What You Need to Have on Your Boston to Maine Road Trip Itinerary

Mix things up every once in a while and venture out from your hometown to explore a nearby destination! We invite you to use that PTO you’ve been saving and experience the ultimate Boston to Maine road trip itinerary. Rather than book a flight, grab your friends or sweetheart and drive up the Atlantic coast. An endless list of adventures awaits! Stop to snap pictures at scenic lighthouses, indulge in local cuisines, and enjoy stunning waterfront views. Pack your bags, fuel up your car, and get ready for the trip of a lifetime.

If you need help filling up your Boston to Maine road trip itinerary, we have plenty of more recommendations in our free Vacation Guide. We included the absolute best things to do and places to see when you arrive in Maine. Get your guide now — you can even reference it while passing the time in the car!

Plan the Ultimate Road Trip

Your Boston to Maine Road Trip Itinerary

Why Midcoast Maine Is the Perfect Destination

If you’re coming from the Boston area, consider choosing Midcoast Maine as the final stop on your road trip. Boothbay Harbor is a scenic, waterfront village offering a relaxing escape from the hustle and bustle of the city. You can take a tour of several lighthouses, taste some of the freshest lobster in the country, go whale watching, and so much more. There are even some incredible places to stop along the way.

Travel Tips

To reach Boothbay Harbor from Boston, you can travel along I-95, I-295, and then Route 1 for a remarkable coastal adventure. From start to finish, you can expect about three hours of driving time over 168 miles. However, we highly recommend that you stop and experience some fantastic destinations along the way. Not only will this split up the drive and help avoid fatigue, but it adds additional opportunities for excitement and sightseeing!

Where to Stop During Your Journey

A skyline view of the Boston, MA, at sunset


If you haven’t been to Boston before, be sure to check out some of the historical sites along the renowned Freedom Trail. Depending on when you visit, you may also be able to catch a game or event at Fenway Park. This stadium remains an impressive landmark and attraction since its official opening in 1912.


About 45 minutes into your journey, stop off in Newburyport, MA. It’s a charming area filled with unique restaurants and shops to explore. When the weather is nice, you can also head to Plum Island nearby. Here, you can fish, kayak, birdwatch, or relax on the sandy shoreline. You can even enjoy a romantic dinner at the top of the Newburyport Lighthouse.

This beautiful waterfront community is home to the Kennebunkport Festival


From Newburyport, travel about 50 more miles north and rest in Kennebunkport, ME. It’s located on the coast by the mouth of the Kennebunk River. If you ask people that have visited before, they can tell you it’s well worth a visit while passing through. Take a break and let someone else handle the driving for a while by stepping aboard the Intown Trolley for a tour of the area.


If you’d like, you can also make a quick stop in Portland on your way to Boothbay Harbor. It’s the largest city in Maine and offers plenty of activities and attractions. Foodies will be happy to find several excellent eateries in the downtown area.

Aerial view of the area showing the things to do in Boothbay Harbor

Boothbay Harbor

The true Maine experience begins when you arrive in Boothbay Harbor. Our coastal village is home to a wide variety of attractions and things to do. Whether you’re searching for excitement or relaxation, there’s something for you here. To get a taste of our local culture, plan your trip around some of our festivals, like Windjammer Days and Boothbay Harbor Fest. If you’re not sure where to start and want to leave the planning to us, take a look at our five-day Maine itinerary!

The Best Place to Stay When You Arrive

The bed inside Room 15 in the Windward Guest House at Topside Inn

Topside Inn is a remarkable place to stay in Boothbay Harbor, but you don’t have to take our word for it. Read through some of our reviews and media mentions to see the type of experience and level of service you can expect. Our Inn features stunning views of the harbor, top-notch accommodations, and a long list of amenities like gourmet breakfasts with ingredients from our on-site gardens

Consider Room 15 for your relaxing getaway at Topside Inn. This recently remodeled space features a bright, modern feel in a coastal environment. Relax on your luxurious, king-size bed and enjoy unmatched views of the harbor and sunsets from your covered sitting porch. It’s the ideal place to end up on your Boston to Maine road trip.

Check our availability and book your stay today!