How to plan a proposal on the water

Timing the sunset, where to hide the ring and what the crew does while you ask.

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We help with about thirty proposals a season. Most of them go perfectly, and the ones that wobble always wobble for the same three reasons: the light, the ring or the crew.

This is what our skippers have learned from all those evenings, so that the only surprise on the boat is the one you planned.

Timing the sunset

Book the sunset charter, not the sunset itself. We leave Pier 6 about ninety minutes before the sun goes down, which gives you time to settle, a glass of something, and the best light on the water as we come out past the lighthouse.

The moment most people choose is about twenty minutes before sunset, when the light turns gold and the wind usually drops. Your skipper will tell you quietly when it is coming.

Twenty minutes before sunset, past Thomas Point, the moment most people choose.

Choosing the boat

For two people we recommend Petrel or Halyard 26 with a club skipper. A sailboat heeling gently in a warm breeze does a lot of the work for you, and there is room to stand at the bow without anyone else in the photo.

“The skipper is the only other person on the boat who knows. That is the way it should be.”

If the weather turns, we move the charter to another evening at no charge. Several couples have told us the second evening was better than the one they planned.

Where to hide the ring

Do not keep the ring in a pocket you will reach into on deck. Give it to the skipper at the dock, in its box, and agree on a signal. It goes in the chart table drawer and comes out exactly when you need it, which is also the only place on the boat it cannot fall overboard.

What the crew does

Our skippers have done this many times. When you give the signal they hand over the box, take the helm, look firmly at the horizon and keep the boat steady. If you want photographs, they will take them from the cockpit and then disappear behind the mast.

Before you book

Call the dock office and ask for the proposal notes. We keep them short, and we keep them secret.

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