The remote lighthouse at the end of a sandy beach is just as much a symbol of New England as Paul Revere on his horse. After the long winter, southern New England positively explodes with beach bums and boaters, who flock to the Atlantic for fun in the sun. Pristine beaches, maritime history, and plenty of greasy seafood await…
Starting out in Boston , get up close and personal with sealife at the New England Aquarium , one of the best in the world. At night, take a harbor cruise to see the city skyline the way it was meant to be seen—from the water.
Book ahead to take your car on the fast ferry across Massachusetts Bay to the funky town of Provincetown  (1.5 hours), known locally as P-Town, for breathtaking views, art galleries, and eclectic shops. When you tire of shopping, relax at Race Point Beach . (If you forget to book ahead for the ferry, you can drive to P-Town along I-95, I-495, and Route 6; 3 hours.)
On your second day in P-Town, take a whale-watch  or deep sea–fishing charter  onto the rough waves of the Atlantic. In the afternoon, tour the remote dune shacks where artists and writers have found inspiration among the shifting sands.
Drive down Route 6 along the scenic Cape Cod Seashore to Hyannis  (1.5 hours), the heart of the Cape and summer retreat of the Kennedys.
In the morning, leave the car on shore and take a ferry across to one of two island destinations, the proper and quaint Nantucket  (2 hours) or the downbeat and trendy Martha’s Vineyard  (1 hour). Spend your first day in town exploring the quaint downtowns of Nantucket Town or Oak Bluffs . On day two, rent a bicycle and take a ride out to ‘Sconset or Gay Head for a picnic on the beach. In the afternoon, visit the Nantucket Whaling Museum  or go celebrity-hunting on the streets of Edgartown .
After taking the ferry back to land, drive down the coast, along Route 6, I-95, and Route 114, to the yachting capital of Newport  (1 hour). Take a walk along the dramatic Cliff Walk , and tour one of the impressive mansions.
It’s time to hit the beach, with an all-day excursion across the East Bay  to the quiet sands of Sakonnet Point  (1 hour), perhaps taking time out for a free sample at Sakonnet Vineyards . After you’ve had your fill of the beach, drive back to Newport for the night.
Head down I-95 along the Rhode Island  coast and cross into Connecticut  to base yourself at the charming fishing village of Stonington  (1 hour). Then take the rest of the day to raise the rigging at the reconstructed 19th-century maritime village of Old Mystic Seaport , a hands-on museum of maritime history. Be sure to grab a slice at Mystic Pizza  before returning to Stonington for the night.
One more day to get out onto the water. Drive up I-95 to the little village of Stony Creek (1 hour), where you can rent a kayak for a tour of the Thimble Islands  and come face-to-face with shorebirds and maybe even a dolphin. Spend the night in Stony Creek. The next day, take I-95 back up to Boston  with a boatload of happy memories (2.5 hours).