not decide you will never trailer (unless you need to hire a transporter to move the boat) and put that money toward the boat? If your max budget is $200K, there are plenty of great boats in the 30-34' range that could comfortably handle that trip and also be much more comfortable every time you use it for entertaining or sleeping. Always smarter and less expensive to buy the bigger boat now than a few years from now. An R29 may look like more than enough for what you need, but I bet before the end of the season, you'll be thinking about the R31. Kind of like buying that 55" TV that looks plenty big in the store. After watching it a few weeks you'll be saying, I really should have bought the 65".
 
Unless I am misunderstanding, you are downsizing from a previous boat? What did you have before? I kind of chuckle at times to those who think trailering a boat saves a lot of money. They then need to buy and maintain and drive a good sized truck all year for the handful of times they trailer a boat. There is also the cost and maintenance of the trailer, registrations, etc. Portland to the San Juans is not that far or difficult of a cruise. Why not decide you will never trailer (unless you need to hire a transporter to move the boat) and put that money toward the boat? If your max budget is $200K, there are plenty of great boats in the 30-34' range that could comfortably handle that trip and also be much more comfortable every time you use it for entertaining or sleeping. Always smarter and less expensive to buy the bigger boat now than a few years from now. An R29 may look like more than enough for what you need, but I bet before the end of the season, you'll be thinking about the R31. Kind of like buying that 55" TV that looks plenty big in the store. After watching it a few weeks you'll be saying, I really should have bought the 65".

Agreed, Looking for something that will slip into the smaller moorages here in Portland. My current boat is 51' and that doesn't slip into the spaces we have. Much better around 30
 
Investigate Stabicraft out of New Zealand. They are poplar with the emergency services there, and having piloted my 20’ from Roche Harbor to Ketchikan I can see why. It is reassuring to have a boat that is eager to take on more than you yourself might want to. Besides being SAFE, they are extraordinarily low maintenance and light enough to trailer easily. The lager models offer enclosures perfect for the PNW climate. I think you might be surprised.
 
New Boat

That is correct, day cruise four adults only. Overnights w/ only my family which is my wife and son of 11. One of the reasons I am drawn to the Cutwater/Ranger Tug line. Yes small accommodations for my son but it will work for sleeping.

Actually, for what you are talking about, the Ranger Tug 25 would work. It would save you a lot of money, be easier to tow, cheaper to berth, cheaper to operate etc. I have a C Dory 22 as well as my GB 36 so I'm a fan of C Dory's but the 25 Would be pretty cramped for your needs.
 
Ok so we bought a vacation property that has us out of town quite a bit now, great way to be Covid safe. However, I still need a boat and am going to down size. Something I can handle by myself so I can take clients around Portland. Needs to house four adults for a cruise, be comfortable at all times of the year, (enclosed), at least do 20 knots when we don't have trees coming down the Columbia, under $200k, small enough we can get into any marina so no more than 30 feet. Preferably trailerable to take up to the San Juans once or twice a year. Boats I have looked at am interested in,
25/26 C-Dory
27' Ranger Tug both inboard and outboard
28' Cutwater
25' Rosborough
I don't care much for the high powered fishing style boats as I feel they lean more towards fishing than cruising.

Other boats I should be thinking of?

Having read your requirements, and all the other posts to date, I wonder if your brief might not be met best by doing what someone else suggested on some other thread.

Buy a MacGregor 26 trailerable sail boat, which has water ballast that can be dumped for trailering, and is not over-width or too heavy to tow with a reasonable sized car or SUV. They have an outboard through the floor of the cockpit that allows for 20kn plus when light and not rigged for sail. Lifts up out of the water to sail.

But if you didn't want to bother with sail, one person commented that with the rig removed it still made a roomy and very fast, yet seaworthy boat, (with ballast on board), and they are certainly set up for family cruising.

Hey...not a trawler, but what is..? But if you want something light to trail, roomy, practical, seaworthy, suitable for over-nighting, and capable of some speed, why not buy one designed for exactly that..?

https://www.bing.com/images/search?...CD61A3&selectedIndex=7&FORM=IRPRST&ajaxhist=0
 
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