The Upstart 16 is a high-performance, one-design racing dinghy designed by the legendary British naval architect Ian Proctor and manufactured primarily by O'Day in the United States during the late 1960s and early 1970s. Introduced as a response to the growing demand for fast, planing centerboarders, the Upstart 16 was engineered to bridge the gap between stable family daysailers and elite international racing classes like the 505. Measuring exactly 16 feet with a generous 6-foot 4-inch beam, the boat features a lightweight fiberglass hull designed for rapid acceleration and responsive handling. While it shares a design pedigree with other Proctor-designed vessels such as the Wayfarer and the Topper, the Upstart 16 was specifically marketed as a "performance machine" for sailors who prioritized speed and technical agility over leisure.
Upstart 16 Information, Review, Specs

- Make
- Upstart
- Model
- 16
- Builder
- Starcraft Corp.
- Designer
- J. R. Macalpine-Downie / Dick Gibbs
- Number Built
- Production Year(s)
- 1967 - ??
Sailing Performance & Handling
The Upstart 16 is defined by its planing hull and high power-to-weight ratio. With a total sail area of approximately 160 square feet—comprised of a 110-square-foot mainsail and a 50-square-foot jib—the boat carries significant canvas for its 450-pound displacement. This configuration, combined with its relatively flat aft sections, allows the boat to break onto a plane in moderate breezes, a characteristic often highlighted in original O'Day marketing materials as a primary selling point.
Handling is characterized by high sensitivity; the boat utilizes a trapeze for the crew to manage the considerable heel generated by its tall rig. According to historical technical reviews, the Upstart 16 tracks exceptionally well upwind due to its deep, pivoting centerboard, which extends to nearly 5 feet when fully deployed. However, the boat's responsiveness requires an experienced hand, as the Proctor-designed hull is prone to "tripping" over its own bow if the weight distribution is not managed carefully during high-speed reaches. Unlike its sturdier sibling, the O'Day Day Sailer, the Upstart 16 feels more like a pure racer, offering immediate feedback to every adjustment of the sheets or tiller.
Known Issues & Buyer’s Checklist
Prospective owners of an Upstart 16 must account for the age of the fiberglass and the specific stresses associated with high-performance dinghy racing. A primary area of concern is the mast step and the surrounding deck structure; because the boat was intended for aggressive sailing, the downward compression of the mast can lead to stress cracking or deck sagging in older models. Buyers should also inspect the centerboard trunk for leaks or delamination, as this is a high-stress point that is difficult to repair once the fiberglass integrity is compromised.
The hull-to-deck joint is another critical inspection point. In many O'Day models from the early 1970s, this joint was fastened with a combination of adhesive and mechanical fasteners that may have weakened over decades of thermal expansion and rig tension. Furthermore, because the Upstart 16 utilizes a trapeze, the chainplates and their internal backing plates should be checked for signs of "crevice corrosion" or movement. Finally, given that the class is no longer in active production, original hardware—specifically the unique rudder gudgeons and centerboard tackle—can be difficult to replace, often requiring custom fabrication.
Community & Resources
Support for the Upstart 16 is largely integrated into the broader community of O'Day enthusiasts. Technical data and historical brochures are frequently preserved by the O'Day Owners Association, which serves as the primary repository for rigging diagrams and restoration advice for these vintage performance boats. While the boat does not currently maintain a formal one-design racing circuit, it remains a favorite among "classic plastic" collectors and dinghy sailors who appreciate the Ian Proctor design philosophy.
The Verdict
The Upstart 16 is a relic of the "performance revolution" of the 1960s, offering a visceral sailing experience that belies its age. It is a boat for the technical sailor who enjoys the physical challenge of trapeze work and the thrill of a planing hull.
Pros:
- Exceptional Speed: One of the fastest boats in its size class from the era, capable of consistent planing.
- Designer Pedigree: Benefits from Ian Proctor’s expertise in hull efficiency and rig balance.
- Technical Engagement: Provides an excellent platform for learning advanced sail trim and trapeze techniques.
Cons:
- Stability: High-strung and "twitchy," making it unsuitable for beginners or casual family outings.
- Aging Hardware: Finding original replacement parts for the 1970s-era fittings is increasingly challenging.
- Structural Risks: Vulnerable to deck compression and centerboard trunk issues if not properly maintained.
Measurements
Construction & Hull
- Construction Material
- Fiberglass
- Hull Type
- Monohull Sailboat
- Keel Type
- Centerboard
- Rudder
- 1x —
- Ballast
- -
- Displacement
- 550 lbs
- Water Capacity
- -
- Fuel Capacity
- -
Dimensions
- Length Overall (LOA)
- 16.5 ft
- Waterline Length (LWL)
- 15.42 ft
- Beam
- 6.25 ft
- Draft
- 3 ft
- Max Headroom
- -
- Air Draft
- -
Rig & Sails
- Rig Type
- Fractional Sloop
- P (Main Luff)
- -
- E (Main Foot)
- -
- I (Foretriangle Height)
- -
- J (Foretriangle Base)
- -
- Forestay Length (est)
- -
- Sail Area
- 218 sqft
Calculations
- Sail Area / Displacement (SA/D) Ratio
- 51.96
- Ballast / Displacement Ratio
- —
- Displacement / Length Ratio (D/L) Ratio
- 66.97
- Comfort Ratio
- 4.7
- Capsize Screening Formula
- 3.05
- Hull Speed
- 5.26 kn