Total distance (approximate): 252 miles (405 km)
Total driving time (approximate): 4.5 hours
Recommended number of days traveling: 2
Distance: 3 miles (4.8 km)
Travel time: 15 minutes
Manhattan’s East Village is famous, or perhaps infamous, as the epicenter of New York City’s punk counterculture during the 1970s. The neighborhood is still beloved for its anti-establishment vibe, complete with dive bars and graffitied walls. Experience the New York City shown on screen when strolling down the iconic St. Mark’s Place. Pick up a read for the road at the 1927-established Strand Books, boasting over 18 miles (28.9 kilometers) of books, and buy snacks from 24-hour Ukrainian diner Veselka (nothing too heavy though—lunch is just two stops away).
Distance: 2.3 miles (3.7 km)
Travel time: 21 minutes
When one of the world’s most famous buildings is only slightly out of the way, a detour is in order. Midtown Manhattan’s Empire State Building is an itinerary staple for a reason, or rather, reasons—the building has had starring roles in films like King Kong and Sleepless in Seattle, is the only New York City attraction with its own zip code, and accommodates a whopping 3.5 million visitors per year. Road trippers can add their party to that number when they take a brief detour to witness all 1,454 feet (443 meters) of the structure in person.
Distance: 3.1 miles (4.9 km)
Travel time: 23 minutes
As New York City’s only Mexican restaurant to earn a Michelin star, Casa Enrique could be a destination rather than a stop along the way. The casual eatery in Long Island City, Queens, is known for its steak tacos made with house-made thick corn tortillas as well as its chicken enchiladas in salsa verde. Order both, plus the Mole de Piaxtla and chile relleno.
Distance: 33.5 miles (53.9 km)
Travel time: 50 minutes
Get into a Cape Cod state of mind by keeping the rest of this journey light and breezy. One stop you may find difficult to leave is Delamar Greenwich Harbor in Greenwich, Connecticut. It comes recommended by Condé Nast Traveler and its readers—the hotel was rated one of New England’s best as part of the outlet’s 2016 Readers’ Choice Awards. Travelers (and their pilot’s driving foot) can rest in the hotel’s deep soaking tubs equipped with Bvlgari bath products and on hypoallergenic bed linens. Other amenities worth a slot on your itinerary include private in-room yoga lessons and complimentary seasonal harbor cruises on weekends.
Distance: 6.1 miles (9.8 km)
Travel time: 11 minutes
Breakfast is the most important and the most fun meal of the day at Elm Street Diner. One of many highly rated restaurants in Stamford, Connecticut, this family-owned diner excels at reminding road trippers they’re on vacation. Hearty peanut butter banana pancakes, breakfast quesadillas, homemade old-fashioned donuts, and coffee—lots of coffee—are just what drivers need for the long journey to our next stop in Providence, Rhode Island.
Distance: 142 miles (228.5 km)
Travel time: 2 hours 40 minutes
Consider the drive to Rhode Island’s most famous street the “road” phase of our road trip. Founded in 1636, Providence is one of the oldest cities in America, with a “Mile of History” to prove it. The state capital’s mile-long Benefit Street is an ideal place to stretch one’s legs thanks to the attractive historical homes which line it. See elegant Federal-era restorations and Victorian residences mixed in amongst Providence’s first mansion, the John Brown House, and National Historic Landmarks like the Governor Stephen Hopkins House. For history buffs and American patriots, pit stops don’t get more epic than this.
Distance: 72.5 miles (116.6 km)
Travel time: 1 hour 15 minutes
Traversing multiple bodies of water and the Rhode Island-Massachusetts border, the scenic 75-minute drive to Cape Cod puts the best of Northeast America on display. Here is where travelers take over. For example, beach lovers can continue driving to Cape Cod National Seashore, while adventurers can embark on a whale-watching expedition. And fans of the classics are only a brief journey from Cape Cod’s quintessential beach town, Chatham.