Coastal Maine Travel Itinerary: Bar Harbor, Kennebunkport and Portland
There’s just something about Coastal Maine. The crisp morning sea breeze, locals willing to break bread with strangers and restaurants showcasing dishes made with some of the freshest seafood. Last month I ventured out on a 5-day road trip through Coastal Maine and learned why Mainers and tourists alike rave about. Coastal Maine has a lot to offer, and I hope by 5-day Coastal Maine travel itinerary will inspire you to venture to one of the greatest American coastlines.
Below you’ll find my Coastal Maine travel itinerary to Bar Harbor, Kennebunkport and Portland.
If you’re flying into Boston, be sure to also check out my guide to Boston, too!
Is this the best road trip in Maine?
This could possibly be the best road trip for a quick trip through Maine. You get to see some great sites, good eats along the coast, and all the best highlight towns along the way, too. The trip will take you along the coast, so you can enjoy the scenery at your own pace.
Trip Highlights
Day One: Boston Airport and Bar Harbor
Our trip in Maine started at the Boston International Airport. Flying into Boston saved us about $300 on airfare. After getting our rental car we started the almost 6-hour drive up the Maine coast to Bar Harbor.
We arrived to Bar Harbor around 4:00pm and checked into our hotel, the Bar Harbor Manor. Bar Harbor has very few chain hotels, and the ones we saw were outside of the city limits. But walking down the streets of town, you’ll find many unique inns, bed and breakfasts, and small, independently owned hotels.
Travel Tip! You can earn points with my favorite Hotels.com hack on your boutique hotel stay in Bar Harbor.
We got into town just in time for dinner and our hotel recommended the Black Friar Inn and Pub. The Black Friar is definitely a place the locals go. Our hotel recommended ordering the blueberry mojito, made with wild Maine blueberries.
After dinner we stopped at another local favorite, Mount Desert Ice Cream. Maine is completely covered in ice cream shops, many of which offer some interesting flavor combinations (goat cheese and blueberries, sage and lemon). Mount Desert was excellent. The ice cream was super creamy and flavorful.
If you have time while in Bar Harbor, I recommend looking at some of the local shops downtown. We enjoyed browsing Sherman’s Book Store, Maine’s oldest operating bookstore, and I purchased an adorable stuffed alpaca for my soon-to-be niece or nephew at Peruvian Link.
Day 2: Visiting Acadia National Park
Acadia National Park sits to the south of Bar Harbor, and the park entrance was just four miles from our hotel. The entrance fee is $30 and covers access to the park for 7 consecutive days. It’s a must-stop on a Maine road trip!
The park has options for all different types of travelers, with a large driving loop around the park and pull-offs at scenic overlooks and attractions, like Jordan Pond and Thunder Hole. For those who like to trek on foot, Acadia also has some incredible hiking trails. We started our morning hike at the Beehive Trail, which starts right by the Sand Beach parking lot and ended up exploring the Bowl and Chaplin South Ridge trails in the process.
The Beehive Trail requires some climbing, and I don’t recommend it if you are uncomfortable with heights. But the way to the summit offers incredible views of Sand Beach, the Atlantic Ocean, and Bar Harbor. Make sure to bring plenty of water in a pack (the climb makes hand-held items pretty hard to carry) and wear hiking shoes.
We got back into town and hadn’t eaten since a breakfast sandwich from A Slice of Eden that morning. The evening before, the Black Friar recommended returning for their Happy Hour for half-price oysters and beers. And after six hours of hiking, we couldn’t say no to beer and oysters.
Days 3-4: Kennebunkport and Surrounding Towns
By Day 3 we had explored much of Bar Harbor. And although we could’ve done a couple more days at Acadia, our Coastal Maine road trip had us move on to Kennebunkport, the sleepy, coastal town made famous because of the Bush family in the 1980s. Kennebunkport was filled with rich retirees and richer residents but the downtown had a charm to it with rickety homes and shops on the river. Overall, we enjoyed Kennebunkport’s close proximity to other coastal communities, and since it took around an afternoon to explore Kennebunkport’s local attractions, we set out for the surrounding beach towns on the second day.
During our time in Kennebunkport, we stayed at the Nonantum Resort, located 0.7 miles from the main town strip. It was an adorable hotel on the river with adorandak chairs overlooking yachts and sailboats. A sweet place with friendly staff and good food and cocktails.
On the second day in Kennebunkport, we decided to adventure out to Ogunquit after learning about the Marginal Way, a scenic, coastal walking trail along a pristine coastline. After our walk, we stopped at The Beach Basket for a fresh sandwich. I highly, highly recommend their blueberry lemonade.
A final recommendation is the happy hour at the Boat House in Kennebunkport (happy hour is 3-6pm). They have an excellent selection of small bites, cocktails, beer, and wine, and the restaurant includes a wrap-around deck on the river and high-top seating.
Note: We took Route 1 from Bar Harbor to Kennebunkport through the coastal towns. We stopped to get a famous lobster roll at Red’s Eats in Wiscasset. The rolls they serve at Red’s are simple: bread, lobster and butter.
Day 5: Portland
Originally, we wanted to stay in Portland for one or both of the nights we ended up staying in Kennebunkport. Instead, we decided on Kennebunkport because it was considerably cheaper and only 25 miles from Portland, making it still convenient to explore the city. By far, Portland was our favorite town. Not only did it live up to its reputation as one of the best food towns in the United States, it surprised us with its turn-of-the-century architectural charm and friendly locals.
We had one goal when we got to Portland: eat everything.
We started our morning waiting in a line that I imagine is much longer on the weekends at the Standard Baking Co. downtown. When I was researching Portland, this place had rave reviews from small-town bloggers and magazines. And let me tell you, it did not disappoint. I’m still thinking about that sweet, chewy morning bun. We took our breakfast goodies out to the Portland Head Lighthouse, which offered a much better view than the parking lot. (Breakfast is always better with a view!)
We came back into town in time for lunch at the Portland Lobster Co. on the harbor. Mainers are going to give me heat for this, but it was probably my favorite lobster roll of the trip. It was light and refreshing but also a manageable size. Also try the fried clams if you get the chance.
Perfect afternoon in Portland, Maine
Next to the Portland Lobster Co., people were selling boat tours. Typically I avoid brochure stalls, but with nothing to do and tickets only $35 apiece for two hours of entertainment, we booked tickets on the Portland Discovery Land and Sea Tours. As skeptical as I was, it was one of the best experiences of the trip. We saw lighthouses and wildlife and learned a lot about Maine throughout it.
After the boat tour, we ended our “Kendyl and Aspen Eat Everything in Portland, Maine Tour” at Eventide Oyster Co. The restaurant is known for their brown butter lobster roll that’s served on an Asian-style steam bun. The roll lives up to the hype, but be warned it’ll set you back $18 in a couple of bites. All the small bites we got were delicious, but I especially loved their local oysters and cocktails.
After Eventide, we walked off our dinner by heading to a few local breweries. We had heard Portland had a good brewery scene and checked out neighboring businesses Austin Street and Rising Tide Brewing Co.
At the end of our foodie day in Portland, we drove back to Boston to do some sightseeing for a couple of days before flying home. It was, unfortunately, the end of our Coastal Maine travel itinerary.
Total Cost Breakdown
Accommodations: $480 Food: $495 Entertainment and Shopping: $220 Rental Car: $375 Airfare: $200 (we had travel credit) Total Cost: $1770 The Most Worth It: Portland boat ride ($70 for two); Black Friar Happy Hour oysters ($1.75 a piece); Acadia National Park ($30 entrance)
This was a pretty expensive trip for us. The cost of rental cars is soaring right now due to lack of supply from car companies. Though we spent under $100 a day for dining, we did indulge on a couple of splurges. Overall, $1770 in 5 days for two people traveling by air in the United States is a fair price.
Coastal Maine was a fantastic getaway. I usually don’t go to the same place twice, but I’m already looking forward to heading back. I hope my Coastal Maine travel itinerary can help you plan your own trip!
Explore on. – K
