The Monterey 255 SS 2020 vs Monterey 355 Sport Yacht 2017 comparison sits squarely in the category of decisions where specs alone won't tell the whole story — intended use, storage, and long-term ownership costs all factor in.
Both boats share a closely matched power ceiling — 350 hp for the Monterey 255 SS 2020 and 350 hp for the Monterey 355 Sport Yacht 2017. Real-world performance will come down more to which motor is actually bolted on, its load at the time, and whether it's a 4-stroke or 2-stroke setup. Fuel capacity breaks the other way: the Monterey 255 SS 2020 carries 65 gallons versus 21 gallons in the Monterey 355 Sport Yacht 2017. On a lake day that's negligible, but for coastal cruising or long reservoir runs the extra range matters.
For family outings this is probably the sharpest distinction between the two. The Monterey 355 Sport Yacht 2017 is rated for 10 passengers, while the Monterey 255 SS 2020 caps at 7. If you're regularly pulling extended family or a group of friends onto the water, the extra seats on the Monterey 355 Sport Yacht 2017 could be the deciding factor.
Bottom line: Choose the Monterey 355 Sport Yacht 2017 if your priority is putting more people on the water — it handles 10 passengers and at 35,3 ft it has the deck room to back that rating up comfortably. The Monterey 255 SS 2020 is the smarter pick if you want a lighter, easier-to-trailer boat rated for 7 that costs less to run day-to-day.