Charming Portland, Maine – the suite life of travel

Approaching the historic city of Portland, I arrived from the south crossing Casco Bay Bridge. By way of 1A, I reached DiMillo’s on the Water for lunch. I was excited for fresh seafood and a waterfront view.

I ordered the Jumbo Shrimp and Wedge Salad as starters. There were so many amazing options on the menu, so I chose the Lobster Roll sandwich with a side of cole slaw. Absolutely amazing!

Tony DiMillo first opened his restaurant, Anthony’s in 1954 because of his love for seafood. Located on Fore Street in Old Port, Tony’s business flourished, bringing in business from both locals and visitors alike. Anthony’s continued to grow, moving to Center Street, and by the late 70’s, he purchased and reinvented the Long Wharf transforming it into “DiMillo’s Marina”. With 120 slips, boaters had the opportunity to dock and enjoy a fresh seafood meal with a spectacular view. The current restaurant opened in 1982 as “DiMillo’s Floating Restaurant” as the only one of its kind along the Upper East Coast, accommodating over 600 guests. DiMillo’s legacy lives on as his family continues to create an exceptional dining experience with incredible views of Portland’s Harbor.

Although I could have stayed here all afternoon looking out into the bay, I had planned to walk off my lunch and explore the Old Port. With its cobblestone streets, I found myself lost in time visiting the specialty shops and boutiques.

My curiosity brought me to the holy donut to try a Maine-style donut. Founded in 2010, Leigh Kellis uses a northern Maine recipe to create her amazing donuts. Her special ingredient is riced potatoes which provide “added flavor, texture and consistency” to her 24 different flavors of donuts, including gluten-free selections. I couldn’t resist ordering the Dark Chocolate Sea Salt and Maple Bacon flavors which were incredibly moist and absolutely delicious.

I was completely mistaken when I thought the Thirsty Pig was just another craft brewery and excited at the endless possibilities of pairing specialty hot dogs with local beers. From the BBQ Bahn Mi to the Viking, there is not a combination they haven’t created.

Luxurious yachts docked along the waterways are registered from multiple states along the east coast. What a wonderful way to spend the afternoon than to tie up in Portland and explore the interesting port.

I would have never guessed that Portland was a cruise ship stop and it was such a wonderful surprise to see the Grandeur of the Seas docked in town for the day.

Approaching the end of my walk, I came upon an amazing artistic installation designed by Andy Rosen, a South Portland artist. Titled, “Unpack”, the display was created from fake fur, PVC pipe, foam, and aluminum piping. According to Rosen’s website, “The work imagines a pack of once domesticated dogs turned wild and abandoned on a pier waiting for their “masters” to return.”

And so, it was time for me to make my return back to Boston to prepare for a morning of meetings. I was happy that I took the time to visit the beautiful, artistic port town of Portland to explore its lighthouses, enjoy its deliciously fresh seafood and to experience its charm.

Have you visited Portland, Maine? I would love to hear about your visit and the things that you experienced here if you would kindly leave a message in the comments section below. Many thanks for reading about my visit to Portland and wishing you many Happy Travels!

What to See and What to Do:

The Holy Donut
177 Commercial Street
Portland, ME 04101
Telephone: 207 331 5655

The Thirsty Pig
37 Exchange Street
Portland, ME 04101
Telephone: 207 773 2469

Where to Stay:

Inn at St. John Portland In-Town
939 Congress Street
Portland, ME 04102
Telephone: 800 636 9127

Where to Eat:

DiMillos
25 Long Wharf
Portland, ME 04101
Telephone: 207 772 2216

What to Eat:

Seafood, especially lobster!

What to Read: