The Crestliner Grand Cayman 2385 2009 is a pontoon design and the Crestliner Retriever 1546 DS 2012 is a modified-V design, so you're likely deciding between two noticeably different on-water experiences. Hull type shapes everything from ride quality and fuel burn to dock handling and resale trajectory.
Size is the most obvious dividing line here. The Crestliner Grand Cayman 2385 2009 measures 22,0 feet overall (2009), giving it roughly 7,0 additional feet of deck space compared to the Crestliner Retriever 1546 DS 2012 at 15,0 feet (2012). Weight tells a clearer story for trailering families: the Crestliner Grand Cayman 2385 2009 tips the scales at 2 150 lbs - 1 650 lbs more than the Crestliner Retriever 1546 DS 2012 at 500 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 150 hp, the Crestliner Grand Cayman 2385 2009 has a 110-hp advantage over the Crestliner Retriever 1546 DS 2012's 40-hp ceiling - enough to notice on acceleration and at cruising speed, particularly with a full passenger load.
For family outings this is probably the sharpest distinction between the two. The Crestliner Grand Cayman 2385 2009 is rated for 12 passengers, while the Crestliner Retriever 1546 DS 2012 caps at 3. If you're regularly pulling extended family or a group of friends onto the water, the extra seats on the Crestliner Grand Cayman 2385 2009 could be the deciding factor.
Bottom line: Choose the Crestliner Grand Cayman 2385 2009 if your priority is putting more people on the water - it handles 12 passengers and at 22,0 ft it has the deck room to back that rating up comfortably. The Crestliner Retriever 1546 DS 2012 is the smarter pick if you want a lighter, easier-to-trailer boat rated for 3 that costs less to run day-to-day.