Buyer questions
Eight questions buyers ask about the Robalo 266 Cayman SD, answered from the boats listed on US Marine Connection right now.
Right now US Marine Connection shows 3 priced 266 Cayman SD listings, all with photos, asking between $189,938 and $205,697 with a median of $192,003. Those are asking prices, not recorded sale prices. Worth noting the three on the site are 2026 and 2027 boats described as new or in stock, so they sit at the top of the range rather than reflecting older used examples.
The current listings cover model years 2026 through 2027, across three boats. There are no older model years on the site at the moment, so if you are hunting for an early used hull you will not find one here today. The descriptions for the 2027 boats talk about in-stock inventory, including one finished in Alloy Gray with a Harbor Mist cockpit.
None of the three 266 Cayman SD listings states an engine hour figure, so there is no typical number to quote from this site. What the listings do show is model years 2026 and 2027, with descriptions written around in-stock, current-year boats. If hours matter to you, ask the seller directly for a reading from the engine display or service records before you commit.
Since these are 2026 and 2027 boats with no hours listed, start by confirming actual engine hours and whether any warranty is still in place. On a bay boat like this, check the hull bottom and running surface, livewell and bilge pumping, and that the hardtop hardware is tight. The descriptions mention an enclosed head, cushioned seats, rod holders and the second station, so test those and the upper helm controls yourself.
From the listing descriptions: an elevated bow casting deck that transitions to wide gunnels, cushioned seating, an enclosed head, and rod holders and storage compartments built into surfaces throughout. The SkyDeck name comes from the second station above the console, which the seller describes as a high vantage point for navigation and fishing. One 2027 boat is listed in Alloy Gray with a Harbor Mist cockpit and a white powder-coated fiberglass hardtop.
That is exactly how the listings frame it. One description has the boat working a grass flat at sunrise, running out to the Gulf of Mexico for a nearshore bite, then anchoring at a sandbar with the family. Another mentions inshore and nearshore fishing around Charlotte Harbor and the Ten Thousand Islands. The casting deck, rod holders and elevated second station all support that shallow-water-to-nearshore use.
All three 266 Cayman SD listings on US Marine Connection are in Fort Myers, Florida, and all three include photos. There are no other cities represented for this model at the moment. If you are shopping from outside Southwest Florida, the listings themselves are your starting point, and you would be arranging to see the boat in Fort Myers.
By the numbers on the site, the 246 Cayman has 6 listings from 2026 to 2027 asking $115,949 to $139,078, median $132,690, so it sits well below the 266 Cayman SD's $189,938 to $205,697 range. The R257 shows 5 listings, 2025 to 2027, at $157,185 to $188,868, median $186,963, closer but still under. Beyond price, years and listing counts, the site does not give comparison specs.
Answers are written from approved, priced listings on US Marine Connection— asking prices, not sale prices — and from what the dealers' own descriptions say. Figures in the strip above are live; the answers refresh as inventory changes.
Robalo 266 Cayman SD listed now
DealerFort Myers, FL
Center console · Excellent condition
Fish Tale Boats
Nationwide Delivery Available
$189,938
View details
DealerFort Myers, FL
Center console · Excellent condition
Fish Tale Boats
Nationwide Delivery Available
$192,003
View details
DealerFort Myers, FL
Center console · Excellent condition
Fish Tale Boats
Nationwide Delivery Available
$205,697
View details