The Oyster Yachts 55 1986 vs Oyster Yachts 595 2020 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.
Size is the most obvious dividing line here. The Oyster Yachts 595 2020 measures 62,6 feet overall (2020), giving it roughly 6,2 additional feet of deck space compared to the Oyster Yachts 55 1986 at 56,4 feet (1986). Weight tells a clearer story for trailering families: the Oyster Yachts 595 2020 tips the scales at 67 918 lbs — 16 925 lbs less than the Oyster Yachts 55 1986 at 50 993 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 Oyster Yachts 595 2020 tops out at 150 hp. Engine specs for the Oyster Yachts 55 1986 aren't listed — confirm with a dealer before selecting an outboard.Fuel capacity breaks the other way: the Oyster Yachts 595 2020 carries 355 gallons versus 159 gallons in the Oyster Yachts 55 1986. 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 Oyster Yachts 595 2020 is rated for 19 passengers, while the Oyster Yachts 55 1986 caps at 17. If you're regularly pulling extended family or a group of friends onto the water, the extra seats on the Oyster Yachts 595 2020 could be the deciding factor.
Displacement is where these two sailboats genuinely part ways. The Oyster Yachts 595 2020 displaces 67 918 lbs — a 16 925-lb difference over the Oyster Yachts 55 1986 at 50 993 lbs. That gap separates two entirely different categories of sailing: the heavier boat is built for offshore passage-making and load-carrying, while the lighter hull rewards performance sailing and easier handling in lighter air.
Draft is a practical consideration that many buyers underestimate until they're already at the marina. The Oyster Yachts 55 1986 draws 7,6 ft, compared to 5,1 ft for the Oyster Yachts 595 2020. That 2,5-foot difference affects which anchorages you can access, which haul-out facilities will take you, and how carefully you need to read the tide tables in shallower cruising grounds.
The Oyster Yachts 55 1986 uses Cutter rigging. The Oyster Yachts 595 2020 has a documented auxiliary engine of 150 hp.
For extended cruising, water capacity matters: the Oyster Yachts 55 1986 carries 291 gallons versus 265 gallons on the Oyster Yachts 595 2020 — a significant advantage on longer passages where watermaker or provisioning stops aren't guaranteed.
Bottom line: The Oyster Yachts 595 2020 is the offshore and bluewater choice — at 67 918 lbs displacement and 63 ft it has the load capacity, range, and seakeeping for extended passages. The Oyster Yachts 55 1986 at 50 993 lbs is the more nimble, accessible option — easier to single-hand and better suited to coastal and inland sailing.