Boston, Portland, and Bar Harbor Recap

I just got back from 9 days in Boston and Maine and it might have been one of the most fun family vacations we’ve ever been on. Don’t get me wrong I love, love, love the beach and relaxing vacations, which this one was not, but it was a blast!

We left last Sunday and drove for 8 hours to go up to Boston. We decided that it would be best if we stopped in Boston first because it is a good 10 hours to Portland and 12 to Bar Harbor which is wayyyyy more than we wanted to drive in a day.

Once we got to Boston, we headed up to the North End for some Italian food after checking into our hotel, The Revere. First of all…it’s a gorgeous hotel. We really liked it and would highly recommend it. The beds were especially comfy, which is something pretty much everyone in our family is picky about πŸ™‚

We went to the most adorable little restaurant up in the North End and the food was soooooo delicious! I had a chicken and broccoli penne with a cream sauce. Oh and the restaurant was called Al Dente.

Boston, North End

The next day we went on a quick tour of the City of Boston. It was a blast to learn all about the history of the town. We definitely got our fill of fun knowledge and cool photos πŸ™‚

I think the funniest thing was the donkey representing the democratic party in front of the old town center and then two footprints with elephants Β in them which said stand in opposition to demonstrate the republican party. I thought it was clever!

After the walking tour (we had the nicest tour guide by the way) we packed up all of our stuff and headed out to Portland. It was just a few hours to get there, but we stopped in Ogunquit, Maine for lunch first!

Ogunquit is literally the cutest and smallest town I have ever seen! I loved it πŸ™‚

We ate at the Lobster Shack, which I believe was recommended to us by one of my mom’s friend. Whoever recommended it was absolutely correct…it is a great place to stop for lunch and they have great lobster rolls!

I don’t necessarily love cold lobster (or should I say, I learned that I don’t love it) but everyone in my family had great things to say. It was my brother and I’s first time trying lobster!

I highly recommend trying a Connecticut style lobster roll, which is made without mayonnaise if you’re anything like me and can’t stand the stuff! But if you’re like my dad or my brother…the traditional style is perfect for you! This place also had some of the best clam chowder I have ever had in my life…perfectly creamy and filled with huge chunks of clam πŸ™‚

After trying out the food at the Lobster Shack we took a little self guided tour around the teeny tiny town…they have a draw bridge that they let anyone, aka random people, open and close when big boats come into the harbor…how can they do that?! It was so cool!


After leaving Ogunquit, we made our way to Portland, which is such a cool place! There were tons of restaurants there and cute little shops and even a floating restaurant! We didn’t eat at the floating restaurant, but we did go on a really fun sunset boat tour of the place!


The cruise was a blast! I learned so much about the history of the area and saw some seals! Seals are just so cute looking πŸ™‚ I loved getting to take some photos out on the water too.

After the cruise, we went to a BBQ place…I forget what it was called but it wasn’t the greatest, so it is probably best left unnamed. I think I’ll leave BBQ to the southerners πŸ˜›

The next day we went to Peak’s Island to do some kayaking. The last time I went kayaking was when I was 8 years old in Alaska and the kayak that my mom and I were sharing had a broken rudder, so needless to say I was a little nervous about getting in a kayak in the ocean πŸ˜›

It went super duper well and was so much fun! I had a blast and it was definitely a great workout πŸ™‚ Peak’s Island was great too…It’s the most populated island in Portland and it has one of everything…one grocery store, one ice cream place, one police officer…you get the idea πŸ™‚ Their motto is “if we don’t have it, you probably don’t need it.” I think that’s probably true!


This lighthouse, the Portland headlight, is the most photographed lighthouse in Maine πŸ™‚Β DSC_0338DSC_0358DSC_0398

From Portland, we headed to Bar Harbor. Bar Harbor might be the most beautiful place I’ve ever seen and I’m usually 250% partial to the sandy beaches of Topsail Island (which by the way was on HGTV on Sunday night in an episode of bargain beach house hunters or something like that which was both cool and sad all at once because we like to keep the island a secret :P).

Anyways….Gorgeous…and great great great hiking in Acadia National Park. Did you know they have over 2 million visitors every summer?! That’s nuts! We stayed in a cute AirBnB right in heart of town, which was perfect.

We did stop on our way out of Portland to grab some donuts at the Holy Donut. I had read about it as a must-go place in pretty much every travel article about Portland, so I convinced everyone that we needed the donuts. Not that that was very difficult to do πŸ˜›

They had pretty much every flavor of donut imaginable…we went in expecting to get 4, but came out with a dozen. We got some that were blueberry, some dark chocolate coconut, a lemon one, a maple bacon one, some berry flavored one, an original one and even a cannoli one!!

We were within walking distance of some of the best restaurants I have ever eaten at! The first night we were there we ate at the Side Street Cafe. They had great reviews on Yelp and TripAdvisor and they definitely lived up to expectations! I had a caesar salad and lobster mac and cheese.

The lobster mac and cheese is supposedly Paula Dean’s favorite meal at the restaurant, so naturally I had to have it since I love Paula Dean πŸ˜›

It was absolutely the most delicious mac and cheese I’ve ever had!

best Lobster mac

We also had a FANTASTIC blueberry pie! Just the crust alone was to die for, but the sweet blueberries in combination with the slightly sweet crust and vanilla bean ice cream was absolute perfection…

However I have a less than stellar photo to show you all the pie…you’ll have to take my word for it. We did go back to the restaurant again strictly because the pie was so good, if that means anything πŸ™‚

Our first full day in Bar Harbor consisted of some hiking in Acadia National Park at Jordan’s Pond and Bubble Rock hikes. They were so much fun! I love hiking and have gone to a bunch of different places this summer, but this was easily the best! So so so scenic…I could have taken a thousand photos and never once gotten bored!

Jordans pondbubble hill

I loved how much time we got to spend outdoors πŸ™‚ The next day we went on a whale watching tour, which was a blast! I usually get kind of sea sick, but my dad grabbed me some Dramamine to help stave off some of the sickness. It definitely worked and I was able to use my telephoto lens for the first time in forever!

We got to see a couple of humpback whales, Spoon and Sword, for quite some time! They were breaching and playing around so much! It was almost like they were showing off for our tour.


We also got up one morning for sunrise! We had to get up by 4am to drive and get a parking spot at Cadillac Mountain, but we did get the satisfaction of saying we were one of the first people on the east coast to see the sunrise. It was pretty beautiful πŸ™‚


The best part about getting up that early is that you beat all the lines to breakfast πŸ˜› Kyle is a master of finding good places to eat, so we ended up at a place called The Two Cats Cafe and Inn. We thought he may have just picked it because he likes cats so much, but he definitely picked a winner! They had great coffee and even better biscuits with strawberry butter! Not to mention delicious spicy hash browns and scrambled eggs πŸ™‚

2 cats cafebreakfast 2 cats

It was easily one of the best breakfasts I’ve had in a long time…I wish I could make breakfast like that for myself every single morning πŸ™‚

I really loved all of Bar Harbor and everything there…I would go back in a heartbeat!

After leaving Bar Harbor, which is a place that I could easily spend a whole week or even two, we went back to Boston to catch a Red Sox game. I’ve never been to a game like that before! As Kyle put it, it isn’t as “Family Friendly” as National’s Park…it’s just way more lively and people seem to be way more into the game!

One guy walked past us wearing all Met’s stuff and several people booed him πŸ˜› There were also a ton of home runs during the game, which was sooooo much fun to watch!

Fenway Park

After the game, we went across the street to a brewery called BrewWorks for some pretty good beer! I don’t usually love beer, but it has been growing on me. I had one called a Watermelon Ale!

Watermelon beer at BrewWorks

So yummy! Afterwards we went somewhere in Chinatown for dinner…it was called Q and it was delicious! They’re known for something called hot pots, but I got chicken chow mien and ate some of my mom’s sesame chicken πŸ™‚ I’d highly recommend it if you’re in Boston and in the mood for Chinese!

Overall it was one of the longest and most fun vacation’s that my family has taken together. I’d love to go back to Maine someday and do more hiking up there. There are also a whole bunch of small towns that we drove through on Coastal Route One that I would like to visit! Hopefully soon I can go back with some friends πŸ™‚

Have you ever been to Boston or Maine?


What’s your favorite place to vacation?

  • usually it’s Topsail or a beach, but Maine/ the Northeast is now definitely a contender!

3 thoughts on “Boston, Portland, and Bar Harbor Recap

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