A sunset sail down the Hudson on the Sloop Clearwater — a 106-foot, 1969 wooden replica of the 18th-century cargo sloops that worked the river before the steam age. The bride takes a turn at the tiller while the mainsail snaps over Constitution Marsh and Bear Mountain rises ahead. The boat docks back at Beacon by 9pm. Stay at The Roundhouse — a converted 19th-century factory at the foot of Beacon's main street. Saturday morning at Dia:Beacon's 240,000-square-foot light-and-space gallery (Richard Serra, James Turrell, Agnes Martin), lunch at Roundhouse, an afternoon walk along the Hudson Highlands ridge to Breakneck. Decompression on Sunday at Magazzino Italian Art in Cold Spring.
Five quick questions, then we build the full itinerary — lodging, daily schedule, dining, bars, the group-chat message — and drop you into a Trip Room you can share with the bridesmaids.