The Journal · Routes

A sunset route through Star Island.

2026-05-07 · 7 min read

The sunset route is our most-run charter. Two-thirds of the bookings on our calendar over the last twelve months. Most guests, when they enquire, name the occasion — anniversary, proposal, milestone — and ask which charter we recommend. The honest answer, almost always, is the same: a four-hour sunset, the route we have written here.

The departure

We sail from Miami Beach Marina, slip eighteen, three hours before sundown. In June that means a 4:50 PM departure. In December, 2:30. Our captain has been on board for an hour by the time the guests arrive — fueling, briefing the deckhand, walking the boat once with a clipboard, placing the welcome arrangement on the salon table.

The first ten minutes of any charter are about settling. The boat is moving slowly. The deckhand offers champagne. The guests find their place — flybridge for the people who want to talk, salon for the people who want to read, swim platform for the children. The captain checks in once, briefly, then returns to the helm.

The southern leg, past the islands

Out of the marina we run south down the western edge of the bay. Star Island is on the right. The estates begin around mid-island — the famous houses, the famous owners, the famous walls. Most guests want to slow down and look. We drop to seven knots. The captain narrates briefly, by request, or stays quiet. It depends on the guests.

Past Star Island we cross to Hibiscus and Palm. The water is shallower here — the captain knows the channels by feel — and the light begins to go gold. By this point, on a typical evening, the guests have stopped looking at their phones.

The anchor at Stiltsville

Stiltsville is a cluster of seven wooden houses on stilts in three feet of water at the southern end of the bay. They are the last of what used to be a community of forty in the 1960s. The houses are now part of Biscayne National Park. We anchor on the deep side of the line — about eight feet of water — and the deckhand opens the swim platform.

This is the middle of the charter. About forty-five minutes in the same place. People swim. Champagne is opened. The light is at its best from about thirty minutes before sundown until ten minutes after. On a clear evening the houses sit black against an orange sky and the bay is a sheet of copper. It is, photographically, the strongest hour we have on the bay.

The proposal moment

If the charter is a proposal, this is when it happens. We have run forty proposals at this anchor in the last two years. The script, after some refinement, runs roughly: the captain anchors, the deckhand pours, the music shifts to something quieter, the guest of honor is asked to look at the houses by their partner. The ring is in the partner's pocket. The light is gold.

It works because it is simple. The charter has nothing extra in it. The light does the work. The captain and crew, having been briefed, are ten feet away pretending to be busy. Forty proposals; forty yeses.

The skyline on the way home

We weigh anchor about thirty minutes after sunset. The captain runs the eastern edge of the bay on the way back. The Miami skyline is on the left. By the time we are halfway home, full dark has fallen and the skyline is lit. From the bay, in clear air, downtown Miami is one of the most visually striking skylines in the United States. Most guests, having seen it from cars and beaches, see it from the water for the first time on this leg.

The yacht arrives at the dock about an hour after sundown. The deckhand has packed the welcome arrangement. The captain hands the guests off to a waiting Uber. The whole thing — from the ten-minute settle to the dock — has taken four hours and felt, to most guests, like an evening rather than a charter.

What we look for in the light

Not every evening is right for this route. Cloud cover can flatten the light. A strong south wind can make the Stiltsville anchor unsuitable. The captain checks the radar an hour before departure and has the right to suggest a route change. Most evenings the route holds. About one in eight, we move the anchor north to a calmer spot.

The light, when it is right, is the reason this is the charter we recommend. The route is, in effect, a vessel for the light. Everything else — the boat, the music, the champagne, the timing — is engineered around it.