Road Trip Itinerary From New York City To Cape Cod

With its quaint villages and lighthouses, Cape Cod, Massachusetts, couldn’t be more different from the fast-paced urban hub that is New York City. Experience both with our road trip itinerary from New York City to Cape Cod, which leaves travelers with only one tough decision: windows up or windows down?

Overview

Total distance (approximate): 252 miles (405 km)

Total driving time (approximate): 4.5 hours

Recommended number of days traveling: 2

Experience New York City’s East Village

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).

Mural on Bleeker and Bowery in Manhattan

Empire State Building

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.

Casa Enrique

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.

Check in to the Delamar Greenwich Harbor

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.

Delamar Greenwich Harbor offers a full spa

Elm Street Diner

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.

Benefit Street

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.

Cape Cod

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.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.