Journey to Portland + Peaks Island

July 15, 2016 § 2 Comments


For my birthday this year, J and I went to Portland, Maine, a random destination I picked because of its relative proximity to the city and northerly location (he’s particularly sensitive to heat, so we didn’t venture south).

So off we went on a Wednesday evening; traffic out of the city wasn’t too bad, and after we were clear of city limits, we pretty much flew along. For dinner we stopped at a random Mexican restaurant near Stamford called Ole Mole and picked up some burritos for the road — they turned out to be very tasty. Good start to the trip.

It was kind of unusual for us to be without a game plan for the night — our hotel reservation in Portland was for Thursday to Sunday — but we figured we’d just stop at a random hotel along the way when J got tired of driving.

Surprisingly, he had enough energy to get us practically to Boston, though by 10 p.m. when I started looking at hotels outside Boston, I slowly realized that every single hotel was full for the night. On a Wednesday! Literally every Hilton, Marriott, IHG and even Holiday Inn Express along the highway was maxed out for the night, unless we wanted to actually stay in downtown Boston (which we didn’t).

Things didn’t get better once we passed Boston — there were barely any hotels between us and Portland, which was still two and a half hours away. It seemed like we’d have to end up spending the night in a barn à la Joseph and Mary.

I started to panic. At this point we were almost at Portsmouth, just an hour and a half away from Portland. There was a random B&B in Portsmouth with a vacancy, but I started calling every hotel in Portland just in case we could actually make it there. J seemed to be in good spirits despite my profound lack of success in finding lodging. “It’ll be great if we could just start our day in town without having to do any more driving,” he reasoned.

I, on the other hand, felt like I was a newspaper reporter again, cold-calling people (and subsequently getting rejected) to try to get a quote for a story. Just like before, all the hotels were fully booked. Welcome to New England tourist season, I guess.

Finally, on my third try, the lady at the Portland Residence Inn told me there was a two-bedroom suite option for $445.

“Ummm…” I looked at J. Didn’t seem worth it..?

Before I could formulate a response, she continued, “I just checked our neighboring hotel, the Press, and they have a king room available for the night for $285.”

I could’ve sworn that I had already called the Press — it was actually my first choice of hotel for our stay, but for whatever reason (they didn’t have any good rooms available idk) we went with the Portland Harbor Hotel instead. I asked her to repeat herself a few times just to be sure I didn’t mishear. But it turned out to be true! It was a miracle!

So we checked into the Press Hotel just before 1 a.m. that night and were very pleased with the room. It was gorgeous and modern and I could see why it was the top-rated hotel in the city. We were so relieved and happy and truly didn’t want to check out the next day. 


In the morning, we had a lovely breakfast in the downstairs restaurant. I was a bit slow getting ready so J went down first and ordered me a “smoothie bowl” and oatmeal. The smoothie bowl was very pretty and clearly healthy, but I think I prefer to drink my smoothies. (We also saw another cafe offering smoothie bowls; are they a thing now, or just in Maine?)

Then we hurriedly packed and bid adieu to the Press to make it over to the Casco Bay port to take a ferry. Our destination for the morning was Peaks Island, just a short boat ride across the water.




We were blessed with flawless weather every day of our trip, and it felt so wonderful to be on the ocean, gawking at the expansive sky and breathing all that fresh air!


After getting to Peaks Island, we walked a few blocks to a bike rental place. We passed by an umbrella cover museum — didn’t go in but I’m sure it was adorable, just like everything else on the island. We also saw a lot of golf cart rentals, which I guess is a good mode of transportation for less mobile visitors, but biking was definitely the way to go.



Their bikes had surprisingly comfy seats! A+

Their bikes had surprisingly comfy seats! A+

Peaks Island is small enough to bike the perimeter in one hour but big enough for people to actually live on (real people, not just vacation homes). There were a couple of small beaches, but most of the shore was pretty rocky. Everything was beautiful, except maybe this mysterious sea vegetation that was everywhere:

Edible or no?

Edible or no?

Pretty purple shell

Pretty purple shell




We even came across this cute (unmanned) honey stand and picked up a bottle to take home. It was surprisingly delicious?! I mean, I’ve had decent honey before and I always appreciated it for what it is, but I’ve never found it that mouthwatering — this stuff was eye-opening. I’ve been adding it to my smoothies and oatmeal every morning.

Every part of our excursion to Peaks Island was perfect, except for the fact that I didn’t realize how much sun we’d get and forgot to put sunscreen on our bodies (I always make sure our faces are covered). J ended up with a pretty bad sunburn and farmer’s tan, oops.






But the water was clear and the air was fresh and we had an awesome time! What a thrill to pedal down the oceanfront road with the sea breeze in my hair!

Maine pt. II: Eat All the Lobster
Maine pt. III: Delightful Finds in Rockland


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