Portland Solo — AKA how many times will I eat lobster?

I’ve been dying to go to Maine ever since I visited Boston a few years ago. Maine is a quick 3 hour drive from where I’m staying in Vermont so when my schedule switched around and I realized I have 3 days off, I hopped in my car for a quick solo trip to Portland.

Masks were worn at all times, except for the occasional photo op.

I’m a pretty laid back traveler and last-minute trips are my JAM. HotelTonight is my BFF. The morning I left, I booked Hilton Garden Inn right on the waterfront for $144 a night for 3 nights. Since I was coming from New York and Vermont, I did not have any travel restrictions in Maine. This hotel was spotless, the staff was very knowledgable about Covid restrictions and friendly.

I mean, let’s just talk about this view from my hotel.

I wasn’t sure where to start my trip, but after walking around Commercial Street, I headed to Portland Head Light, the first lighthouse commissioned in the U.S. I thought that I would park my car, see the light then peace out, but there was so much more to do. There’s food trucks and local vendors set up in the park (you really can get a lobster roll from anywhere) and you can hike the rocks, which I did and then took some time to sit and read and soak up the views. I was going to make it a point to see more of the lighthouses but didn’t get around to it. This was about a 20 minute drive from my hotel in South Portland and the only time I needed my car on the trip.

You don’t go to Portland without eating lobster (or at least seafood) for every meal. I had several amazing meal experiences in Portland but by far the coolest was being able to select my own lobster on the Lucky Catch Cruise and then walking down the street to Portland Lobster Company so they could cook it and pair it with their sides of some corn on the cob, a baked potato and coleslaw. This whole meal was $17. Also, be prepared that this is a messy meal. If I were to go back, I would definitely grab an extra paper plate to discard my lobster shells.

The HIGHLIGHT of my trip was taking a trip on Lucky Catch Cruises lobster boat. For $35 (per person) you take a 90-minute tour of Casco Bay, learn how to catch lobsters hands-on, and see seals. I could not have had better tour guides and captains. They were so friendly and gave great recommendations on things to do, where to go. I could have stayed on the boat all day. If you only have time to do one thing in Portland, this is it.

Shopping lovers, Commercial Street is the place for you. These cobblestone streets host stores with names you’ll know such as Lululemon, but is mostly filled with local boutiques, bookstores and more.

To end my last night, I hopped on Portland Schooner Co‘s sunset cruise. This BYO-food and drink cruise was the perfect end to my long weekend in Portland. The views are unmatched and it was my first time on a sailboat, which lemme be real I don’t think I’ll be on another anytime soon because although I don’t usually get seasick, something about me and this boat didn’t match. It was still gorgeous.

Thanks for the photo, Alina Tyulyu!

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