- 1 / 10
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—like 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 near on the especially pretty outer Cape in Eastham. We recommend the airy nautical cottage that overlooks Wellfleet Bluff that made its way onto our list of the best Airbnb beach houses.
- 2 / 10
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.
- 3 / 10
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. We recommend Kermit’s Key West Key Lime Shoppe.
Where to stay: Spend the night tucked away from the hustle and bustle on neighboring Stock Island at The Perry Hotel Key West, where first-floor rooms have direct pool access and great on-site dining gives you a reason to stick around the property.
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- 4 / 10
Connecticut to Rhode Island
Another manageable New England road trip at just 100 miles, this drive takes you from New Haven, Connecticut, to Newport, Rhode Island. All you have to do is follow US-1 and hug the coast. This journey is a cinch for Bostonians and New Yorkers alike, and is chock-full of underrated pizza, scenic cliffs, and, of course, mansions.
Where to stop: When you stop in Newport, head to the cliff walk, a light and breezy 3.5-mile hike with panoramic bay views and sights of the Vanderbilt estate known as the Breakers, among other Gilded Age mansions.
Where to eat: Fuel up at the start of your journey in New Haven with an infamous famed clam pie featured on the first episode of Ugly Delicious from Frank Pepe. The accolade-racking pies are worth the wait.
Where to stay: If you’re itching to splash out, look no further than the Chanler at Cliff Walk in Newport, which landed on our 2019 Readers' Choice Awards. We’re partial to the Martha’s Vineyard villa, with its ocean view and canopied four-poster king bed.
- 5 / 10
Mid Coastal Maine: Portsmouth, New Hampshire to Camden, Maine
There’s nothing like a northern New England coastal drive, dotted with impossibly quaint seaside villages. From Massachusetts through New Hampshire, and all the way up to Maine, roll past endless beaches and fishing harbors, artists’ colonies and historic districts.
Where to stop: Portland. Though Maine's is the smaller and lesser-hyped Portland, it’s become a hot foodie city where lots of young chefs—alumni of bold restaurants in New York—have gone to open their own first spots.
Where to stay: Wentworth by the Sea in Portsmouth is a Marriott resort in a grand historic waterfront setting.
- 6 / 10
Savannah, Georgia to Charleston, South Carolina
Take in all the southern charms sandwiched between the South’s two most iconic cities by taking US-17, where roadside cherry-cider stands and vast horse farms mix with war relics and towering oak trees. Continue past Charleston proper to the serene beaches of Sullivan Island.
Where to stop: Stop at lesser-known historic site Sheldon Church Ruins, the remains of a circa-1753 church set ablaze first by the British during the Revolutionary War and then by the Union Army during the Civil War.
Where to eat: Discover why Charleston is such a foodie hotspot at The Ordinary, an exceptional oyster and seafood hall by James Beard winner Mike Lata, housed in a reinvented 1920s bank. Also, consider sister restaurant Fig, which stands for Food Is Good.
Where to stay: Stay in the center of Charleston’s historic district at Planters Inn, a boutique spot of Relais & Chateaux pedigree that houses 64 guest rooms, the acclaimed Peninsula Grill restaurant, and a champagne bar that serves rare vintages.
- 7 / 10
Many New Yorkers will tell you that the Hudson Valley makes for a great trip no matter how much time you have to spend—a day trip, short and sweet overnight, or weekend getaway from the city, you name it. Zip upstate on I-87 and meander through Beacon, Kingston, and Hudson. These destinations can be a road trip on tracks, too. Just hop aboard the Metro North.
Where to stop: A favorite Hudson Valley attraction is Storm King, a 500-acre sprawling lawn where you’ll find sculptures galore and more in an outdoor museum.
Where to eat: Backbar may look like an antique garden shop, but it’s actually a bar. The creation of Zak Pelaccio (formerly of Manhattan’s Fatty Crab) is worth driving two hours to Hudson for the kimchi and tequila-spiked-slushies it slings.
Where to stay: Make a home base in Kingston at Hotel Kinsley, which is housed in a former State of New York bank building and offers high design in a low-key environment.
- 8 / 10
Blue Ridge Parkway: The Great Smoky Mountains
The Blue Ridge Parkway is America’s longest linear park, running 469 miles through 29 counties in Virginia and North Carolina. The picturesque road is hugged by the soft green valleys that descend from the Blue Ridge Mountains, and often clouded by a heavy mist that can fall over the area in the early morning or at sunset—so drive with caution.
Where to stop: Dollywood at Pigeon Forge. Embrace the camp and just go—trust us on this one.
What to eat: Stop off at Benton’s Smoky Mountain Country Hams to try hams that are slow-cured and aged nine to ten months.
Where to stay: Stay like a Vanderbilt at the Inn on Biltmore Estate, a formal and upscale affair just outside of Asheville, North Carolina.
- 9 / 10
The Cabot Trail
Okay, this one's going to mean crossing a border, but the minor inconvenience is well worth it. Head north—way north—to the tip of Atlantic Canada for the 185-mile Cabot Trail, a highly rewarding loop through the wilds of northeastern Nova Scotia, hugging the craggy coastline of Cape Breton Island and traversing the canyons and valleys of Cape Breton Highlands National Park. The well-marked trail is dotted with small towns, fishermen villages, lighthouses, and pubs as colorful as the locals. (Note that as of publishing, the U.S.-Canada border is closed until August 21.)
Where to stop: Stop in Chéticamp for the once-in-a-lifetime opportunity to swim with pilot whales. Captain Zodiac has the exclusive permits to snorkel with these highly intelligent creatures and responsibly interact with them under-water.
Where to eat: Grab a seat on the oceanfront patio, and feast on fresh lobster rolls or pan-fried haddock and scallops at no-frills Seagull Restaurant in Ingonish.
Where to stay: Unpack at the 72-room, waterfront Cabot Links Lodge. Golf enthusiasts will appreciate its world-renowned courses, but non-golfers can simply enjoy the views and comforts of the most modern accommodation in all of Cape Breton.
- 10 / 10
A1A: Miami Beach to St. Augustine, Florida
Florida State Road A1A is a patchwork of coastal highway along much of the state’s scenic Atlantic coast, alternating between the mainland and narrow barrier islands. Enjoy the best bits of this 339-mile highway, starting at the Art Deco-lined beachfront of South Beach, Miami, and inching up to the wide, sparkling beaches of Fort Lauderdale. Gawk at the mansions of tony Palm Beach and later cross over to the nature-steeped environs of Vero Beach and Merritt Island, where birds and manatees rule. End at the nation’s oldest city, Spanish-influenced St. Augustine.
Where to stop: In Vero Beach, get in the passenger’s seat for a seaplane ride over the most biodiverse lagoon ecosystem in the Northern Hemisphere, Indian River Lagoon. Spot loggerhead sea turtles, bald eagles, alligators, and manatees from above, before a water landing in Blue Cypress Conservation area. Treasure Coast Seaplanes offers scenic flights daily.
Where to eat: When you’re in Fort Lauderdale, sip on rum cocktails and feast on beach-focused cuisine at chic waterfront restaurant, Burlock Coast Seafare & Spirits.
Where to stay: In St. Augustine, book a room at The Collector Luxury Inn & Gardens, a 30-key adaptive reuse of late 18th-century homes (formerly preserved as the Dow Museum of Historic Houses).
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