Last summer we took off on an East Coast Tour from Bar Harbor to Boston and boy do I have so much to tell you because this trip needs to be on your bucket list. But brace yourself. Travel is my love language and I do NOT play around when planning a trip. I research ALL the things. I start 12 – 18 months in advance. I leave no stone unturned.
When we decided to take this trip I knew I wanted to pack a lot into the 9 days we had. And I did just that. If you are planning to take your own East Coast Tour from Bar Harbor to Boston (or in reverse!), this itinerary will help you hit all the charming, can’t-miss spots along the way – perfect for creating unforgettable memories with your favorite people. I am going to tell you everything I learned, experienced, and have an opinion on. I’m real good at that last one by the way….
Day to Day, Play by Play
I am going to break this trip down for you exactly as we took it because that’s how my brain works best and I think you’ll find it incredibly helpful if your brain works like mine. If it doesn’t, no worries. I am about to give you so much info, there’s no way you’ll walk away empty handed! My husband and two daughters all say this is their favorite family trip that we’ve taken and I have to agree. Being from Tennessee, we were in awe of the rocky coastlines and fabulous weather.
Speaking of weather, we were there in June and it was beautiful! Some chilly nights, some sunny days, a little bit of rain, and a whole lot of crisp, refreshing air. Packing was our biggest challenge because we had to pack both summer and fall clothing so there may have been a little bit of overpacking that occurred. I’ll just say this…we should have rented a bigger vehicle. Lesson learned.
Day 1 – Bar Harbor
We flew into Bangor Maine – smallest airport ever. Like ever. Also the smallest ever? Our rental car. Oops. Or maybe it was the size of all of our suitcases that made it look so small. Whatever the case, we were packed in like sardines and an upgrade wasn’t available so don’t be like me. Size up. Especially if you have to pack for two seasons. And especially if your hubby is big and tall like mine and appreciates leg room and headspace.
We had to make a quick stop by Stephen King’s house for a photo op since he lives less than 5 minutes from the airport. It was pretty neat to see and I am glad we stopped for a photo but rumor on the street is that he doesn’t even live there anymore. I was hoping to catch him mowing the yard or checking the mailbox. Boo. Haha…see what I did there?!
We had to make the drive from the airport in Bangor to Bar Harbor. We made it in about an hour and a half. It was a super easy drive. Nothing scenic or noteworthy but I really enjoyed looking at all the houses and buildings along the way. It’s very different than what you see in Middle Tennessee.
Once we made it into Bar Harbor, we checked into the Bar Harbor Grand Hotel – 
‘s!
Let me just tell you…absolutely spectacular. I highly recommend this hotel if you find yourself in Bar Harbor. It’s hands down the cleanest hotel I’ve ever stayed in, the room is huge, and the free breakfast is excellent! Plus, it’s right on Main Street and a quick, easy walk to everything downtown Bar Harbor. They have the cutest little front porch you can sit on and watch the world go by. It’s so peaceful and relaxing. I sipped coffee on that porch and wished I could stay forever. It just feels good.
I mentioned the free breakfast – it’s the very best breakfast I have ever had at a hotel. You cannot go wrong if you choose this adorable little hotel. I almost always book through Booking.com because I can find amazing deals. This was no exception. The cost was very affordable for the area and the perks I mentioned made it even more worth it.
We had lunch at the Thirsty Whale – it’s a fan favorite around in Bar Harbor but it did not hit the spot for me. Everything was fried and I am a grilled seafood kind of girl. Lots of clams up in them parts. Lots. They are worth a try, but I prefer the lobster. More (lots more) on that later. We had some time before the sun went down so we walked over towards Bar Island at low tide – you can only get there during low tide when the water is down. You’re basically walking on the ocean floor which is pretty neat.
We walked around the harbor and checked out all the boats before we finished off the night with some ice cream at Ben and Bill’s Chocolate Emporium. Travel days zap us so we crashed pretty early to rest up for Day 2!
Day 2 – Acadia National Park
We had breakfast at the hotel before we headed to the park. Delicious! And fun little fact – they serve baked beans for breakfast around there. I’m the only one who ate some 
You cannot go on an East Coast Tour without hitting up Acadia National Park. It’s the ultimate journey along the seaside and it is a stunner! Once we arrived in Acadia National Park, we walked the Ocean Path (gorgeous!), made sure we hit up Sand Beach, enjoyed the views from Otter Cliff and stopped by to see Thunder Hole before heading out to lunch. I stopped often to just gawk and stare. I have dreamed of this trip since I was a little girl who got lost in books and was enamored by the stories set high up on the cliffs above the ocean. I just kept closing my eyes and thanking God for the gift of being able to see it with my own eyes. It’s hard to put into words how it feels out there on those cliffs. It’s just so peaceful and majestic.
For lunch we took a ride out to Beals Lobster Pier because there were raving reviews all over Yelp and I am an avid Yelper. It was Taylor’s first time ever eating lobster. She’s a fan! Chad had his first of like 12 lobster rolls for the trip. I. am. not. kidding. Twelve. The man ate twelve lobster rolls in 9 days. TWELVE.
We had a sunset reservation for Cadillac Mountain so after a long nap and some front porch sitting at the hotel we headed back into the park to experience that view. The pictures do NOT do it justice! Whatever you do, do not skip this! You can also do a sunrise reservation but they are tough to get! You have to be logged in right at 10 am (EST) 90 days in advance of the reservation date you want OR you can log in 2 days in advance of the reservation date. 30% of the reservations are given out 90 days in advance, 70% are given out 2 days in advance. Good Luck!
We stopped by Ivy Manor Inn to cap the night off by the fire. That little Inn is absolutely adorable and I could have sat there all night long. All that ivy growing on the side? With a fire and live music, red adirondacks to hang out in, and a bartender mixing drinks. Perfection really.
Day 3 – Bar Harbor/Frenchman’s Bay/Acadia National Park
We woke up to a very rainy day but we chose to make our own sunshine. Sometimes you just gotta roll with it.
Blueberry Yogurt Parfait for breakfast at the hotel – a must while in Maine since blueberries are the state fruit. They are in everything there! Even the cornbread 
You cannot go on an East Coast Tour and not get out on the water so we started off the day with a lobster boat tour by Lulu’s Lobster Tours. We had a fabulous guide who did an amazing job of sharing all about lobstering, seals, and the history of Frenchman’s Bay. The entire family loved the experience and Tay even got to band one of the lobsters. Taylor and I also saw some type of whale surface 3 times but I wasn’t able to catch it on video. I highly recommend this tour if you visit Bar Harbor! Yes it is touristy. You’re a tourist! And as far as “touristy things” go, this is the bees knees.
After our tour, we were hungry so we walked over to Side Street Cafe where I had a cup of Lobster Stew. It was fantastic and I could have eaten a gallon of it. We all enjoyed our meals at Side Street and I would give it 4 ‘s stars overall. The Lobster Stew however……it gets 5 ’s all by itself. Delicious. It was one of my favorite meals the entire trip.
Our next stop was Bass Harbor Lighthouse. I would’ve loved to have gotten better pics of this for you but you have to navigate a very rocky coastline to get a great vantage point and with that days rain, some of those rocks were pretty slick. I decided it wasn’t worth risking a broken appendage just to capture the perfect pic so feel free to google it if you want to see how truly picturesque it is
Our final stop today was the Wonderland Trail at low tide. We were hoping to see cute little starfish and such but no luck. We did see some unique looking seaweed, some dead crabs, pretty rocks, a few shells, and even a giant jelly fish.
It steadily rained most of the day which was kind of a bummer but when those rain drops hit the spruce trees during our hikes, the smell was so refreshing. There’s just something magical about coastal air mixing with mountain air while the waves crash into the rocks. I may have to buy myself a cliff house instead of a beach house when I win that lottery I don’t play.
Day 4 – Travel Day to Portland & Busted Plans
Day 4 was a scheduled travel day to Portland with pit stops in Camden, Wiscasset, & Boothbay Harbor. Busted. What is it that saying about “the best laid plans often go awry?” The weather completely obliterated my highly organized & well thought out itinerary for Day 4 and if you know me, you know I did not take that well. Planner love problems.
We woke up to a forecast of a Level 3 out of 5 severe storm threat in our entire travel path today. Possible tornadoes, dangerously high winds, and flooding. The news said they haven’t had one of these type of alerts in years. Guess we took a little Tennessee to the coast with us. Since we couldn’t stop at all the scenic locations we had planned on, we just drove 3 straight hours in the pouring rain to Freeport, Maine where we hit up the LL Bean Flagship store. It’s massive and a tad overwhelming. Not gonna lie. I shut down a little bit.
We made it to Portland a little after 4 pm, checked into our hotel super quick, and set out to explore the Old Port area of Portland and the Harbor before the next round of rain came in. Chad needed more lobster so we ended up at Luke’s Lobster on the pier. Our waterfront dining experience was more like dining inside of a cloud. The fog was thick enough to cut with a knife.
The Old Port area of Portland was pretty neat and I’m glad we got to see it but I could’ve done this part of the trip in a few hours and been on my merry way. No overnight stay needed. The cobblestone streets and old buildings were fabulous. I wish we could have spent more time just hanging out there in the Old Port area but we ran out of daylight and sunshine.
Day 5 – Portland and Kennenbunkport
We woke up on Day 5 to beautiful sunshine. Thank you Lord! I was so grateful! We packed up and headed straight to the Holy Donut to try the famous Maine potato donuts that are all the rage here. I tried Sea Salt Chocolate and enjoyed it – not too sweet and had a great texture!
As we headed south on our East Coast Tour, we drove into Cape Elizabeth to see the Portland Head Light and I LOVED it! It was definitely one of my top favorite stops on this trip. I loved the coastline surrounding the lighthouse and the waves crashing into the rocks. I also just went ahead & picked out a few houses on the coast there that will work just fine for my summer home after retirement.
After the lighthouse, we headed to our next stop in Kennenbunkport – that place is ADORABLE. We stayed in a super cute little airbnb right in the heart of Dock Square that was built in 1860. It’s charming and the owner is a total sweetheart. I booked it through Booking.com. I would definitely stay there again. So centrally located and homey!
We stopped by St. Ann’s Episcopal Church (beautiful) and took the scenic drive along Ocean Avenue (any of those houses will work just fine for retirement too…), all the way up to Walkers Point to see the Bush Family compound (gorgeous).
Next, we decided to do some shopping around Dock Square and had lunch at Alisson’s – yet another lobster roll for Chad and another cup of Lobster Bisque for me. We may start to grow claws at anytime now.
We ended the day hanging out in the house and I decided to cook one of our favorite dinners so we could stay home to rest and watch our Vols play Game 3 of the College World Series. They won. We knew they would. Go Vols!
Day 6 – Ogunquit
We woke up the morning of Day 6 and drove about 25 minutes into Ogunquit to check out the town & the beach there since it’s been voted over and over again as one of the best in the U.S. The first thing we did was walk the Marginal Way and it was fabulous! I could’ve spent all day out there but I didn’t because….it was 86,400 degrees there when it was only supposed to be about 73 degrees at that time of year. They were experiencing a very abnormal “heat wave” and the sun beating off the concrete of Marginal Way was rough!
But. the. views. Good grief. And some of the houses along Shore Road in Ogunquit are even more stunning than the ones in Kennenbunkport. I need to know what all these people do for a living….
We stopped by the Cliff House in Ogunquit just to check it out because Chad and I have it on our bucket list for a future anniversary trip. It was breathtaking so we may have to bump that up on our agenda. We are going to be celebrating our 20th Anniversary in 2025. Seems like as good a time as any to make that happen! East Coast Tour Round 2 coming right up. Stay tuned…
Next we stopped at Ogunquit Beach to stick our toes in the sand. Y’all’. That is the coldest water I’ve ever felt. It felt weird to feel the sand between your toes while worrying about the possible need for amputation due to hypothermia at the same time. I have no idea how the people at the beach were up to their chests. I would’ve coded.
Chad needed yet another lobster roll so we had dinner at Mabel’s Lobster Claw in Kennenbukport. He said this was his least favorite lobster roll yet but my Steamed Mussels were so tasty! I ate the entire platter. No regrets. The blueberry pie? Meh. To be known for their blueberries, I expected way more. Maybe they need a southern gal to show them how it should be done? I’ll just buy a house up the street and open up my own shop. Not kidding.
Day 7 – Salem & Boston
We checked out of our Kennenbunkport house first thing in the morning and headed south to spend the day in Salem!
Salem – that was not what I was expecting. I was completely surprised to learn that Salem is not a small, compact little village type town. I’m glad we made the stop and I enjoyed seeing some of the sites but I must admit that I was a tad underwhelmed. I did enjoy seeing all the buildings from Hocus Pocus because it’s one of my favorite movies ever. And I realized that I have failed my husband by never making (forcing) him watch it with us. All day he kept asking “now who is Max?” “Who lived here? Allison? Who’s that?” “Who is Thackery Binx?”
We made it to Boston early enough to explore so we booked a Duck Tour so the girls could see the city and many of the notable landmarks. Taylor even got to drive the Duck Boat for a few feet. We had a fabulous tour guide who goes by the name “Hot Wheelz”. I recommend requesting him if you’re planning to book a Duck Tour of your own.
It started raining the last 5 minutes of our tour so once we got off the bus, we went into the Prudential Center for a little shopping while we waited for the rain to pass. We left to walk back to the hotel which was about 1 mile away. Barely sprinkling. Perfect.
200 feet down the road….the sky opened up and we had no choice but to hoof it back in the pouring rain. We looked like drowned rats when we got back. All of our tennis shoes and clothes were completely soaked through and our hotel didn’t have laundry facilities. Good times.
Day 8 – Boston
You need to know this… I LOVE Boston. That place has my heart. I had to reign in my commentary for Day 8. I could share about Boston for hours. And hours.
We started off Day 8 with a stroll through Boston Commons. I love that park so much. It’s beautiful and clean. I made sure we cut through it several times today as we criss-crossed all over town.
Make Way for Ducklings statue – we had to get a photo op with this statue. When Chad and I visited Boston in 2013, the souvenir we took home to Courtlyn was a copy of the book that inspired the statue and a stuffed duckling. She loved it and has never forgotten it so this was a must do for her!
Next up was Beacon Hill & Acorn Street – this area is my absolute favorite area in Boston. The bricks, the cobblestones, the row houses, the gas-lit street lamps, the alleys, the old leaded windows…. it’s a definite must see if you come to Boston! If I ever find myself with an abundance of cash flow, a home in this area will be a must. It’s just so dang dreamy.
The Massachusetts State House – serves as the home for the State Senate, House of Representatives, and Governor’s Office. It’s dome is gilded in 23-karat gold leaf. The girls weren’t very interested in that little slice of history but I made them read about it and take a pic anyway. Vacation needs some education sprinkled in here and there so my children end up well rounded and cultured.
The Holocaust Memorial – we paused to walk through the Holocaust Memorial to remember all of those who lost their life in one of the darkest chapters in history. This is another must do stop on your tour of Boston.
We were getting hangry so we decided to swing by Quincy Market & Faneuil Hall – we hit up the market for lunch (and yes for all those wondering, Chad had ANOTHER lobster roll) while the girls and I shared some Chinese food because we needed a seafood break
We had to stop at the Build A Bear in Faneuil Hall so Courtlyn could get her Red Sox Souvenir Bear, Mookie. He’s coming home with us to keep Jeter company who came home with us from New York last year. Her obsession with Build A Bear is next level and she has turned it into a souvenir must do everywhere we go.
THE NORTH END: It deserves it’s only little section. Another dreamy area of Boston in my opinion.
Mike’s Pastry – you can’t come to Boston without going to Mikes in the North End! Chad got a regular cannoli, I got a Florentine cannoli (it’s the best!), Taylor got a raspberry turnover & Court tried the famous Boston dessert, Boston Crème Pie. It was all delicious!
Sacred Heart Italian Church – gorgeous old church with 2 different sanctuaries. One upstairs and one downstairs and they have services in both.
Paul Revere House – we got free tickets for the Paul Revere House from our hotel so we went through and toured it. It was built around 1680, and is the oldest remaining structure in downtown Boston. It was neat to walk through and imagine what it must have been like to live there. And hard to believe I was standing in a home that’s almost 350 years old.
Granary Burying Grounds – this cemetary is the resting place of many famous Patriots, including Paul Revere, John Hancock and Samuel Adams. We loved reading some of the old tombstones.
Cheers – we had to stop and grab a photo op at the famous bar that inspired one of the best sitcoms ever. It made me want to come home and binge watch some “classic TV”
Boston Sail Loft – we chose this location for dinner because it had fabulous reviews and recommendations by locals. Meh. I give it 2 . Chad got….you guessed it! ANOTHER Lobster Roll! 
After Dinner – 2nd Mike’s Pastry trip! The girls wanted to go back for cannolis of their own since they didn’t get them the first time. Nutella for Court and Florentine for Taylor (because like I said…it’s the best flavor!)
Day 9 – Boston & Fenway Park
Day 9 was our final stop on this East Coast Tour and it was all about the Red Sox and Fenway Park. It was a definite trip highlight.
Chad & I toured Fenway back in 2013 so we knew it was an experience that we wanted our girls to have on this trip. They were not disappointed! We got to hang out on the Green Monster, tour the Press Box, and try out some of the best seats in the house. We learned that Fenway has its own rooftop garden & they use the crops grown there in the healthy options concession stands. Whatever they don’t use they donate to food banks. Love it.
After the tour, we grabbed a quick lunch in Eataly at the Prudential Center then we went back to the room to rest up a little bit before we headed back to Fenway for that night’s game against the Padres. We had excellent seats along the first base line and even though we didn’t pull out a win, we still had the best time experiencing Fenway with our girls. Perfect weather, a few Fenway Franks, and a little Sweet Caroline with 32,000 strangers. We all agreed it was the best way to wrap up our East Coast Tour
I think it’s easy to see that this vacation was one for the books. My entire family says it has been their favorite trip so far. And we have taken some pretty fabulous vacations. There was just something different about this one.
From the rugged cliffs of Acadia to the charming cobblestone streets of Boston, this East Coast adventure was everything our travel-loving hearts could’ve hoped for – and more. Each stop brought its own kind of magic, from the coastal beauty of Bar Harbor to the storybook charm of Kennebunkport, the rich history of Salem, and the harbor town haven that is Portland.
Whether you’re planning a romantic getaway, a family vacation, or just dreaming up your next adventure, my entire family can’t recommend this trip enough. The East Coast has officially stolen our hearts – and something tells us it might steal yours too.
Pack your bags, bring your appetite, and get ready to fall in love with the beauty, history, and salty sea air of the Northeast. You won’t regret it.
