Maine Day 1 - Portland, Lobster Rolls, and Breweries

Updated: Nov 4, 2020

(Day 2, Day 3, Day 4, Day 5)


Maine had been on our list for a while and with fall upon us, we decided to take the plunge and book a trip to take in the full Maine experience. We booked an Airbnb in the Back Cove neighborhood, which is an eight minute drive to downtown Portland. Our Airbnb host, Dan, reached out prior to our arrival and gave us detailed information about Portland and the surrounding area. Dan has lived in Portland his entire life and has incredible knowledge of the area.


Seventy-two hours prior to traveling to Maine, you must have a negative result from a COVID-19 test. Yelena and I booked test appointments at Rite Aid and completed the test in the drive-thru area. They told us to expect results within two to four days, but we both received our negative results the next day. Armed with Dan’s invaluable advice and our negative results, we were ready to go.


Winking at the bunny hand towel

We flew into Portland early in the afternoon and called an Uber; unfortunately, the expected wait time was 30 minutes. Just as we resigned ourselves to waiting at the airport, our Airbnb host, Dan, gave us a call and offered to pick us up in his convertible. What a guy! Dan arrived in his full glory in about 10 minutes and proceeded to give us a personalized local-perspective tour of Portland. We drove through the downtown area and he pointed out all of the key streets, restaurants, and sights to us.

Photo credit: Dan
Overlooking Casco Bay

After we were squared away in our Airbnb, we called an Uber (which was thankfully much faster this time) and made our way to downtown Portland in search of lobster rolls. We ended up at the Portland Pier and saw Luke’s Lobster. Both Yelena and I ordered lobster rolls and, let me tell you, it was a really good Maine lobster roll! Luke’s Lobster is right on Casco Bay and has great views of the water.

Now, before I go on, let me delineate the two types of lobster rolls - Maine and Connecticut. The Maine lobster roll is served with cold lobster, mayonnaise, and celery on a toasted bun. The Connecticut lobster roll is served with warm meat and melted butter on a toasted bun. They’re both equally delicious!


After taking in way too much lobster meat, we started plotting our next move. Yelena had a friend who lives in the Portland area who suggested we go to the East Bay neighborhood, which has a number of local breweries and distilleries. We met him at Oxbow Blending and Bottling for a few drinks, which were amazing. After catching up for a bit, we wandered next door to Hardshore Distilling, which specializes in distilling gin. Now for a little background: Yelena is not the biggest fan of gin or gin-based cocktails. She ordered a Bee's Knees, Hardshore’s signature cocktail, which combines gin, lemon, and honey. I am not kidding when I tell you that she said this was one of the best cocktails she’s ever had, and the best tasting gin, by far.

After drinks, we went back to the Airbnb for a quick shower and change of clothes before dinner. We made reservations at DiMillo’s On The Water, which is located in a boat on the Casco Bay harbor with scenic views of the water and other boats. I ordered the lobster mac and cheese, Yelena got the Pecan-Encrusted Haddock, and we shared bacon-wrapped scallops and clam chowder. Every dish was amazing, and the service was very efficient.

Once again, after putting way too much lobster into my body, we decided it was time to call it a night. We took an Uber back and promptly passed out.

(To be continued on Day 2…)


Most importantly, don’t forget to see the world, and eat the food.






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