A road trip down the Atlantic Coast will take you from very early historic towns, like Plymouth in Massachusetts and Newport in Rhode Island, through the hustle and bustle of New York City, down Maryland's Chesapeake Bay 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 America's oldest city, St. Augustine Florida. Then it's an oceanside cruise along the Space Coast to vibrant Miami Beach, and you can finish off your trip in colorful Key West. It could be the trip of a lifetime, if you know where to find the can't-miss spots along the route. Sure, you could take I-95 all the way from Boston to Miami, but there are loads of detours and scenic byways that will take you on and off the highway. From Boston to Key West, you're looking at 2,400 miles of beaches, woodlands, two-lane country roads, vintage diners, charming small towns and urban adventures.
Beginning in Massachusetts, walk through history along the Revolutionary Freedom Trail in Boston. You'll want to plan at least half a day to accomplish the trail. It's 2 and a half miles long and takes about 2-3 hours to walk. Plus, you're definitely going to want to stop at a lot of the historic sites. While in Boston, there's also loads of great places to grab a bite to eat, but the best place is historic Faneuil Hall, where dozens of local merchants have food stands, so you can take your pick of the best that Boston has to offer. If you have time, and you're traveling with kids, the New England Aquarium and the Science Museum are two must-visits in the city.
From Boston, head south to historic Plymouth and experience the harsh reality of 17th century life at Plimoth Plantation. It's a great way to learn about the life and times of America's earliest European settlers. The plantation is "a living history museum," showcasing the original 1627 English settlement. All the colonists you see walking around are actors who will answer your questions authentically in character.
As you leave Massachusetts, take a detour to Fall River and see Battleship Cove, which features the world's largest collection of WWII naval vessels.
When you're hungry, head over to White Horse Tavern in Newport, Rhode Island. They serve up delicious regional, upscale cuisine in a historic tavern that dates back to 1673.
2000 Montauk Highway (On The Point By Montauk Liighthouse), Montauk, NY, US
The entire East Coast is dotted with beautiful lighthouses, and one of the best is the Montauk Lighthouse Museum in East Hampton. There's also the nearby beach town of Cape May in New Jersey, which is home to another stunning historic lighthouse, the Cape May Lighthouse, built in 1859. But, the charming seaside hamlet of Cape May alone is worth a detour.
Once you reach New Haven in Connecticut, definitely visit the New Haven Lighthouse. Not only is this a gorgeous historic lighthouse from the mid-1800s, it also features a beautiful, antique Carousel that was built in 1916.
When you reach New York City, see a different side of the city with a mile and a half walk along The High Line. What makes the High Line so cool is that it's an elevated walking park that was built atop an unused section of the New York Central Railroad!
For some great pizza there's Lombardi's, which has been serving up scrumptious thin-crust pizza since 1905.
Best Time to Travel the Atlantic Coast: During winter the road conditions can vary, but in the Northern part of your trip be prepared for weather delays from December through mid-March. Spring is off-season, so you should be able to score some good rates at hotels along the route. Summer is high tourist season all up and down the Atlantic coast, which means hotel rates will be high and crowds at stops along your route will also be a factor. Fall however, is an ideal time to travel up and down the coast. Not only is the fall foliage particularly gorgeous from end of September through early November in New England, but once you get down to Georgia and Florida the temperature up north will be chilly, so you'll welcome the warmth of the south.