It did not seem to perturb the Bermudians, with each appearance greeted by the same level of enthusiasm.
For the locals it is about embracing what makes their little island special.
The six America's Cup teams have also embraced this place. While Emirates Team New Zealand have called Bermuda home for the past five weeks, others, like Oracle and Artemis have been based on the tiny crescent-shaped island in the middle of the Atlantic for over two years.
The giant wingsails of the America's Cup Class catamarans have been a permanent fixture on the water of the Great Sound in the lead-up to the regatta, which, weather permitting, gets underway on Saturday.
On shore the sailors are just as visible, with virtually every second scooter being driven by someone in team garb. They spend their days hurtling around on the water in high-powered marine rocket ships, capable of reaching speeds of up to 90km/h. They return home of 125cc scooters, barely capable of reaching the 40km/h speed limit.
Scooters are the mode of transportation of choice for locals and tourists alike. With just one main road winding its way along the length of the island, traffic congestion is a major issue.
It's just one of the many logistical problems facing organisers of this year's event. For an island the size of Waiheke, the influx of thousands of team personnel, family and friends, event staff and sailing fans has put pressure on everything from wifi networks to water systems.
With turquoise waters and pink sand beaches, it is a beautiful place to hold a yacht race. But the logistics are ugly.