The secret to navigating this playground of preppies and presidents – and the circuit of islands they invade each summer – is to steer clear of the traffic snarls and go entirely by ferry. Grab a bike, a backpack, a bathing suit, find the Amtrak, and go.
New London, CT (Arrive on Amtrak)
Kill time at the dockside art galleries and Captain Scott's Lobster Dock. The no-frills picnic tables overlooking busy docks where your meal just came in are part of the charm.
Block Island, RI (Block Island Express)
Cheaper and funkier than its neighbors, Block Island's most dramatic sight is the 200-foot-high Mohegan Bluffs. The best way to see the island is to hike its 30 miles of Greenway Trails. Stay at the creaky old Surf Hotel. Room 13 is the corner room with a view of the harbor.
Newport (B.I. Ferry)
Disembarking at the ferry slip is like the summer-arrival scene in 'Jaws' – a clamoring, lawnchair-toting mass of humanity. Saddle up and flee to the Cliff Walk that runs past marble mansions; surf the breaks at First Beach; bike the island's coast along Ocean Drive; grab a sunset Cuba Libre in the attic-like, third-floor bar at Fluke, above Bowen's Wharf.
Martha's Vineyard (One-hour RIPTA bus ride to Kingstown, RI, then bike 16 miles to the Vineyard Ferry in Quonset)
Blow past the SUV traffic and pedal down island, to Gay Head Public Beach, a cliff-backed stretch, great for walking and tanning. Stay at the Duck Inn, a 200-year-old former farmhouse. The best surfing is at the Atlantic-facing beaches, including the residents-only Squibnocket. So, rent a kayak, paddle to Stonewall Pond, ditch it, and walk to the beach.
Nantucket (Hy-Line Cruises)
For wild, knots-in-your-hair beachcombing, there are 4x4 rentals to explore the far west-end forks. Skip the upscale Galley Beach bar, and its pomegranate-sipping arrivistes, for the locals selling fruits at the two-block-long Nantucket Farmers & Artisans market.
Returning: Hy-Line Cruises to Hyannis, Massachusetts. Then take the Amtrak.
Costs: From Hartford, ride an Amtrak to New London for $21. Getting to Block Island is $25 on the express, and then another $12 to get to Newport via ferry. A six-dollar bus pass will take you to Kingstown. Hop islands from Nantucket to Hyannis for $40.