How big of a boat?

Fitz, Many years ago I was right in the exact same spot you are now in. I had a 20' bowrider and wanted a larger boat. I didn't want to buy an in-between boat, I wanted to do it in one step.

I looked at and drove a 310 Sundancer. Liked the boat but found I could not stand up straight when I was in the cabin due to lack of headroom.

I ended up with a 330 and slipped it. I didn't own a tow vehicle when I wanted to move it around so I rented a 3/4 ton F350 from Budget Rentals. Doing it that way saved me from having to buy/insure/license a tow vehicle.

As to picking the right boat, I was the one who came up with the idea of "Buy your second boat first". By that I mean that many people want a bigger boat so they pick the first one that blows their hair back. They own it for a year or two then want to trade it or sell it so they can get the boat they should have bought first. Owning a boat for a couple of years and wanting to sell it is VERY expensive.

So, take your time, look at lots of boats. Take your whole family and put them on board, then picture that boat with a couple of extra friends on board and see if the boat will fit your needs. You didn't mention how many kids you have or how old they are now, but try to visualize the boat in a few years when the kids get older, their legs get longer, and they always want to bring a friend or two when they're on the boat.
 
Adding my two cents, if you are interested in going to MV or block island then you want to keep it on the cape or buzzards bay. The trip through the canal is too long to do regularly. We live just outside of boston and keep our 310 DA in marion on a mooring. Great location for heading out to the islands. I will add however that buzzards bay gets snotty in the afternoon and anything smaller then a 310 can get knocked around pretty good. We find that our 2000 310 which is 33 feet long, was the right combination of price, room, and economy. We do not have a generator and would not recommend it for this boat. We regularly take the boat to the beach, weekend or week for family of three plus a friend for my daughter. This definitely not a boat you can tow though.
 
My wife and I moved up from an 18 ft run about to a 2001 380 sundancer. We loved the boat and it is great space for two people to spend weeks on if you would like. We moved up to our 40 sundancer since we learned that how we boat diesel power, hydraulic lift, and a hard top where must haves. There is a lot of truth to buy the biggest boat you can. Not sure of the $$ you are looking to spend but there are a lot of great options in the early 2000 range. As others have mentioned slip the boat it is worth every penny (and we have high prices at $200 per foot)

 
We do not have a generator and would not recommend it for this boat. We regularly take the boat to the beach, weekend or week for family of three plus a friend for my daughter. This definitely not a boat you can tow though.
Boston, I respectfully beg to differ with you on (a) not having a generator and (b) the towability of a 33' boat.

I towed my 330 several times, the longest trip was 300 miles each way from home to Anacortes, WA. It included going over the Cascade Mountains' 3000'+ Snoqualmie Pass, through rush hour traffic in the Seattle area, etc. It takes some planning, the proper permits, and a suitable tow vehicle and some huevos. Easy tow? No. Impossible? No, you just have to think ahead, plan ahead, and take your time.

As far as a boat that size without a generator, that really hurts the resale value. That size boat is meant to overnight on. That usually means having power for a few days and that usually means a generator because batteries alone won't do it. Sea Ray did build a bunch of boats the dealers called "Lake Boats" that were built with no provision for a genset. It's my understanding they did not sell all that well and SR discontinued building them.
 
If you would like to see a 280 I am about an hour from you. Regarding the other subjects, I do keep the boat on a trailer pull it in and out every time I use it. I don't like the idea of having sterndrives sitting in saltwater for a season if I can avoid it. when I go out it is generally with 6 people total, two young kids and four adults. The two kids sleep on the dinette, two adults in the aft cabin and two adults up front. I did buy an F-350 I also plow with it but the size of a truck was primarily because of the towing the boat. My drive from the house to the water is about an hour. A weekend out on the boat goes something like this, Friday after work hook up the trailer and make sure that everything I want on the boat is. My wife and daughter do all of the other (food water etc) loading. Saturday morning leave around 7ish . Pull it out of the water Sunday night and usually be home around 8-9. Next day spend about 2 hours cleaning. I am a mechanic by trade and I love everything with engine(s). Having the boat at my house makes it easy to tinker with it whenever I want. Even with 6 people I don't want a bigger boat, 16 - 18 GPH fuel burn, small 4.3L engines, simple alpha drives but big enough to be completed self contained for a weekend if you want. Being able to handle the sea? Any boat will have its limits. I hear vessels with steel hulls do good:p
 
A few thoughts. We keep our 340DA on a mooring in Mattapoisett, and the comment about Buzzard's Bay getting snotty in the afternoon is an understatement. I had a Sea Ray 230 cuddy before, and in the morning, we'd fly over to the Vineyard and it was like glass. Coming home in the afternoon across Vineyard Sound, and then thru Woods Hole and back through Buzzards Bay was not always so fun... We'd hole up in Hadley's Harbor for a while until things layed down around dusk before coming across. "She who must be obeyed" loved the ride in the morning, hanging out at a beach, poking around shops in Oak Bluffs or Vineyard Haven, but I dreaded the ride home, knowing I was going to hear about how rough it was... The 340DA now allows us to slog thru the Buzzards Bay chop most afternoons without too many complaints, and if it's bad, we have plenty of room to stay for a night or two in reasonable comfort. Still, there are afternoons that it's not enough boat to keep everyone happy. When it's rough out there, it can seem like no boat is big enough for some. I guess my message is that with the 23' boat, we had a lot of fun, but there were many days we just stayed in our little harbor and had a cocktail. (Not that there's anything wrong with that.) With the 34', there are a lot more days and weekends that we take off without worrying about it being uncomfortable. I like the advice people have given about actually getting onboard as many boats as you can, get a feeling for them before you buy. We have a 2002 340DA, and that kept the price more reasonable. If we tried to get a 2015... well, we'd be buying a 23 footer again probably!
 
We bought our 1st cruiser in June of '14-260 DA w/ gen on a tandem axle aluminum I beam trailer. We keep it at home in a shelter that was built specifically for it. I pull it with a '07 Silverado Duramax/Allison. We pull it either west or east about 1.5 hrs to one of 4-big lakes most every weekend and holiday from April-September. It is perfect for the two of us and I could see adding a smaller child and having enough room. Adding more than that-too smali to overnight. We have a gen and love to stay on the hook. As mentioned above, keeping it at home has allowed me to add many extras and more conveniently, work on it. It has served us well and we have had a lot of fun. We are starting to look and learn about the sedan bridges and motor yachts and have spent some time on a '08 44 SD. We are a few years away from pulling the trigger, but this will be our next and last step into a boat like this docked on a fresh water lake and used as a 2nd home.

I am glad and do not regret owning the 260. As I do most of my own maintenance, thanks to the people here, it has served to acclimate my wife to boating and financially, been very easy all things considered. It has also helped us to understand the difference between the "wants" and the "must-haves." Hope is helps.

Bennett
 
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I grew up on Cape cod and know the waters well. We used to have a 27ft boat and got caught trying to run back from MV to Falmouth and it was a brutal ride with rough seas and lobster pots everywhere. The wind channels through the sound and turns up the water real quick. I like the advise that a larger boat would be better and maybe go a few years older. Also being on the boat stuck at the marina is more fun than being at home looking at your boat that could be in the water.


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Final comment on trailer vs marina.

As mentioned I live in Central MA, 35+ years ago my parents bought a summer house in Mattapoisett so I spent the majority of my youth there on weekends. I can't count the number of times we would come home after a weekend and have everyone complain how crappy the weekend weather was here in central MA, and yet only 1.5 hours away we had a beautiful weekend. If your boat was in a Marina you may be more inclined to head down even if weather at home is marginal to discover its beautiful on Buzzards Bay and the islands.
 
agreed with hanging at the marina. on friday evenings after work we would head down to the marina and just hang out on the boat for a few hours. we only started the engine on fridays maybe 2 or 3 times since we slipped it in early july (we bought it early june but it rained like crazy till the end of the month). i would venture to guess we put less than 10 hours on it all summer as we hung out at the dock most of the time. if we trailered it we would have never been there on a friday night
 
Also so I would never slip an IO in salt water - NEVER. ask me how I know.
my I/O has been in salt water all but 2 years of its 18years on this planet...care to elaborate why the majority of boats i see IN salt water should never have been placed there?

i'm just south of Boston at a Yacht club this year (followed advice from hottodie). we made the hefty, costly mistake of going to a marina our first year as "non trailer boaters". what a waste of money. for $5200 i rented a spot. a great spot, but just a spot. next to nothing for services, next to nothing for security, next to nothing for parking or concern from management about my money or investment. and service staff that always looked like they couldnt wait to take advantage of you. Trash was never cleared from the dock (we were on a river leading to boston harbor down stream from a dog park hundreds of tennis balls a month were against the dock, dead birds, sticks, trash, plastic cups......).
I had great dock neighbors and a lot of great memories but nothing i'm glad i'm not going back.
That said, nothing compares to showing up to your boat already on the water, ready like you left it. hanging out on the boat instead of trailering home, sleeping on the boat instead of driving buzzzed...
i have the biggest 290 searay made, i believe. just at 30' with over 10' of beam. it is great in bigger water but with 6 people on board it gets tight quick. we have had well over double that number but you run out of room very fast as nobody wants to hang out below deck.
we have family down the cape on the water in Falmouth so ours heads down there in summer too but it wouldnt be an enjoyable ride in anything smaller. we plan on heading to Block this summer for at least a few days too.
buy a big boat now and cry once. instead of upgrading later and crying twiice
 
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