Wing foiling is the newest discipline in water sports: a handheld inflatable wing (like a kitesurfing kite but flatter, held in your hands) paired with a hydrofoil board. It's minimal, portable, and astonishingly fast. For a Manhattan circumnavigation, it's also an exercise in frustration.
The wing foiler's primary constraint is wind stability. You need steady 12+ knots to get airborne and stay on the foil. Light and variable wind becomes slogging. Manhattan's wind environment is unreliable due to building shadows, thermal circulation, and river canyon effects. The Hudson River can have 20+ knots, while the East River gets chopped and shadowed. The Harlem River is especially sketchy—narrow, surrounded by buildings, wind funnels and swirls.
Wind shadows from Manhattan's skyline are a permanent hazard. The tall buildings create massive dead zones on the lee side of the island. You're foiling in one moment and completely becalmed in the next. When you lose wind, you drop off the foil and slog through water like a conventional board until you reach better wind again.
The Harlem River is the most problematic segment. It's narrow (only a few hundred feet wide in places), completely surrounded by buildings, and the wind is turbulent and variable. Thermals rising from the streets create unstable wind patterns. Wind direction can change 30+ degrees in a short distance. You may drop off foil multiple times.
No mast height issue. You're holding the wing in your hands. Bridge clearances are irrelevant. But the geometry of narrow passages and building proximity means wind is harder to predict and maintain.
The real enemy is inconsistency. Full Loop wind, especially around Manhattan, rarely stays steady and strong for the entire circumnavigation. You'll drop foil and have to paddle or kick the board. A sustained 45-minute foiling run might be interrupted by a 20-minute slog through dead wind zones.