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Triple Tail represents the pinnacle of Winter Custom Yachts’ craftsmanship, combining luxury, functionality, and versatility into a 66-foot convertible tailored for family adventures on the water. Designed with a focus on fishing, long stays at sea, and supporting water sports, Triple Tail brings together all the right features to meet the owners’ needs in a spacious and quick platform.
Cockpit/Mezzanine
I met Tim Winters at his shop in Hubert, North Carolina, to sea trial and get a thorough walk through of his latest creation.
The cockpit is an ideal spot for both serious anglers and family members, with traditional features such as a transom fishbox and a centerpiece Release Trillion fighting chair with rocket launcher back. Forward of the transom is a cavernous lazarette with pull out storage drawers to port and starboard as well as a center storage compartment to house cleaning supplies and watersports gear. In addition, steering components are within easy reach along with the SeaFlo dry bilge system.

The mezzanine provides a comfortable sofa with AC vents along the back rest, perfect for watching baits on a hot summer day. Also, there are multiple areas featuring ice dumps, chillers, and storage. Each armrest for the sofa and starboard seat has integral drawers for various gear. The starboard seat hides a grill in a pull drawer underneath. Under each gunwale, two L-shaped doors conceal the washdowns, cablemaster controls, and storage for brushes and chamois.
The design and layout of the entire cockpit allows all members of the family to enjoy the activity of their choice.
Flybridge
The flybridge is built for entertaining and functionality, with the port side peninsula helm the focal point. Aft of the helm are three Release helm chairs while forward sports a 3-person chaise lounge. A sofa along the starboard bridge wing provides additional seating with a flip/flop Release ladder back, allowing you to face fore or aft. A cabinet forward of the sofa conceals a refrigerator while a chilled freezer under the chaise lounge provides gracious food storage for long trips.

The helm is functional and simple, housing three Garmin 22-inch screens with push button switches below the two outer screens and bilge light indicators under the center screen.
The teak helm pod and Release wheel are centerline with a glove box to port which houses the VHF microphones, Omni sonar keypad, and transmission controls. Overhead are the MTU screens, a pair of ICOM VHF’s, and the Garmin Autopilot display. Miya Epoch Teaser reels are easily accessed overhead in a second compartment. Winter’s thoughtful design has everything within arm’s reach for maximum enjoyment and fishability.
Above the bridge, Triple Tail soars towards the sky with a Custom Palm Beach Towers tuna tower providing elevated views for a spotter.

Interior Accommodations
Entering the salon, you feel wrapped in warmth by the horizontal grain walnut veneers. Just inside the salon door are controls that change the windows from slightly tinted to white, transforming the entire salon into a private oasis. A credenza to starboard houses glass and bottle storage, an electrical panel, and an ice maker. A fifty-five-inch TV rises from the credenza top facing the L-shaped sofa. Moving forward, a dinette that seats six provides abundant storage under the seats and the raised floor. The galley, indeed built for a cook, features dual refrigerator/freezer drawers, a Wolf speed oven/microwave, and a Wolf cooktop, as well as customized storage for dinnerware, utensils, and cookware. The aft countertop pulls double duty with two barstools to keep the entire family close, making the salon the perfect choice for family time or meetings before traveling to the fishing grounds. The brow is utilized for cabinet space above the galley counters and above the dinette. You can access inside the brow for additional storage and Winter provides a pullout pantry storage drawer just forward of the dinette.

Down below, an over-under bunk room is to starboard. Reel storage is available under the bottom bunk. Moving forward, the washer dryer is enclosed behind a flush door next to another bunk stateroom. The guest room all the way forward accommodates a double berth with a raised single bunk to starboard. As expected, abundant storage is found throughout each stateroom. Walking aft on the port side, you’ll find rod storage behind a flush panel door. The master hosts a queen berth with storage below and behind the headboard. The closet space in the master is massive with multiple cedar lined lockers and drawer storage. The master ensuite head features a beautiful stone-tiled shower floor and beautiful multi-toned countertops.
Winter’s use of space in Triple Tail is fantastic, providing four spacious staterooms and three full heads in a sixty-six-foot platform.

Engine Room
Accessing the engine room through the centerline hatch in the mezzanine is effortless. As you descend, the Seakeeper 18 is aft and easily accessed for service. To accommodate the family’s water sports, there are storage racks on each side for several Seabobs. The engine room is meticulously arranged for redundancy and ease of maintenance. Seawater pumps and strainers are housed in two dedicated compartments. The ElectroSea control, Omni transducer, and Fireboy system are located forward and on center. Batteries sit outbound in customized ventilated boxes, while a pair of Kohler generators are housed behind each engine on the aft bulkhead. Winter also climate controlled the engine room, ensuring general maintenance and inspections are far more comfortable to complete.
Performance
Since Triple Tail was scheduled to leave the next morning for the Palm Beach Boat Show, our sea trial had to be relatively limited. As we left the basin, Winters pushed the throttles up to an effortless cruise of 31 knots at 1800 RPM burning 125gph. The hull simply lifted out of the water without any bow rise, providing great visibility from the helm. If you are in a hurry, a 2000RPM high cruise provides 37 knots at 150gph, while wide open throttle at 2450RPM delivers an impressive 42.5 knots.
Triple Tail stands out as a multi-purpose sportfish yacht that blends fishing capability, luxury, and practicality. Whether it’s fishing, cruising, or enjoying watersports, this custom-built yacht is a dream for any family looking to make the most of their time on the water. Designed to thrive in the waters of Puerto Rico, it’s ready for both adventure and relaxation.
Specs & Notable Features
- LOA: 65’10”
- Beam: 18’7”
- Draft: 5’6”
- Displ.: 103,000
- Fuel: 1,800 gal.
- Water: 360 gal.
- Power: MTU 12V2000M96X 2000hp
- Gears/Ratio:Twin Disc MGX-6599a 2:1
- Propellers: CJR
- Climate Control: Dometic
- Notable Features:
- 4 Stateroom 3 full head layout
- Large Chaise lounge and voluminous seating on the bridge
- True SUV on the water built for all activities.