A Week Exploring Coastal Maine: The Ultimate Itinerary

One of the trips I am most frequently asked about is our trip to Maine this past fall. I finally took the time to put together the ultimate itinerary for a week exploring coastal Maine!

If you’ve never been to Maine before, you will be blown away by the charm that exists on every corner. It is quintessential New England – rocky shorelines with lighthouses, harbors filled with boats, and delicious buttery lobster rolls. We went in late September for our babymoon when I was 24 weeks pregnant, and it was perfect. It was the best mix of adventure, relaxation and sightseeing.

We started in Portland, moved on to Bar Harbor and Acadia National Park, then looped back down to Kennebunkport and Ogunquit. I promise you won’t be disappointed if you follow this itinerary – Charlie and I both agree that Maine is one of our favorite states we’ve ever been to. I can’t wait to go back!

Getting to Maine

We flew into Portland International Jetport late one night and rented a car at the airport. The airport is just 20 minutes from the city, so we drove directly to downtown Portland and checked into our hotel. Another option is to fly into the Boston Logan International Airport, rent a car, and drive up to Portland. This drive is about one hour and 45 minutes.

Getting Around Maine

We knew we wanted to rent a car so that we could explore more than just one town and really enjoy the coast of Maine. We rented our car from Hertz at the Portland airport and returned it when we flew back to DC.

Days 1-3 Exploring Coastal Maine: Sightseeing in Portland

Day 1: Portland Lighthouses, Lobster Rolls, Sailboat Cruise

We woke up and walked to The Holy Donut to grab donuts for breakfast. These potato donuts are by far the best I’ve ever had. I specifically recommend the coffee cake flavor. We took ours to-go, walked around the harbor and found a spot to sit and enjoy our donuts while watching the boats.

After, we drove to Portland Head Lighthouse and walked around the park there. We climbed some of the rocks and just sat soaked in the sound of crashing waves against the shoreline and the smell of the salty air. This was by far our favorite of all the lighthouses we saw. It was perfectly quintessential Maine.

Once we were done with the first lighthouse, we drove over to the Spring Point Ledge Lighthouse. This lighthouse was definitely less interesting than the Portland Head Lighthouse, but still cool nonetheless! This one involves a huge stretch of rocks that you can walk down to walk right up to the lighthouse. I definitely recommend good walking shoes.

We worked up quite the appetite after the lighthouses! We then drove to The Highroller Lobster Co. for lobster rolls. This was the first of many lobster rolls we had on our trip! Highly recommend adding the garlic mayo to your roll. We sat out on the back patio which was so cute.

After a big lunch at Highroller, we walked around the Old Port and explored all of the shops in the area (especially the ones on Exchange Street). There are so many artisan shops and clothing boutiques. Just spend some time getting lost in them! The Old Port is a quaint historic district with cobblestone streets and brick buildings. This is where we bought our baby girl her “Goodnight Maine” book, the first book we ever bought her 🙂

After bopping around the Old Port, we took a two-hour sunset sailboat cruise with Portland Schooner. This was a BYOB cruise around the Portland harbor. It was so fun chatting with the crew and learning all about the sailboat culture in Maine.

Once the sailboat cruise ended, we walked to Duckfat for an outdoor dinner. Put this on your list! They are known for their poutine and wow, it did not disappoint. I also highly recommend their tomato soup. Note: they do not take reservations and this place is very popular. Be prepared for a bit of a wait! I recommend grabbing a drink at the bar next door while you wait.

Day 2: Eastern Promenade, Spring Point Ledge Lighthouse

Sunday morning we woke up and went to Tandem Coffee. We ordered coffee and a breakfast sandwich to go. OMG, their breakfast sandwich was life changing!! I recommend ordering them online for pick-up early. They sell out, and once they are out, they’re out for the day.

We took our breakfast sandwiches to go and brought them to the Eastern Promenade for a little picnic on a park bench. This was incredible. It’s a huge waterfront hill/park and on a sunny day, there are boaters, kayakers, and people having picnics all around. We walked a couple miles up and down the shoreline.

When we were done walking, we found a spot on the big hill where there are tons of food trucks and laid out a blanket on the hill of the Eastern Promenade. We brought out our books and got Italian Ice at one of the food trucks nearby. There were so many other people laying on the hill reading their books or chatting with friends, it was so lovely!

That night, we had our favorite meal of the entire trip: dinner at Central Provisions. You need a reservation in advance for this restaurant. It was worth every bite. They change their menu on a regular basis, but if they have the Barcelona fries, bone marrow toast, or suckling pig, you NEED them. Ask for recommendations from their highly-knowledgeable wait staff!

After our early dinner, we got in the car, said our goodbyes to Portland, and headed to Bar Harbor for the next leg of our trip! It is about a three-hour drive from Portland to Bar Harbor, the home of Acadia National Park.

Where to Stay in Portland: We stayed at the Hyatt Place Portland – Old Port. We were very happy with the location – it is in walking distance to most everything we wanted to explore!

Days 4-6: Exploring Bar Harbor and Acadia National Park

Day 4: Bar Island, Acadia National Park

We woke up this morning and planned to walk to breakfast and then make our way to Acadia National Park. On our walk to breakfast, we saw a bunch of people walking in the same direction and we were curious where they were going. Right next to our hotel was Bar Island.

For 1.5 hours before and after low tide, a gravel bar is exposed connecting Bar Harbor and Bar Island. During this time, you can walk across the water and cross over to Bar Island to explore the hiking trail there. We loved this! Just be careful about timing – if you walk over to the island and lose track of time, it is 9 hours until the bar emerges again to safely walk across. You can learn more about Bar Island here.

After exploring Bar Island, we walked to breakfast at Jordan’s Restaurant. I HIGHLY recommend a Wild Maine Blueberry Muffin! Did you know Maine is famous for its blueberries?!

Once we wrapped up at Jordan’s, we drove over to Acadia National Park and picked up our park passes at the visitor center area. We were SO excited – Acadia has been at the top of my bucket list for so long, and we were finally getting to see it! We made our way to Jordan Pond, and oh, my, gosh. This was a GORGEOUS, easy 3.5-mile trail that looped around the pond, with stunning views in every direction.

Everyone had told us that we needed to go to Jordan Pond House for popovers and tea, which is an Acadia tradition. After the hike, we put our name in – expect there to be a wait! While we waited, we checked out the national park shop and sat on the big hill overlooking the pond. I recommend bringing some cards to play while you wait!

After a long day, we just ordered takeout and spent the evening relaxing in our hotel room. After all – I was almost 25 weeks pregnant and very tired, haha.

Day 5: Acadia National Park, Thurston's Lobster Pound, Bass Harbor Lighthouse

The next day, we woke up and grabbed a quick breakfast at Mount Dessert Bakery. We LOVED this place – they had amazing bagels, breakfast sandwich and pastries.

Next, we went back and explored/did some hiking in Acadia National Park. We did the Gorham Mountain Loop, which was a moderately difficult 3-mile hike with stunning views of the rocky coastline. I highly recommend this hike! At the end of the hike on our way back to the car, we walked around Sand Beach and checked out Thunder Hole.

Once we were done exploring Acadia for the day, we got in the car and drove to Thurston’s Lobster Pound. The CHARM at this lobster shack! We waited in a long line (which you can definitely expect) for the biggest, most delicious lobster rolls and then sat outside overlooking the harbor while eating them. I also recommend picking up a whoopie pie here for dessert, which Maine is also known for! This place was so cool – you could see the lobsters being brought in and steamed in front of you while waiting in line.

After enjoying our lobster rolls outside, we drove over to the Bass Harbor Lighthouse to explore the most famous lighthouse in the Bar Harbor area. There are two paths – I recommend taking the one to the left of the lighthouse to get the better view from the rocks. Definitely wear good, close-toed shoes for this one, as there are some precarious rock scramble situations. The view was beautiful! I wouldn’t expect to spend too much time here – it’s sort of the place you go to snap a picture and then head out (which I found to be different than the other lighthouses we visited in Portland).

When we got back to our hotel, we walked around and explored the Bar Harbor shops and downtown area. Bar Harbor has the most charming downtown ever! While walking around, you NEED to get the blueberry soft serve from CJ’s Big Dipper!

We planned to go to Side Street Café for dinner that night, which was highly recommended to us, but the wait was SO long and we were starving. Instead, we sat outside at an Indian restaurant next door called Royal Indian and enjoyed some tikka masala (if you’re going to go to the other place, definitely arrive early to put your name in!)

Day 6: Acadia National Park, Drive to Kennebunkport

We woke up this morning and wanted to do an easy walk before hitting the road and exploring our next destination. We drove over to hike Jesup Path and Hemlock Path Loop which was just an easy, 1.5-mile loop to stretch our legs and get some fresh air. While you’re here, you can also check out the Wild Gardens of Acadia which are right near the entrance of this path.

We then hopped in the car and headed for our next stop, perhaps my favorite of the trip – Kennebunkport!

Where to Stay in Bar Harbor: We stayed at the Harborside Hotel, Spa and Marina. It was definitely a splurge, but the location was amazing and the grounds are gorgeous.

*I do want to note that one thing we did NOT do on this trip was sunrise at Cadillac Mountain, which many people recommended. If you are hoping to do this, there is a timed entry and you need to reserve tickets ahead of time. They go quickly, so make sure you stay on top of getting tickets here.

Days 6-8: Kennebunkport and Ogunquit

Day 6: Exploring Kennebunkport

We drove from Bar Harbor to Kennebunkport, which is about a 3.5 hour drive. Kennebunk is south of Portland, so you would be making your way back to the Portland area which is perfect if you are going to be flying out of there or Boston at the end of your trip.

When we got to Kennebunkport, we checked into the cutest cottage in the entire world – the Cottages at Cabot Cove. I could not recommend these more. These were the cutest, quaintest little cottages surrounding a small cove. They have small kitchens, a firepit area on the grounds, and access to paddle boats just outside your door. They also dropped off little baskets of breakfast each morning. I mean, you can just take one look at the pictures of the cottages and you’ll be sold!

After we checked in, we went for a long walk to explore downtown Kennebunkport. We grabbed lunch outside on the water at The Boathouse Restaurant and walked all around the boutique shops. Two shops I could not recommend more: Daytrip Society for the cutest selection of curated gifts, and Daytrip Jr. for the best baby store you’ll ever go to in your life. We went back to these two shops several times because I just couldn’t get enough! Downtown Kennebunkport was a dream – I could have walked around forever.

When we were done having lunch and exploring the shops, we walked back to the cottages and sat outside around the fire chatting with the neighbors we met while on our trip.

Day 7: Lobster Tour, Marginal Way in Ogunquit, Lobster Rolls

The next morning we woke up, got ready, and walked to the meeting point for a tour with Rugosa Lobster Tours. We LOVED this tour. It was about an hour and a half tour of the Kennebunk River and its scenic coastline where we got to watch the team haul their lobster traps. We had so many lobster rolls on this trip (get ready to spend a million dollars on lobster rolls alone while you’re here…) that it was fascinating learning all about how they’re caught, and how the lobstermen make a living in Maine. They also recommended some great local spots for the best rolls!

From there, we hopped in the car and drove to Marginal Way in Ogunquit. My parents (separately) grew up going to Ogunquit with their families so I knew I wanted to go there and explore the area for a little. It’s another charming little Maine town. Marginal Way is a scenic coastal walk known for its ocean views and its gorgeous, rocky shoreline – after all the lobster rolls we ate, it was really nice to get some movement in!

We then drove back to Kennebunkport and had another lobster roll at The Clam Shack in downtown Kennebunk. This was by far my favorite lobster roll of the trip. There may be a line when you go, but it’s absolutely worth it!

We headed back to the cottages, attempted to do some paddle boating on the cove, ordered in pizza, and went to sleep. This was our last night here, and we were so thankful for such a wonderful week.

Where to Stay in Kennebunkport: Do yourself a huge favor and stay at the Cottages at Cabot Cove.

Day 8: Check Out

The next morning, we hit the road! We drove the couple hours to Charlie’s hometown since his family was hosting a local baby shower for me, and then we flew out of Providence at the end of the weekend. But if doing this trip, I recommend flying out of Portland or Boston!