Local tips, ideas, and locations to curate a dream early summer Maine getaway

There’s something about early summer in Greater Portland that feels exciting. The boats are back in the harbor, patios are open, beach days are possible again, and you can build a whole weekend around good food, lighthouse views, and time on the water. This itinerary is made for a relaxed friend-group getaway, with a mix of Portland, South Portland, Cape Elizabeth, and Yarmouth experiences that are easy to connect over a weekend, but still show off how much variety the Greater Portland region has to offer.

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Day One

Start on the Water with Nauti Sisters Sea Farm

Start the trip in downtown Portland with Nauti Sisters Sea Farm, an oyster farm experience led by owner Alicia. Nauti Sisters is based in Yarmouth, but this year they are offering tours from both Yarmouth and Portland, making it even easier to get out on the water during a Portland weekend. For the Portland tours, Nauti Sisters is partnering with On the Rocks Cocktail Cruises, so you can board right from the Old Port and cruise out through Casco Bay.

The experience is part boat ride, part oyster tasting, and part working waterfront lesson. Along the way, you’ll learn about oyster farming, Casco Bay, Portland’s harbor, and the islands that make this stretch of coast so special. You may pass lighthouses, osprey, working boats, and island views, and if you’re lucky, you might even spot seals.

Once you reach the farm, you’ll taste oysters right where they’re grown. Add in a little sparkling wine and a small group of friends, and it feels like one of the most memorable ways to start a Portland weekend.

Local Tip: The closest parking garage for the boat meeting point is the Casco Bay Ferry Lines garage, but it can fill up quickly in the summer. Give yourself extra time to park before heading to the waterfront.

Check in at The Black Elephant Hostel

After your tour, head to The Black Elephant Hostel, a colorful, funky, design-forward hostel in Portland. It’s located at 33 Hampshire Street, just outside the Old Port, which makes it easy to walk to restaurants, shops, bars, coffee, and the waterfront.

The Black Elephant works especially well for friend groups because it offers both dorm-style and private room options. It’s playful, affordable, and much more memorable than a standard hotel stay.

Cross the bridge for beach time at Willard Beach

From Portland, it’s a quick drive over the bridge to South Portland and Willard Beach. This is one of the easiest beach stops to add to a Portland itinerary because it feels coastal and tucked away without being far from the city.

The beach has views across Casco Bay, with boats coming in and out of Portland Harbor. You can also see nearby islands, forts, and lighthouses from the shoreline. There’s a playground nearby, and in the summer the bathhouse has restrooms, outdoor showers, and a snack bar. It’s a great spot for a low-key walk, a beach blanket break, or a few photos before lunch.

Lunch and Cocktails on the deck at Saltwater Grille

Just down the road, stop for lunch at Saltwater Grille, a waterfront restaurant in South Portland with one of the best views back toward downtown Portland. The restaurant sits right on the harbor, with a large outdoor deck overlooking the water, boats, and skyline.

This is a great place to slow down for seafood, cocktails, mocktails, and a view. The baked stuffed lobster is a showstopper, and the fish tacos are a perfect summer lunch order. Grab a table outside if you can!

Walk around Bug Light Park

After lunch, head to Bug Light Park, also in South Portland. The park has wide-open green space, harbor views, and one of the most charming little lighthouses in Greater Portland.

You can walk right up to the lighthouse, look back across the water toward Portland, and watch boats and ferries move through the harbor. It’s an easy add-on after Willard Beach or Saltwater Grille, and it gives you another quick hit of lighthouse scenery without needing to drive far.

End the day at The Lobster Shack at Two Lights

End the day in Cape Elizabeth at The Lobster Shack at Two Lights, a no-frills seafood spot set right on the rocks near Two Lights State Park. This is not a polished, fancy dinner stop. It’s trays, fried seafood, lobster, picnic tables, crashing waves, and some of the best ocean views around.

Order lobster, fried seafood, fries, or whatever feels right after a full day outside. Save room for something sweet, too. The rhubarb pie is a great way to end the day, and they also have homemade whoopie pies.

The setting is perfection. You’re sitting right above the rocks with miles of open ocean in front of you, waves crashing below, and the kind of view that makes everyone stop talking for a second.

Local tip: Hold on to your fries. The seagulls here are not shy, and they seem to know exactly who just picked up an order of fried seafood.

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Day Two

Start with hot bagels in the Old Port

Start the morning at PopUp Bagels, located right in the heart of Portland’s Old Port at 210 Middle Street.

PopUp Bagels is known for its “Grip, Rip and Dip” approach: grab a warm bagel, rip it apart, and dip it into cream cheese or butter. Their bagels are sold by the bag, and they offer classic schmears along with rotating weekly specials, including both cream cheese and butter flavors.

It’s a great, low-key breakfast stop before a full day outside. The bagels came out warm, the schmears were fun to share, and it was easy to grab everything and go before heading down to the water.

Paddle to Fort Gorges with Portland Paddle

After breakfast, head to Portland Paddle at East End Beach for a guided sea kayak tour to Fort Gorges. Portland Paddle offers rentals, lessons, and guided tours from East End Beach, including a Fort Gorges sea kayak tour that crosses Portland Harbor and includes time to explore the fort.

For anyone who grew up around Portland, kayaking out to Fort Gorges is one of those things you may have looked at your whole life and thought, “I need to do that someday.” This is the way to do it.

The paddle from East End Beach to Fort Gorges took about 30 minutes. We went with a Registered Maine Guide, who gave everyone a safety overview and either a first lesson or a quick refresher before heading out. On the way, we paddled past sailboats, spotted seals, and had beautiful views of the working waterfront and the islands.

The guide kept everyone together and safe, especially while crossing through areas with boat traffic. At one point, he radioed to nearby boats to let them know our group was crossing, which made the whole experience feel safe, thoughtful, and very experienced.

Once we reached Fort Gorges, we mostly had the island to ourselves. We spent time touring the fort, searching for sea glass, getting our feet wet, and taking in the views back toward Portland and out into the bay. You could easily pack a picnic and make this feel like a bigger adventure.

Local Tip: Wear layers and bring a water bottle. It can feel warm on land and much cooler on the water, and conditions can shift quickly in Casco Bay. Portland Paddle also has dry bags available if you need one for your phone, and they have a lock box on land for keys so you don’t have to bring them with you.

A Little History of Fort Gorges

Fort Gorges is the granite fort you can see sitting out in Portland Harbor on Hog Island Ledge. It was built in the Civil War era as part of Portland’s harbor defense system, but by the time it was finished, military technology had already moved on and the fort was never really used the way it was originally intended.

The fort is named for Sir Ferdinando Gorges and was modeled after Fort Sumter in Charleston. It was designed with dozens of gun emplacements and built to help protect the harbor, but today it feels more like a hidden historic landmark in the middle of Casco Bay.

Because you can only get there by water, visiting Fort Gorges still feels like a little adventure. Once you land, you can walk through the old granite structure, take in views of Portland and the surrounding islands, and get a sense of how much history is tucked into the harbor.

Local Tip: Kayaking to Fort Gorges is a huge highlight, but if you’re short on time or want an easier way to get out there, Fogg’s Water Taxi is a great option. They offer water taxi service around Casco Bay and can help get you to Fort Gorges, even though there is no dock.

Refuel at Green Elephant

After kayaking, head to Green Elephant Vegetarian Bistro on Congress Street in Portland.

Green Elephant is an all-vegetarian restaurant that has been part of Portland’s food scene for years, and there’s a reason it has stuck around. The food is consistently delicious, satisfying, and full of flavor, which makes it a perfect post-paddle lunch stop.

The Thai iced tea is always a good call, and the mango sticky rice is a favorite. It’s hard not to order one of their curry dishes, but this is also a good place to branch out and try a few different plates for the table. After a few hours on the water, this was exactly the kind of lunch everyone was ready for.

Spend the Afternoon at Après

After lunch, head to East Bayside for drinks at Après, located at 148 Anderson Street.

Après is especially fun in the summer, with frozen drinks, a large outdoor patio, an outdoor bar, lots of seating, fire pits, food trucks, and playful extras like jello shot buckets. It’s the kind of place where you can settle in for a while without needing much of a plan.

Their frozen drinks are a summer hit, and the patio makes it easy for a friend group to spread out, relax, and spend time outside.

Walk to Belleflower Brewing

From Après, it’s easy to keep exploring East Bayside. The neighborhood is packed with breweries, tasting rooms, and casual spots, so you can build your own low-key afternoon drink crawl without needing to drive between stops.

We stopped at Belleflower Brewing, just down the street. It has a great neighborhood feel, a welcoming patio, and a strong beer lineup, making it an easy add-on after Après.

Local Tip: East Bayside is one of the easiest areas in Portland for brewery hopping. Park once, then walk between spots like Après, Belleflower, Rising Tide, and other nearby tasting rooms.

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A Few more Local Ideas

The Ultimate Maine Weekend Souvenir

For a Portland weekend souvenir you’ll actually wear, we love Liberty Graphics t-shirts. They’re made in Maine, printed on 100% cotton, and feature tons of beautiful nature-inspired designs, from birds and wildflowers to fish, forests, insects, and coastal scenes.

They’re also the kind of shirt that only gets better with age. Liberty Graphics uses water-based inks, and the designs have that classic outdoorsy Maine look without feeling overly touristy. We wore them throughout the weekend, and they were comfortable, easy to style, and perfect for the mix of boating, beach time, paddling, and brewery stops.

You may have also seen Liberty Graphics pop up recently because of the viral vintage Monterey Bay Aquarium sea otter shirt worn by Taylor Swift. The aquarium later brought the design back in partnership with Liberty Graphics, using 100% cotton, PVC-free water-based ink, and plastic-free packaging. The original design was printed decades ago and held up for more than 30 years, which feels like the opposite of fast fashion.

Pick one up before or during your trip, and you’ll have the ideal Portland weekend uniform and a souvenir that actually feels useful once you’re home.

Add a Baycyle Cruise

For another fun friend-group activity on the water, check out Maine BayCycle, Portland’s pedal-powered party boat. It’s a 90-minute cruise with pedal stations, extra seating, music, and views of Portland Harbor.

It’s a great option if you want to be on the water without committing to kayaking, and it works especially well for birthdays, bachelorette weekends, girls’ trips, or any group that wants something social and a little different.

Prefer a Private Boat Day?

For more of a private charter experience, Find Your Way Charters offers custom Casco Bay cruises. Their trips are private and tailored to the group, with views of the bay, islands, lighthouses, and the Portland waterfront. It’s a strong option for a special occasion, girls’ weekend, family trip, or anyone who wants a more curated day on the water.

Oyster Lovers: Add Indigo Oyster Company

Another oyster option to keep on your radar is Indigo Oyster Company, a Maine oyster company that will be launching tours in collaboration with Palmar Collective in September.

You can also find Indigo at the Scarborough Farmers Market from 9:00 am to 1:00 pm on select dates: July 26, August 9, September 13, and October 11. They are also made their debut at Freeport’s Oyster Festival on June 27, where they’ll be shucking oysters.

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Keep Exploring with Visit Portland

This itinerary is just one way to spend an early summer weekend in Greater Portland. Use it as a starting point, then make it your own with more restaurants, waterfront activities, beaches, breweries, shops, and events throughout the region.

Visit Portland has more ideas for where to stay, what to do, where to eat, and how to explore Portland, South Portland, Cape Elizabeth, Casco Bay, and the surrounding communities. Whether you want to add another brewery stop, plan a full day on the water, find more local makers, or build out a longer trip, it’s easy to keep exploring from here.

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