Our first day in Portland, Maine was filled with discovery, art, and a little bit of coastal charm.

We started the morning with a walking tour of Old Portland, diving straight into the city’s rich maritime history and cobblestone character. As we strolled through the Old Port district, our guide shared stories of Portland’s past—of ship captains, merchants, fires, and rebirths. The historic brick buildings, tucked-away alleyways, and harbor views gave us a real sense of the city’s layered past.

The tour wound its way uphill and ended at Fort Allen Park on the Eastern Promenade. The sweeping views of Casco Bay were stunning, even under the gray skies left over from the recent rain. We lingered a bit, watching the boats and ferries glide through the bay, before calling an Uber to take us back to where we had parked earlier in the day.

Next, we made our way to the Portland Museum of Art, one of the city’s cultural gems. The museum’s mix of classic and contemporary pieces made for a relaxing and inspiring afternoon. We especially enjoyed the works by Maine artists—there’s something special about seeing the local landscapes through their eyes.

After the museum, we headed out for dinner. Portland’s food scene didn’t disappoint. We settled into a cozy spot downtown and enjoyed a delicious meal. With full stomachs and happy hearts, we made our way back to our Airbnb to rest and recharge.

It was a perfect first day in Portland—historic streets, ocean views, great art, and even better food. We’re excited to see what tomorrow brings!