Long Wharf once reached half a mile into the harbor, far enough that ships tied up at its head and unloaded rum directly onto the granite. Built in 1710 and extended repeatedly through the eighteenth century, it was the longest wharf in colonial America. Landfill has since swallowed most of it. The stub that remains, at 1 Long Wharf, is where the modern boston harbor sunset booze cruise begins. The drinking is not incidental to this water. Boston's harbor economy ran on molasses shipped from the Caribbean and distilled into rum along the North End shoreline; by the 1740s the town supported more than thirty distilleries. Merchants who financed those voyages built the Custom House Tower, whose clock face still marks the skyline visible from every departing deck. The harbor that carried the trade later carried the tea overboard in December 1773, a few hundred yards south of where the gangways drop today. What the fleet crosses now is an inner harbor cleaned by one of the largest public works projects in American environmental history. The Boston Harbor Project, completed at Deer Island in 2000, ended the discharge of raw sewage that had made these waters a national embarrassment. Harbor seals returned. So did striped bass, and with them the recreational fleet. Boston sunset cruise tours are a direct consequence of that cleanup, not a coincidence of it. The vessels differ in character rather than route. A classic tall ship works under canvas, her rig a survival of the schooner tradition that once crowded these piers. Motor yachts trade sail for stability and wide open decks. Narrated skyline sailings run past the Rowes Wharf arch, the Charlestown Navy Yard where USS Constitution has been moored since 1897, and the Boston Light on Little Brewster Island — first lit in 1716, the oldest continuously used light station site in the United States. Champagne sailings depart from Rowes Wharf itself, beneath the 80-foot rotunda arch completed in 1987. The geography does the rest. Boston Harbor opens east-northeast, which means the sun sets behind the city rather than over open water — the skyline goes to silhouette while the Financial District glass burns orange, a reversal of the usual coastal sunset. The Zakim bridge cables catch the last light. Logan's approach path runs low overhead. That inverted angle is the argument for the boston harbor sunset booze cruise as a form: the drink is the occasion, but the view is the reason the occasion holds. Standard adult tickets for a 90-minute sunset sailing run 31.5 USD. Boston harbor sunset booze cruise tickets cover the deck, the crossing, and the light. The bar is separate, as it has been on this waterfront for three centuries.