Great spot located right at the entrance to the Inner Harbor. It's not really an island; take Day Boulevard out to this green spot, dominated by Fort Independence. The Harborwalk encircles the island, and there's lots of lawn to spread out a blanket and chairs. Parking for about 250+ cars; more parking back on Day Boulevard.
You can drive from the mainland to Deer Island Park on Tafts Avenue; it should provide a good viewing spot, but bring binoculars. And don't be put off by the wastewater treatment plant next door.
Summer Street Bridge, South Boston
Five Navy ships will pull into the Black Falcon Cruise Terminal to dock: The USS Gravely, a guided missile destroyer; the FGS Hessen, a German air-defense frigate; the HMCS Preserver, a Canadian auxiliary oiler replenishment ship; the HMCS Iroquois, a Canadian destroyer, and the RFA Argus, a British primary casualty receiving ship. You'll have to park somewhere on Summer Street and walk out onto the bridge. Assuming the police let you lollygag there, you'll have a good view of the ships.
Seaport Boulevard/Northern Avenue
Two piers along here will host ships:
>The USS Wasp, an amphibious assault carrier, is the biggest ship to arrive and will dock at Massport's Marine Terminal/North Jetty, which is on Kennedy Avenue off Northern Ave.
>Two piers north of that, the Fish Pier will feature four of the five Tall Ships that are coming as part of OpSail: the Cisne Branco from Brazil, the Guayas from Ecuador, the Gloria from Colombia, and the Dewaruci from Indonesia.