6 East Coast USA road trips

Home to golden beaches, vast wetlands and grand cityscapes, the Eastern USA offers a trove of memorable travel experiences. 

The challenge is deciding where to go - no easy task in a region with thousands of attractions scattered across dozens of states. That’s where we come in. Start your planning with one of these six itineraries. Each showcases a different facet of the American experience, from the allure of the South to the island-studded coastlines of New England. 

We’ve kept our suggestions to trips of five to 10 days, though you could easily extend your journey or combine a few (or all!) of these itineraries into one epic road trip traveling the length of the Eastern Seaboard. 

1. Drive across the sea in South Florida 

5-day itinerary
Distance: 175 miles (282km)

On this five-day trip, get a taste of Florida’s most dynamic city, soaking up Miami’s Art Deco architecture, lovely beaches and street art. Afterwards, rent a car and hit the road, traveling the full length of the Overseas Highway, which stretches for 113 miles over 42 bridges linking some 44 different islands. The journey ends in the colorful city of Key West. 

Miami: 1 day  

Head straight to the shore for an early-morning stroll (sunrise is magical) along the golden sands of South Beach. Afterwards, enjoy the eye-catching architecture on a wander through the Art Deco Historic District, and shop and snack along palm-lined Lincoln Road Mall. In the evening, head to Wynwood to check out cutting-edge street art at Wynwood Walls, and grab a bite at the nearby Taco Stand - or at the speakeasy-style Hiden, a Michelin-starred Japanese restaurant concealed within.

Next stop: Get behind the wheel for the 70-mile drive down to Key Largo. 

Detour: Make a side trip to the Everglades for guided wildlife encounters and other adventures in the national park (add one additional day).

Key Largo: 1 day  

Take the slower, but more scenic Card Sound Bridge (stopping for a bite perhaps at Alabama Jack’s) to reach Key Largo, the best-known of the Upper Keys. Go for a snorkeling or diving excursion, followed by a mangrove stroll at John Pennekamp Coral Reef State Park, then enjoy sunset views from a well-placed restaurant-bar facing Florida Bay. Snook’s Bayside is a great choice.

Next stop: It’s an easy 25-mile or so drive to Islamorada (though it can take an hour if the traffic gods aren’t on your side).

Islamorada: 1 day  

Islamorada is pronounced nothing like it’s spelled (eye-luh-murr-AH-da), nor is it merely one isla, but rather five different islands. Start off by feeding the massive tarpon at Robbie’s Marina, then rent a kayak for a paddle out to Indian Key Historic State Park, an uninhabited island that was home to a thriving community back in the 19th century. Leave time for a nature walk at Windley Key Fossil Reef Geological State Park. 

Next stop: The views just keep getting better - especially as you cross aptly named Seven Mile Bridge - en route to Bahia Honda State Park (a one-hour drive). 

Bahia Honda State Park: 1 day 

The Keys aren’t known for their beaches, making the white sand shoreline of Bahia Honda all the more glorious. Enjoy some downtime by the water, or get active renting kayaks or walking an old section of the former rail bridge. 

Detour: Tack on an extra half day with a visit to Big Pine Key, which has a large reserve full of tiny Key deer, an endangered subspecies of white-tailed deer. Get info and pick up trail maps at the National Key Deer Refuge Headquarters.

Next stop: You’ll cross more islands and enjoy plenty of water views in both directions before reaching Key West (another hour or so). 

Key West: 1 day 

Celebrate the Overseas Highway adventure at Key West. Though it’s the end of the road, the vibrant, bohemian-loving enclave is the starting point for loads of other activities and adventures. Walk in the steps of a literary giant at the Hemingway House, see treasures unearthed from the deep at Mel’s Maritime Museum and catch the sunset amid the buskers on always-lively Mallory Square.  

Detour: Add on another day with a visit by boat or seaplane to the Dry Tortugas National Park, a small island fringed by coral reefs.

2. Southern charm in Georgia and the Carolinas 

8-day itinerary
Distance: 540 miles (869km)

You’ll see plenty of dramatic scenery on this coastal road trip that takes in historic cities, barrier islands and wild beaches. The lovely backdrop is just one of the big draws. There’s also the mouthwatering seafood, the art scene and, perhaps most importantly, the friendly dose of southern hospitality you’ll experience throughout your journey.

Savannah: 2 days

Immerse yourself in the welcoming rhythms of the South in Savannah, one of its most captivating little cities. Check out artwork at the Jepson Center for the Arts, designed by the great Moshe Safdie. Take in the beauty of Cathedral Basilica of St John the Baptist, and unwind under the Spanish moss-draped live oaks in Forsyth Park. Savannah has some excellent restaurants, try the upscale southern classics at the Olde Pink House.  

Next stop: Beaufort is around 43 miles north; allow just over an hour to get there. 

Beaufort: 1 day 

Sitting pretty on Port Royal Island, Beaufort (pronounced "byoo-furt") is South Carolina’s second oldest city and a good place to learn about Gullah culture. The downtown riverfront is sprinkled with art galleries and cafes, and offers a dose of late 19th-century history at the Reconstruction Era National Historic Park. 

Next stop: It’s a 70-mile drive northeast to Charleston (about a 90-minute drive). 

Charleston: 2 days 

Delve into the downtown of Charleston, wandering the Historic District’s cobblestone and brick alleyways and touring over-the-top mansions like the Heyward-Washington House. Don’t miss the International African American Museum, which has thought-provoking galleries that take visitors on a journey from ancient Africa to the present day. 

Detour: Break up your drive to the Outer Banks with a stop in Wilmington, with its restaurant-lined riverfront and inviting beaches nearby.   

Next stop: Set out early for the 8½-hour journey to Ocracoke on the Outer Banks, which includes a ferry trip from Cedar Island. 

Outer Banks: 3 days  

Stretching for more than 100 miles off the North Carolina shore, the Outer Banks are a series of narrow islands fringed by sandy beaches and dotted with attractive, centuries-old townships. You can explore by road, with vehicle ferries getting you between islands, along the Outer Banks Scenic Byway. A good base is Ocracoke, with its beaches and  historic sites - including the Ocracoke Preservation Society Museum and the British Cemetery. You can also explore a ghost town at Portsmouth Village, learn about the lost colony of Roanoke at Fort Raleigh National Historic Site, and hike the sandy hills of Jockey's Ridge State Park on Nags Head. 

3. Circle the Chesapeake Bay: Maryland, Delaware and Virginia

6-day itinerary 
Distance: 550 miles (885km) 

It’s the nation’s largest estuary and the watery backyard for more than 18 million people. It’s also the source of seafood riches (namely blue crabs, oysters and rockfish) and a gorgeous backdrop to boating adventures. We’re talking of course about the Chesapeake Bay. Travel here takes you through bayside villages, captivating big cities and frozen-in-time settlements that predate the creation of the US. You’ll also see Atlantic beaches, wild horses and one very famous presidential home.   

Baltimore: 2 days

Delve into "Charm City" taking in the attractions of the Inner Harbor starting with the impressive National Aquarium. See outsider art at the fabulous American Visionary Art Museum and have dinner in the cobblestone district of Fells Point. 

Detour: Visit Annapolis, Maryland’s historic state capital, and a prime spot for sailing trips across the Bay.

Next stop: Take the soaring 4.3-mile Chesapeake Bay Bridge across to Maryland’s Eastern Shore and continue to Rehoboth Beach (a 2½-hour drive). 

Rehoboth Beach: 1 day

Welcome to Delaware! Greet the sunrise with an early morning stroll along the sandy shore of Rehoboth Beach, which is an attractive town dotted with Victorian houses and fringed by ponds and nature reserves. After some beach time, walk the wide planks of the boardwalk, stopping for carnival amusement at Funland. 

Next stop: Head south to Chincoteague Island, which is just less than a 2-hour drive. Along the way, you’ll pass back into Maryland and then into Virginia. 

Chincoteague: 1 day

Near the southern end of the peninsula sometimes dubbed Delmarva (DELaware-MARyland-VirginiA - since three states all claim a part of it), Chincoteague is a peaceful little town overlooking the Chesapeake Bay. The big draw is the herd of wild horses that roams the island. You can also catch some fiery sunsets, best enjoyed with an ice cream cone from Island Creamery. 

Next stop: It’s about a 3-hour drive to Williamsburg, and you’ll cross the Chesapeake once again, this time driving under the waterway, via the 17.6-mile Chesapeake Bay Bridge-Tunnel. 

Williamsburg: 1 day

Feel the clock spin back a few centuries in Colonial Williamsburg, a living history museum that transports visitors to the 1700s. There’s much to explore in this 300-acre park, with costumed interpreters practicing trades as apothecaries, blacksmiths, printers, soldiers, bartenders and patriots. You can even dine on authentic recipes of yesteryear at places like the King’s Arms Tavern.  

Detour: Add another day (or more) in Richmond, Virginia’s capital, where museums like the American Civil War Museum-Historic Tredegar shed light on the Civil War. You can also tour Gilded Age mansions like Maymont.  

Next stop: It’s another two hours to Alexandria, just across the Potomac River from Washington, DC.  

Alexandria: 1 day

Red-brick colonial homes, gas lamps and cobblestone lanes set the scene for an atmospheric wander in the Old Town of Alexandria. Yet, this is no time capsule like Williamsburg but a vibrant town, with an impressive art scene (check out the Torpedo Factory Art Center), live music (catch a show at the Birchmere) and some memorable restaurants (book a table at the venerable Gadsby’s Tavern).

Detour: It’s a short hop down to Mount Vernon, the former estate of George Washington, and it’s worth taking a tour of the house and grounds.

Extension: Take the metro to travel between Alexandria and Washington, DC. And you could add on a few days to take in the Smithsonian museums and government buildings. Otherwise, it’s a little more than an hour’s drive from Alexandria back to your starting point in Baltimore.  

4. Islands, Capes and Seashores: exploring coastal Massachusetts

On this sea-going journey in Massachusetts, experience grand waterfront towns and picturesque beaches, not to mention two of New England’s most entrancing islands. Even when you’re not boating or frolicking in the waves, the sea plays a starring role here at venerable restaurants and museums.

9-day itinerary
Distance: 210 miles (338km)

Boston: 2 days

New England’s largest city is well-known for its arts scene, cuisine and historic sites. Spend day one walking the Freedom Trail, followed by an Italian feast in the North End (Mamma Maria is a great option). On day two take the boat out to Georges Island for a wander through an eerie 19th-century fort.

Detour: Catch the train to Salem for a half-day learning about the witch hysteria of the 17th century.

Next stop: Buy a ticket to the fast ferry for the 90-minute ride to Provincetown.   

Provincetown: 1 day

Enjoy one of the most exciting destinations on Cape Cod. Take a whale watching tour, visit the curious Dune Shacks along the Cape Cod National Seashore and partake in LGBTIQ+-fueled nightlife in vibrant Provincetown. After a day of outdoor adventures, treat yourself to a meal of fresh-off-the-boat seafood at the Lobster Pot. 

Next stop: It’s a two-hour bus trip (or one-hour drive if you have a car) to Chatham.

Chatham: 1 day 

Spend a day soaking up the life aquatic in charming Chatham. Look for seals at the Chatham Fish Pier and have a bite at the Chatham Fish Market. After lunch enjoy some time in the surf on Lighthouse Beach. Later in the day, join birdwatchers at the Monomoy National Wildlife Refuge and keep an eye out for dolphins, whales and other marine life.

Next stop: Allow about 80 minutes for the bus ride (35 minutes by car) to reach Hyannis. 

Hyannis: 1 day

On the south side of Cape Cod, Hyannis was once a favorite destination of President JFK. Get your fill of presidential lore at the John F Kennedy Hyannis Museum, then have a peach ice cream (Jackie’s favorite flavor) at Four Seas Ice Cream. In the afternoon, go sailing – make it the Cape Cod Pirate Adventure if you have kids in tow.

Next stop: It’s a one-hour ferry ride from Hyannis to Martha’s Vineyard. 

Martha’s Vineyard: 2 days

It’s easy to fall for the enchanting island of Martha’s Vineyard. After the ferry from Hyannis, head to the Aquinnah Cliffs, dramatically set above the crashing waves. Continue to Gay Head Lighthouse for more Instagram-worthy pics, followed by some downtime on secluded Moshup Beach. On day two, visit Oak Bluffs to see the colorful Gingerbread Cottages, go for a sailing trip aboard Black Dog’s Alabama, then cap the day with dinner and cocktails at Nancy’s Restaurant.

Next stop: You’ll hop across to Nantucket, a 75-minute ferry ride from Martha’s Vineyard.

Nantucket: 2 days

Start off by exploring the cobblestone streets of pretty Nantucket Town, and learn about this island’s seafaring roots at the Whaling Museum. Grab a bite and then head to the coastal village of Siasconset. Leave time for a seaside saunter on the ’Sconset Bluff Walk, meandering between grand homes and the roaring Atlantic. End the evening over local craft beers at Cisco Brewers.

5. Cities & Woodlands: riding Amtrak’s Vermonter from DC to Burlington 

10-day itinerary
Distance: 611 miles (983km)

Forget about the hassles of driving on this 10-day rail trip from Washington, DC, to northern Vermont. You’ll see vibrant city neighborhoods and idyllic countryside – not to mention riversides, hallowed art museums and one massive lake (the largest in New England, in fact). Come in spring for wildflowers, or in fall, when fiery colors blanket the hills and mountains northeast of New York City. 

Washington, DC: 2 days

Hit the ground running in the nation’s capital. Check out the monuments and memorials on the National Mall. Visit stellar museums like the National Museum of African American History and Culture, and enjoy neighborhood exploring in Georgetown and Dupont Circle. 

Next stop: It’s just under two hours for the morning train ride to Philadelphia.  

Philadelphia: 2 days

Take a deep breath and pound up the 72 steps, Rocky Balboa-style, of the Philadelphia Museum of Art (then check out the outstanding collection inside). Or skip the theatrics and delve instead into America’s revolutionary past at the Independence National Historical Park. 

Next stop: It’s about a 90-minute rail journey to New York City. 

New York City: 3 days 

Lace up your walking shoes and hit the pavement in New York City. Work your way up Manhattan, stopping for dim sum in Chinatown, shopping in SoHo and a meander along the High Line in West Chelsea. Leave time for a leisurely stroll across the Brooklyn Bridge (preferably around dawn when the views are magical and the crowds are thin). And enjoy some nature time in Central Park. 

Next stop: Have a leisurely breakfast (bagels and lox at Russ & Daughters?) then catch the train to Northampton, a 4½-hour ride from NYC.   

Northampton: 1 day

Welcome to New England! Northampton in central Massachusetts, is a vibrant college town with an intriguing past (once home to transcendentalists and abolitionists). Have a wander through the leafy campus of Smith College, then hit the town’s galleries, bookstores and record shops. It’s also worthwhile renting a bike for a spin through fields and forests on the Norwottuck Trail.   

Next stop: You’ll leave Massachusetts behind and cross into Vermont on the one-hour train ride to Brattleboro.

Brattleboro: 1 day

The southern Vermont town of Brattleboro has a bohemian, art-loving soul. See the latest exhibitions at the Brattleboro Museum and Art Center, then take a hike into the wilderness just out of town. A few favorites are the trail to Retreat Tower or the ascent up Wantastiquet Mountain, just across the Connecticut River in New Hampshire. 

Next stop: The views grow more bucolic on the 3½-hour ride north through Vermont to Essex Junction-Burlington Station. 

Burlington: 1 day 

Overlooking Lake Champlain, Burlington is one of Vermont’s most captivating little cities. Take a boat ride onto the lake aboard the Spirit of Ethan Allen or admire the view across the water while walking, running or cycling along the Burlington Greenway. Don’t leave town without a stroll along Church St, home to the firehouse-turned-art gallery of Burlington City Arts, sweets shops like Lake Champlain Chocolates and arts and crafts galore at Frog Hollow Vermont State Craft Center.

Detour: Keep riding the Vermonter another half hour to the end of the line in St Albans, a sleepy town with wondrous nature nearby, best accessed on the 26-mile Missisquoi Valley Rail Trail.

6. Lobsters and Lighthouses in Maine 

7-day itinerary
Distance: 298 miles (480km)

Maine is synonymous with maritime beauty: picture rocky undulating coastline battered by frothy seas, with a lone lighthouse glimmering off in the distance. This journey from Portland to the edge of New Brunswick, Canada, follows Hwy 1, which hugs the coast for much of the time. You’ll wind past seaside villages and scenic headlands, with mesmerizing views over the water. Plus, there will be plenty of opportunities to get your fill of lobster at wharf-side shacks along the way. 

Portland: 2 days  

Hear the cry of gulls overhead as you wander the atmospheric brick lanes of the Old Port district in picturesque Portland. Browse for made-in-Maine crafts at Lisa Marie’s, pick up an eye-catching tote made from a former sail at Sea Bags and enjoy a seafood feast at Scales. 

Detour: Head to Cape Elizabeth for fine views from Fort Williams Park, which is also home to the much photographed Portland Head Light.

Next stop: It’s a 75-minute drive to Boothbay Harbor, though the trip could take a lot longer if you stop along the way at the outlets and shops (including Maine icon LL Bean) in Freeport.  

Boothbay Harbor: 1 day

Set at the end of a narrow peninsula, Boothbay Harbor makes a fine base for aquatic adventures. Head out on a kayaking excursion with Maine Kayak. Later, head to the area’s woodlands, enjoying a walk in the lovely Ovens Mouth Preserve.

Detour: Catch the ferry to remote Monhegan Island, which feels like a vestige from the 19th century. While there, be sure to walk the cliff trail and drink an IPA from Monhegan Brewing Company (Maine’s tiniest craft brewer).

Next stop: It’s another one-hour drive up the coast to Rockland.  

Rockland: 1 day 

The vibrant town of Rockland dates to 1769 and is best known for the excellent Farnsworth Art Museum. Stretch your legs and get an eyeful of more lighthouse allure at Rockland Breakwater Lighthouse. If you’re here in early August, be sure to visit the Maine Lobster Festival. Otherwise, stop in Archer’s on the Pier for an anytime lobster feast.  

Next stop: You’ll get some fine panoramas over Penobscot Bay as you make the 2-hour drive to Bar Harbor. 

Bar Harbor: 2 days 

The picturesque village of Bar Harbor is a delight to explore with its walkable center full of galleries and views over the water. Learn about indigenous culture at the Abbe Museum. At low tide, you can make the 0.4-mile walk over a gravel bed to Bar Island. Bar Harbor is also a great base for exploring Acadia National Park in its backyard. Hike (or drive) to the top of Cadillac Mountain, walk through the surf at Sand Beach and go for a scenic drive along Park Loop Rd. 

Detour: It’s about a 30-minute drive across Mt Desert Island to Thurston’s Lobster Pound, a fabulous but casual spot for munching on lobsters.  

Next stop: Allow about 2½ hours for the drive to Lubec.  

Lubec: 1 day

East of Bar Harbor, the population thins considerably. You'll have the road mostly to yourself as you make your way to tiny Lubec, the last stop before Canada. Spend the day in Quoddy Head State Park, with its rugged shoreline trails and a candy striped lighthouse, then toast the week’s adventures at Lubec Brewing Co.