The Monterey 255 SS 2020 vs Monterey 258 SS 2019 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.
On paper these two are close siblings in the size department — Monterey 255 SS 2020 at 25,8 ft versus Monterey 258 SS 2019 at 25,1 ft. Weight tells a clearer story for trailering families: the Monterey 255 SS 2020 tips the scales at 5 500 lbs — 400 lbs more than the Monterey 258 SS 2019 at 5 100 lbs. That difference is meaningful if you're working within a half-ton or three-quarter-ton truck's tow rating, especially once you factor in a motor, gear, and fuel.
The power gap is worth calling out. Rated to 430 hp, the Monterey 258 SS 2019 has a 80-hp advantage over the Monterey 255 SS 2020's 350-hp ceiling — enough to notice on acceleration and at cruising speed, particularly with a full passenger load. Both carry nearly identical fuel loads — 65 gal and 65 gal — so range won't be a tiebreaker here.
Both boats are rated for 7 passengers — a good fit for a family of four or five plus guests. Comfort at capacity is another matter; the longer hull typically means more seat options and better weight distribution.
Bottom line: Performance buyers should lean toward the Monterey 258 SS 2019 and its 430-hp ceiling. If fuel economy and quieter running matter more than top-end speed, the Monterey 255 SS 2020 with its 350-hp rating is the more economical daily driver.