San Francisco Waterfront: Enjoy the more spectacular view of S.F.—offshore, that is—and you begin to notice what the onshore tourists are snapping pics of: That’d be you, and your full-sailed catamaran, slipping past the piers. Start at Crissy Field, working your way east. When you get close to the Ferry Building on the eastern shore, tie up at the new public dock at Pier 11/2 and walk up for a cocktail at La Mar.
Ayala Cove at Angel Island: As close to a Caribbean sailing experience as you’ll find in the northern latitudes: Calm winds, a sandy beach, picnic benches and BBQs, and public docks and mooring balls for sailors, who can hike up to the top of the island for a three-bridge, 360° panorama of the bay.
Golden Gate Bridge to Sausalito: If sailing under the Golden Gate is on your float plan, most captains will take you out there in the morning before the afternoon winds turn a pleasure sail into a whitewater adventure. On the way back, cruise into Sausalito and Richardson Bay, and tie up for lunch at Horizons’ own dock.
Oakland/Alameda Estuary: For sailors venturing to the East Bay, there is a there there, despite what Gertrude Stein said. Sailing into the estuary from Treasure Island, float downwind (carefully) past giant container ships on the first leg of this daysail. Then turn into the estuary’s main channel with dozens of friendly marinas, starting with Jack London Square.