An Iconic East Coast Road Trip From Maine to Florida's Key West

By Reade Tilley

There’s a lot of road along the East Coast between Portland, Maine and Key West, FL—nearly 1,800 miles of it, in fact. Following safety guidelines and driving no more than 500 miles at a stretch, you could make the trip in under four days—but why would you? Rather, here are five nicely spaced reasons to pull off the road and take a detour.

Portland, ME

Tick the box: Take a picture of the Portland Head Light, an iconic lighthouse built in 1791 at the direction of George Washington himself.

Detour: The Hayloft at Dragonfly Barn. With crystalline acoustics and a warmly intimate setting, this converted barn on an historic farm in Bridgton hosts a wide range of accomplished musicians, including locals and notables from around the country (and beyond). Singer-songwriters, classical ensembles, jazz, and more can be found here. Check the site for event tickets, book a room at the nearby Highland Lake Resort (every room has a lake view), and add a memorable evening to your road trip.

New York City

Tick the Box: Take a selfie on the top of the Empire State Building

Detour: Walk on The High Line. When NYC converted their elevated train tracks into a landscaped public park and walkway, few could have anticipated the appeal. More than 8 million people per year enjoy the intersection of art, design, and urban green space. Along the High Line, grab a cold beer and German nibbles (e.g. sausage, pretzels, and spätzle) at The Standard hotel’s ground-level Biergarten, but perhaps try The Jane for whimsical (and cost-effective) accommodations.

Virginia Beach, VA

Tick the Box: Walk the oceanfront boardwalk and get a pic of the King Neptune statue.

Detour: Be a barnstormer! Soar through the sky in a WWII-era biplane at the Military Aviation Museum. During the flight season from April through late October, 15-minute and 30-minute flights are available for this real—not virtual reality—ride in a thrilling open-cockpit two-winger, goggles and leather helmets included. If you’re a high flier on the ground as well, find your bed at the luxurious Cavalier Hotel (built in 1927), while travelers of most budgets should be happy with the oysters, seafood, and peaches Melba at Tautog’s Restaurant.

Charleston, SC

Tick the Box: Book a harbor tour and see Fort Sumter (among other historical sites)

Detour: Head to Forte Jazz Lounge for a charming mix of big-city sound and Southern hospitality. Candlelit tables, charcuterie, libations, and fantastic jazz talent are the recipe for a perfect evening, which can be capped off with a night at the French Quarter’s Loutrel hotel and then breakfast the next morning at the Flying Biscuit Café. 

Key West, FL

Tick the Box: Get a picture at the “Southernmost Point” buoy; bonus points if you stand on the south side of the buoy, technically putting you south of the marker meant to indicate the southernmost point in the continental United States. 

Detour: Fort Zachary Taylor Historic State Park, home to one of Key West’s best beaches (500 yards south of the “Southernmost Point” marker). If you’d rather hang in town, there’s a great little beach behind the Southernmost Beach Café—which has drinks and food that can be enjoyed on the sand. After sunset, the Thirsty Mermaid offers great dinner options (try the togarashi spiced yellowfin tuna or sautéed Bahamian conch) and a nice wine list.