Perfect Solo Weekend in Portland, Maine: Wine & Oysters on the Water

I arrived in Portland in the evening and checked into the Portland Harbor Hotel, a beautifully designed boutique hotel in the heart of Old Port. The historic charm of the hotel was perfectly complemented by coastal luxury. The hotel has an on-site restaurant and bar, a gorgeous outdoor terrace, and many seating areas perfect for unwinding with a book, answering a few emails, or just enjoying a quiet moment—perfect for the solo traveler.

Dinner in Old Port

After dropping off my bags, I headed out to explore the cobblestone streets of Old Port. Independent Ice Company, on Wharf Street, was just steps from the hotel and a great pick for a bite to eat.

The dimly lit atmosphere showcased a huge bourbon selection and offered plenty of bar seating, and was very welcoming to the solo traveler. You can try a few bourbon samples or grab a flight, and be sure to order the whipped ricotta!

A leisurely morning

I had a leisurely start to the morning with breakfast delivered to the room, using the hotel credit Fora clients receive. I had nothing specific planned for the day and was excited to let the day unfold.

I started with a walk down Commercial Street, the historic waterfront street in downtown Portland. I walked along the waterfront and stopped in some of the shops along the way.

From there, I continued my walk to the Eastern Promenade Trail, a two-mile trail that connects downtown to the east end. This is a beautiful, harbor-front walk that features sweeping views of Casco Bay. I made my way to the Eastern Promenade, a huge waterfront park, and to East End Beach, where you will find kayaks and paddle boards to rent, food trucks, and beach goers. I walked the beach and watched sailboats come and go from the harbor before heading back downtown.

Insider tip: If you don’t want to walk, there is a trolley tour or bike rentals at the head of the trail in downtown.

Lunch & beers in Old Port

As I made my way back into Old Port, I stopped for a cold beer with the locals at Brickyard Hollow. From there, I wandered down Pearl Street, which is an alley-like side street that leads directly to the waterfront. You’ll find the Harbor Fish Market, a great place to pick up local seafood!

The Sea Bags Factory Store and Maritime Antiques are two other unique stops worth your time.

You’ll find the back entrance to Porthole Restaurant & Pub, a local Northeast diner with an outdoor deck directly on the wharf. It was a great spot to grab a late lunch and listen to live music.

Evening at Eventide Oyster Co.

I spent the rest of the afternoon relaxing at the hotel—reading a book on the terrace, a long shower, and just some down time.

For dinner, I highly recommend Eventide Oyster Co., just a short walk from the hotel. Known for its lobster rolls and raw bar, this was pure heaven and a must for any foodie. Expect a wait, even for a seat at the bar, but it is well worth it. There is a tiny stand-up counter by the raw bar, but I wouldn’t recommend it since it’s such a small place.

The bartenders are knowledgeable and will help you pick your oysters, if you don’t know what you want. This was an excellent way to end the day.

After having coffee in the room while I got ready for my sailing adventure, I stopped at Holy Donut for a famous, gourmet potato donut.

I took my time strolling along the waterfront to the Casco Bay Harbor to check in for the Wine Wise Wine & Oyster Sail.

Wine Wise sail trip

Wine Wise is a locally owned and operated company that offers a variety of wine and sailing events. Erica Archer is the amazing Sommelier who partners with Captain Mary who sails the beautiful 74-foot Tall Ship Frances.

On board, we tasted and learned about five different French wines that were expertly paired with fresh oysters from five different Maine oyster farms. Next to Captain Mary, you could watch the oysters being shucked and loaded onto silver pans that were then delivered to each guest—all while feeling the salty breeze, enjoying the magnificent views of Casco Bay, and making new friends.

It was casual, classy, and truly one of the best food and wine experiences I have ever had.

West End & downtown exploration

After the sail, I walked to the West End neighborhood of Portland, which is known for its grand Victorian architecture and rich history. The Western Promenade is another fantastic park with walking trails overlooking the Fore River. It was the perfect way to spend a leisurely afternoon.

Back downtown, I stopped at Luna Rooftop Bar, located on the sixth floor of the Canopy Portland Waterfront Hotel. With magnificent views, I enjoyed a craft cocktail and an order of truffle fries. This would be a great spot to catch a sunset!

From here, I headed up Exchange Street to browse some more boutique shops and then headed back to the hotel to freshen up and relax before dinner.

Dinner at Street and Co.

For dinner, I stayed close to the hotel and found a cozy spot on Wharf Street. Street and Co. is an upscale, rustic restaurant with a seafood-only menu. You will find some of the freshest, local seafood here. I ordered the appetizer special, which was a grilled octopus, and the scallops in pernod and cream for dinner.

The food scene in Portland is absolutely amazing, and this meal definitely did not disappoint. It was cozy and comfortable at the small, rustic bar and was the perfect end to a great day.

I was up early so that I could catch an Uber to the Portland Head Light and Fort Williams Park—and I’m glad I did! The lighthouse dates back to 1791 and is the oldest one in Maine. The lighthouse itself is situated above a unique rock formation in the harbor that magnifies its beauty.

From here, you can also spot five different lighthouses in Casco Bay and Portland Harbor. It is truly stunning. There is also a small gift shop and museum to explore.

Afternoon exploration

Walking trails throughout the park lead you to Battery Blair (a gun battery that is the largest in its class), Battery Keyes (a small battery located at the fort built in 1906), Goddard Mansion (a true mansion predating the fort), Ship Cove (a small rocky beach big enough to sit and relax or sunbathe), a children’s garden, and several food trucks, including the popular Bite Into Maine known for its fantastic lobster roll.

Yes, this is where I ate lunch, and it was delicious!

Goodbye to Old Port

I left just enough time to walk the cobblestone streets of Old Port one last time before heading home. A trip that centered around a Wine & Oyster Sail turned out to be one of the best solo trips yet.