Last Updated on: 19th September 2021, 06:26 pm
Driving up the East Coast on a Philadelphia to Boston road trip is one of the great American road trips. A route straight through the history of the United States, and one packed full of vibrant, fascinating destinations and glorious scenery. Explore Pennsylvania, Connecticut, Rhode Island, and New Hampshire, and discover the best the East Coast has to offer!
This itinerary is perfect for someone flying into Philadelphia and out of Boston, or for someone based in Philadelphia who wants to go on a New England road trip.
Once in Boston, you can explore the city or you can continue on your journey up to New Hampshire and Maine. You can even take a cruise from Boston! Cruising from Boston is easy and gives you opportunities to turn your trip into a bucket list adventure!
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My Favorite Travel Booking Sites for 2023
These are my favorite companies that I use on my own travels.
Find cheap flights with CheapOair.
Find the best deals on hotels & vacation rentals on Booking.com.
For road trips and ground transportation, rent a car through Discover Cars.
Find information and cruise reviews on Cruise Critic.
For packing and travel essentials order via Amazon.
Store your luggage safely with Radical Storage.
Tips for Renting a Car in Philadelphia
While I have taken the bus from Philadelphia to Boston (as well as taking a flight), I think the best way to reach this great city from historic Philadelphia is by car. If you are starting from Philadelphia but don’t have a car, I suggest renting one in Philadelphia. You can drop it off in Boston and then fly home if you don’t want to drive the route back.
If you’re also looking to rent a car, I use Discover Cars when I rent cars on my travels. You’ll be able to pick up a car at any airport or in your hometown.
Check availability and get a quote for a rental car for your trip here.
Philadelphia to Boston Road Trip Itinerary
Here’s my idea of a fabulous road trip from Philadelphia to Boston.
Days 1-3: Philadelphia, Pennsylvania
I lived in Philadelphia for ten years, and I absolutely adore it! So much so that I’ve gone back to do real Philadelphia vacations twice in the five years since I left. However, if you’re from Philadelphia, feel free to skip this part of the itinerary and just add an extra day to Mystic and Boston (or two extra days in Boston).
Spend your first two days exploring Philadelphia. The City of Brotherly Love is an underrated destination. A lively, quirky urban center with an astonishingly rich history and a fantastic dining scene, it is well worth taking a little time to get to know Philly.
Check out the Liberty Bell and Independence Hall to get a real taste of the foundation of this country, and indulge your cultural urges at The Philadelphia Museum of Art or African American Museum. And don’t miss the chance to eat a genuine, authentic Philly cheesesteak!
You can easily spend two days just exploring Old City, but I suggest at least spending part of your time in South Philly! South Street is always fun, especially if you’re looking for something to do in Philadelphia at night!
On day three, it’s time to start your road trip. You can pick up your rental car now if you haven’t already.
Once you hit the road, you could easily just barrel up I-95 and make to our next stop in under five hours. But where would be the fun in that? Head west and check out Valley Forge, where Congress fled when the British invaded Philadelphia before heading out of state.
Day 4-5: Mystic, Connecticut
One of the prettiest places in Connecticut, Mystic is famous for more than just its pizza, though of course you can always get a slice and enjoy a rewatch of the movie in your hotel room after exploring the town!
Besides being home to one of the prettiest lighthouses on the East Coast, you can also visit the Mystic Aquarium and the Dennison Homestead. You will want to stroll Main Street to enjoy the charm of the town itself. If you want to get out on the water, there are lots of ways to enjoy Mystic’s waterways. Why not start by going on a Sabino Steamboat tour?
Day 6-7: Providence, Rhode Island
On your way to Providence, Rhode Island, you can keep taking the fast (but inland) I-95 or switch to the longer but coastal Route 1 with the wild Atlantic on your right and an abundance of cute towns and villages to explore along the way. This is my personal preference, as I love taking scenic drives, but either option will get you to your destination.
Providence itself is worth exploring, home to the Rhode Island School of Design, Brown University, and some delightful 18th- and 19th-century architecture. A night here is enough to get a taste, but if you have extra time, you can explore further afield.
Day 8-10: Boston
The final stretch of the trip takes you through the charming countryside of Massachusetts, and finally to the buzzing, energetic, and historic city of Boston. Wompatuck State Park is worth a detour en route, but you will want to leave yourself plenty of time to explore the city as well.
Walk the Freedom Trail on a self-guided tour of some of the nation’s most significant historic moments, and check out the view of the city from Bunker Hill. Grab a bowl of chowder at Faneuil Hall market, and explore the picturesque waterfront and cobbled streets of the historic center. Finally, if you have time, a trip to Boston wouldn’t really be complete without catching a ball game at the iconic Fenway Park. Bonus points if you can wangle a selfie up on the Green Monster!
What to Pack for the East Coast
The Lonely Planet Philadelphia and Lonely Planet New England guidebooks. It can be kind of a pain to find the major guidebooks once you land, or you’ll find them overpriced. I always like to pick mine up ahead of time.
An Unlocked Cell Phone so that you can use a local sim card while here to help navigate public transportation and when you’re on the road. (For people without American cell phone plans).
Backup Charging Bank for your cell phone since you’ll be using it as a camera, GPS system, and general travel genie.
A Great Day Bag so you can carry what you need with you (like your camera, snacks, water, sunscreen, cash, etc). My current favorite is the Pacsafe Citysafe, which is especially great for the East Coast because it has many anti-theft features designed to deter pickpockets. It also transitions to a night bag more easily and won’t embarrass you if you go to dinner directly after sightseeing all day.
Don’t Forget About Travel Insurance!
Before you leave for your trip make sure you have a valid Travel Insurance Policy because accidents happen on the road. I pay for World Nomads, and I happily recommend them. It’s especially important to get travel insurance if you’ll be hanging out in large cities where pickpockets can pray on tourists.
I have been a paying customer of World Nomads for travel insurance for four years, and I happily recommend them. If you get sick, injured, or have your stuff stolen, you’ll be happy to have the ability to pay for your medical bills or replace what’s stolen or broken.