Perhaps more than any form of travel, the road trip is stamped in the American imagination. And when it comes to road trips between the Atlantic and Pacific, no region is as underrated as the East Coast. Sure, it lacks the sprawl of the middle and west of the country, but the vast number of states, four distinct seasons, and an incredible range of cultures prove the East Coast is the coast with the most—and the only possible way to sample its infinite variety is behind the wheel. Here are 10 of my favorite East Coast road trip itineraries, including where to stop, where to stay, and what to eat along your drive.
CAPE COD PENINSULA Cruise up the curling bicep of Cape Cod via U.S. Route 6 for a New England road trip of wineries, whale watching, and restorative salty breeze. The highway stretches from Providence to Fall River to New Bedford through the Cape, but it’s those personality-filled Cape towns - from quaint Bourne to splashy Provincetown - that you’re driving here for.
Where to stop: Head to Truro Vineyards + South Hollow Spirits, just south of Provincetown, which is both a winery and a distillery that makes gin from juniper berries grown on-site. Where to eat: For a fancy classic, dine at the Chatham Bars Inn restaurant. The waterfront dining is on Chatham Harbor, offering those much-needed views and the premium quality seafood to match. The New England clam chowder is legendary. Where to stay: Plan to spend your nights on the especially pretty outer Cape in Eastham. I recommend an airy nautical cottage that overlooks Wellfleet Bluff.
VERMONT 100 Spanning more than 200 miles of idyllic New England countryside, this route takes you through countless Norman Rockwell-esque towns. Pass country stores and farm stands and explore the well-traversed stops of Wilmington, Ludlow, Killington, Warren, and Stowe.
Where to stop: Stowe Recreation Path is ideal for biking, hikes, and idle picnics. In Weston, give yourself a little time to browse around the Vermont Country Store (est. 1946) where you’ll find everything from old-fashioned fudge to seersucker pajamas. Where to eat: You can get casual authentic Mexican eats at the no-frills, local favorite Mad Taco (Waitsfield and Montpelier) and for something sweet and savory, try goat cheese with caramel sauce (yes, that’s right) at the family-run Fat Toad Farm in Brookfield. Where to stay: In Warren, check in to The Pitcher Inn, a stately-chic white house kitted out in a haute New England prep decor (think duck decoys and paneled walls). After a country breakfast, take out a complimentary canoe on the trout-filled stream or play a game of shuffleboard.
OVERSEAS HIGHWAY: MIAMI TO KEY WEST Florida’s Overseas Highway is a 127.5-mile highway that connects Miami to Key West. It’s about a four-hour drive across countless coral and limestone islets, so take your time and stop often to sightsee, picnic, kayak, or swim. Watch out for the Seven-Mile Bridge: Long and narrow, it will make you feel like you’re soaring over the water.
Where to stop: Stop in Tavernier to access the Conch Reef, a Sanctuary Preservation Area that’s rich with tropical fish and coral—perfect for snorkeling and shallow dives. Conch Republic Divers offers twice-daily reef and wreck dives. Where to eat: When you’re in the Keys, you need to get key lime pie, naturally. I recommend Kermit’