28 or 32 foot advice

Anytime you are on the fence between bigger vs. smaller, go bigger. Boats tend to shrink when wet, and if you are even considering bigger now, you will be absolutely requiring it in a year or two.
 
I have recently sold my 20’ bow rider and want to move up to a cruiser. Currently looking at a 2006 28 Sundancer, single engine or a 2006 32 Sundancer, twin engines. I don't plan on pulling tubes and will be cruising the upper Chesapeake Bay. Any advice on the better choice.
It really depends on your budget and the room you will think you'll need. Going from 1 engine to 2 is nice for the ride and dependability to get home, but you will burn more fuel as well as double the maintenance. I went from a 1990 27DA single engine to a 37DA with 2 inboards. It was definitely more maintenance and fuel consumption,.....but what a ride.
 
I can't add much to what everyone has said, but here is my story. I owned 19' Chaparral bow riders for 25+ years. Great boats and raised the family with it doing water sports/recreation. Kids are now in college/grown, and so my wife and I wanted to try a cruiser. We went with a 2001 310DA as a "test" boat. I doubt we'll keep it more than 5 years, so didn't want to put down too much money. If we love this new type of boating, we'll go bigger; if not, we didn't break the bank. Bottom line: the problem with the "buy your 2nd boat first" advice, which I totally understand, is that when switching to a different style of boating, you really haven't figured out what exactly you do want and what things are more important than others. Is it cabin size, maintenance costs, maneuverability in a marina, cost of purchase, etc. So, if you are really on the fence, you might consider an older one, and once you've figured all that out, then your 2nd boat will be (closer to) the perfect one for your new situation.
 
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Are you only going to be boating the Chesapeake Bay? The 280 is certainly more mobile, if your plans are to have it moved around the country. If you are staying in Chesapeake, I would think the larger boat is the way to go on this one.
 
When we upgraded from our Maxum 270, we were shopping for a 320 and ended up with the 340. The 2 feet did make a difference. The 320 is a great size boat, engine room is tight if you do your own maintenance and go with V drives. We have outdrives on our 340, but we also moor under cover and on a lift. Engine room has tons of room with the out drives. Go with what suites your fancy. As said above - very fee, if any, have regretted going bigger. Good Luck.
 
We have a 240DA. It was our starter cruiser from being in an open bow day boat. We love our boat and it is usually just the wife and I. We still aren't ready to slip and forget. We have friends all over the place. So we wanted a trailerable boat. But, docking in high winds with a single engine boat is hell! We played pinball a couple times last year. Our next choice will be moving up from an F150 to a F450 and a 320DA for space, almost certainly a genny and twins for manuevering.
 
We have a 240DA. It was our starter cruiser from being in an open bow day boat. We love our boat and it is usually just the wife and I. We still aren't ready to slip and forget. We have friends all over the place. So we wanted a trailerable boat. But, docking in high winds with a single engine boat is hell! We played pinball a couple times last year. Our next choice will be moving up from an F150 to a F450 and a 320DA for space, almost certainly a genny and twins for manuevering.
That 240 is pretty much the perfect boat for a couple spending a day and maybe one night on the water, in my opinion. Not too small. Not too big. Easy to trailer. Easy to park. Sort of like the quad-cab 1500 pickup of automobiles. Should be easy to sell when you list it.
 
I would like to have gone bigger originally but the slip fees and price of the boat were more than I was willing to let go. As it turns out, I'm really loving my 2005 280 with twin engines. It's actually 31' long. I only sleep 4 (2 adults, 2 middle school kids) though and that's really all that's going to be comfortable unless it's the spring/summer evening outside is comfortable. The model does have a full enclosure but the previous owner apparently (accidentally) ripped off the zippers so it won't fully enclose.

I don't go with "spend as much as you can". You never know what add-ons you want to play with and what other things in life will come up, be it vacation opportunities or unforeseen issues. Many boats have been repo'd and sold in auction. You'll enjoy the boat more if you aren't the least bit worried finances. ha

Who knows. If I can get the kids off to college and have done the other investments I want, then I may go larger some day.
 
Thanks to all that replied. I have decided on the 32 foot. I have found a beautiful 2006. The survey is scheduled for the end of the month.
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When I started looking to upgrade my bow rider to a cruiser, I started looking at the 280's (size and popularity) and then found a 310DA - 08. It's bigger and more spacious. If you are planning to spend anytime in the cabin. We had 3 adults and 2 kids for a couple of nights and it was a bit cramped but ok and manageable (smaller cabin would have been harder). Here is something I stumbled on and became an important part of the research, the 2008/09 engine models started having DTS. Boat handling is better especially when moving from single to dual engines (you don't have throttle and shift cables). you can sync the engines when cruising, which is awesome as it keeps the RPM in sync. this was one of many reason choosing the 310 over the 280. regardless, Searay was the cruiser brand I was buying.
 

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