A road trip down the Atlantic Coast will take you past the historic towns of Plymouth, Massachusetts and Newport, Rhode Island, through the hustle and bustle of New York City, along Maryland's Chesapeake Bay coast to Virginia Beach and North Carolina's Outer Banks. From there, you'll pass through the gorgeous, sleepy hamlet of Savannah, Georgia and down to the oldest city in the U.S., St. Augustine, Florida. Then it's an oceanside cruise along the Space Coast to vibrant Miami Beach and finally, colorful Key West. Sure, you could take I-95 all the way from Boston to Miami, but with several detours and scenic byways this trip is more than 2,400 miles full of beaches, woodlands, two-lane country roads, vintage diners, charming small towns, and urban adventures.
You'll want to plan at least half a day to accomplish the 2.5-mile Revolutionary Freedom Trail in Boston, Massachusetts. Afterwards, the best place to grab a bite to eat is historic Faneuil Hall, which features dozens of food stands. If you have time (or you're traveling with kids) visit the New England Aquarium and the Museum of Science.
The entire East Coast is dotted with beautiful lighthouses, and one of the best is the Montauk Lighthouse Museum in East Hampton.
Once you reach Maryland, visit the 41,000-acre Assateague Island National Seashore, a refuge for wild ponies.
A short drive south of D.C. is the historic Fredericksburg and Spotsylvania National Military Park, site of one of the bloodiest battles of the Civil War.
The Inn at Rodanthe, made famous in the movie Nights in Rodanthe, almost fell into the ocean—it's since been moved to a safer location off the beach, but still makes for an impressive photo op.