Gulfstream shopping.

As you are in Westchester, Mystic is not really that far to do a sea trial and see for yourself if the 225is enough for your use case. Can always catch a good meal in any event. Can’t hurt to try anyway.
 
I have owned a 2006 232 for the last 20 years, I bought it new and just sold it a few week ago. It had twin Yamaha 150's which ran beautifully for that boat. As a data point, I was off shore about 5 miles and had an issue with one of the engines, so i returned on the single 150. We had 4 folks onboard and I assumed that the boat would run fine on the single but was surprised to find that I was unable to get up on plane with the single 150 hp engine. My recommendation would be to go for the twins, I have never had a single on that boat but the twins run great. As mentioned, test ride the boat, more HP is always better. As far as pricing, from the analysis I did the boat sells for mid to upper $40's. I saw some re-powered 232's in the low $50's. Good Luck!
 
I have a 1989 GW Sailfish with twin Yamaha 150s. I'm in Virginia Beach so fish and boat on the Chesapeake Bay and close off shore. I know the Gulfstream is 2 feet shorter than my Sailfish but, I can say without hesitation, having twins is paramount. I believe they are similar in height above water so I would expect the Gulfstream to be a "sail boat" in high winds. I'm certain I would not have been able to control the movement of my boat in the wind without twins. There were times, even with twins I was, somewhat, out of control due to the wind.

My parameters when I was looking for a boat were: I wanted two engines but the boat could plane on one. My boat, even with the motors being so old, can, barely, plane on one. I also wanted two separate fuel tanks and two independent batteries. And, "unsinkable"?

I have had single engine boats in the past. I would not want one now. That said, they were both much smaller, less mass, boats so could be maneuvered with one engine fairly well.

But, I would like to re-power my boat! Probably to 175s at most.
 
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To each his own. If you can't control a single engine boat, definitely get twins. I have zero issue maneuvering my 232 with a single screw.
 
I have a 1989 GW Sailfish with twin Yamaha 150s. I'm in Virginia Beach so fish and boat on the Chesapeake Bay and close off shore. I know the Gulfstream is 2 feet shorter than my Sailfish but, I can say without hesitation, having twins is paramount. I believe they are similar in height above water so I would expect the Gulfstream to be a "sail boat" in high winds. I'm certain I would not have been able to control the movement of my boat in the wind without twins. There were times, even with twins I was, somewhat, out of control due to the wind.

My parameters when I was looking for a boat were: I wanted two engines but the boat could plane on one. My boat, even with the motors being so old, can, barely, plane on one. I also wanted two separate fuel tanks and two independent batteries. And, "unsinkable"?

I have had single engine boats in the past. I would not want one now. That said, they were both much smaller, less mass, boats so could be maneuvered with one engine fairly well.

But, I would like to re-power my boat! Probably to 175s at most.
It's not realistic to expects a boat setup for twin engine to plane on a single engine. It's not prop'ed correctly and it's a strain on the motor.

I have a 268 Islander which is basically a narrow beam Sailfish with twin F150's. The boat has always been difficult to maneuver/dock even in a 5 knot crosswind. I have never been able to "turn" the boat with my engines. Maybe it's because they are so close together...I don't know. My solution was to install a bow thruster. That turned out to be the best investment in my boat I ever made.

IMG_0531.jpeg IMG_0505.jpeg
 
Couple of threads that discuss bow thruster install.


 
I have a 1989 GW Sailfish with twin Yamaha 150s. I'm in Virginia Beach so fish and boat on the Chesapeake Bay and close off shore. I know the Gulfstream is 2 feet shorter than my Sailfish but, I can say without hesitation, having twins is paramount. I believe they are similar in height above water so I would expect the Gulfstream to be a "sail boat" in high winds. I'm certain I would not have been able to control the movement of my boat in the wind without twins. There were times, even with twins I was, somewhat, out of control due to the wind.

My parameters when I was looking for a boat were: I wanted two engines but the boat could plane on one. My boat, even with the motors being so old, can, barely, plane on one. I also wanted two separate fuel tanks and two independent batteries. And, "unsinkable"?

I have had single engine boats in the past. I would not want one now. That said, they were both much smaller, less mass, boats so could be maneuvered with one engine fairly well.

But, I would like to re-power my boat! Probably to 175s at most.
that seems severly underpowered. even if you went up to 175s.

my chase has twin 250s and it feels right.
 
I just wanted to reply with I run a 248 with a single Yamaha 225 in Hawaii, I could never try to go on plane on the water here, 12 knots max on the best day due to ruff seas here, so with that said twins do make it easier for maneuvering around docks ( we don’t have marinas here either, every day they have to be removed from the water )and I find that my F225 works for me here just fine so you have to determine what conditions you are dealing with at your location. But for safety twins cost more to run but you have added safety of 2 motors to get you home if you don’t keep up with your maintance