Overview The Around Long Island Regatta is a distance sailing race that starts off the Statue of Liberty in New York Harbor, heads out into the open Atlantic, rounds Montauk and comes back down Long Island Sound to finish at Sea Cliff, 207 miles on the rhumb line. Since 2025 there is a second course, the 250-mile Around the Islands, which adds Block Island; the organizers call it the longest distance race of any regatta between Annapolis and Newport. Sea Cliff Yacht Club founded the race in 1977 and runs it, and the 2026 race was the 49th. On site The captains' meeting is held on the Jersey City side of the harbor, at Liberty House in 2026. In 2025 the starts went off every ten minutes from 11:05 in the morning. Spectators watch from the Manhattan Yacht Club's Willy Wall, a floating bar anchored off Ellis Island with a cash bar, reached by a launch from Liberty Landing Marina every half hour. From 2025 every boat carries a YB tracker, so the race can be followed online for the days it takes, and in 2026 the race closed with an awards and beach party at Sea Cliff Yacht Club on the Sunday afternoon. Audience The entry list runs from weekend cruisers and college sailors to offshore racers, on boats of 24 feet and up. In 2025 a U.S. Navy midshipmen crew on Wahoo was first to finish the Around Long Island course, the Storm Trysail Club entered four boats, and a Bohemia Trophy went to the best first-time entrant. Track record In 2025 Halve Maen won the John B. Thomson Trophy on the new Around the Islands course, Max took the Around Long Island Regatta Trophy, Daffodil was the first multihull home and Habiru won the Youth Challenge Cup. That year also added an award for the best photo shot on board. Brand presence The tracker is a sponsor position: the race-tracking level ties a brand to the live tracker that follows every boat around the course. Above it sits the title role, and below it tiered levels named for ranks from Commodore down to Midshipman, plus a Rock the Dock sponsorship and a dealership level. In 2025 Wölffer Estate Vineyard was official rosé, with New England Yacht Rigging and PhotoBoat.com as official suppliers.