The Ultimate New England Road Trip: 5 Destinations You Can’t Miss The Friendly Traveler

New England is one of the most charming areas in the United States, known for it’s many coastal towns, islands, small-town Americana, and history. This itinerary covers all my recommendations for where to visit on a New England, East Coast road trip. The itinerary starts in Boston, which is an easy and affordable city to fly in/out of which was important since I was visiting from California. It then highlights the region’s most iconic destinations – perfect for a 7-10 day trip.

Stop 1: Boston, Massachusetts

Boston is a beautiful and historic city that is worth dedicating a few days to exploring to start your trip. It’s also a very accessible city, I recommend waiting to get a rental car until the end of your time in Boston. These are some can’t-miss activities while in Boston:

Historic Freedom Trail
Stroll through Beacon Hill
Attend a Redsox Game at Fenway Stadium
Explore Boston Common & Public Garden
Visit the North End (Little Italy)

Stop 2: Cape Cod, Massachusetts

Cape Cod is an absolute must as your first stop out of Boston. The iconic summer beaches, lighthouses, and seafood shacks make this such a special part of New England. Some highlights to have on your list:

Provincetown
Catham
National Seashore

There are ferry connections from here to Martha’s Vineyard & Nantucket which make it easy to reach your next destination!

Stop 3: Martha’s Vineyard & Nantucket

From Cape Cod, you’ll be able to take the ferry from Woods Hole, MA. The only way to get to either of these islands is via Ferry as there are no bridges connecting them to the mainland. You can buy a vehicle pass to get the ferry to transport your vehicle with you, however, public transportation is very convenient on the islands so I recommend just buying a passenger ticket. Some highlights for your time here:

Edgartown, MV
Oak Bluffs, MV
Brant Point Lighthouse
Downtown Nantucket

For more information on how to get around and what to do in Martha’s Vineyard, check out my all-in-one guide here.

Stop 4: Newport, Rhode Island

Once you get back to the ferry stop in MA, it’s about a 1.5 hour drive from here to Newport, Rhode Island which is another must-see coastal town in New England. I found that Rhode Island had the most historic feel to the city, with some of the oldest taverns and town buildings still standing and running. Some key highlights:

Cliff Walk
The Newport Mansions
Thames Street & Downtown Waterfront
Ocean Drive (Ten Mile Drive)
Bowen’s Wharf

I would actually recommend having the shortest amount of time in Newport. We had two nights, but I think you can see everything you want to see with just one night here and two full days if you get an early start to the day from Martha’s Vineyard/Nantucket.

Stop 5: Mystic, Connecticut

Mystic is a cute, small coastal town about an hour south of Newport. I recommend doing a beach day here and then enjoying the charming downtown for a night. It has a very local feel to it with many storefronts to window shop through.

Bonus: Drive 2 Hours South to New York City

I also stayed a few days in New York City while doing this trip because it’s hard to go all the way to the East Coast and not visit my favorite city. If you decide to add NYC to the itinerary, I highly recommend booking this as a multi-way flight so that you can fly out of JFK versus needing to backtrack back up to Boston which is a few hour drive.