8 a.m. Breakfast in a colorful spot
Ugly Duckling, which opened in 2023 with a big U-shaped counter and a come-as-you-are vibe, is the latest project by Ilma Lopez and Damian Sansonetti, owners of the nearby Spanish-French brasserie Chaval. Breakfast sandwiches come on housemade English muffins. The No. 2, which includes two fried eggs, house pork sausage, American cheese and ketchup, is a popular order ($11.75). You might need a fork to finish the Como Se Dice Buongiorno ($12.75): fried egg, hash brown, prosciutto, jalapeño, arugula and garlic aioli on an English muffin with everything-bagel seasoning.
10:15 a.m. Ride the ferry
Catch the 10:15 a.m. boat to Peaks Island at the Casco Bay Lines ferry terminal on Commercial Street. The island, with nearly 1,000 year-round residents, was once home to an amusement park and now has a no-shoes-required vibe. Part of the city of Portland, it sits just three miles offshore but feels much farther. During the 17-minute trip (from April to October: $14 roundtrip for adults, $7 for seniors and children), take in a view of Portland from the water, watch for harbor seals and pass by Fort Gorges, a formidable granite military fort built in the mid-19th century and now a frequent host to kayak tours and history buffs.
10:45 a.m. Explore Peaks on two wheels, then grab a pie
You can explore the island by foot, but a bike is handy to make the nearly four-mile loop around the perimeter. Bring your own on the ferry for an extra fee ($7 adult, $3.50 children), or rent one from Brad & Wyatt’s Island Bike Rental ($20 for two hours, $30 for four hours — rentals are first-come, first-served, no website). You’ll find great spots for exploring the rocks on the east side of the island, with views of the Atlantic Ocean. Before catching the return ferry, circle back to Il Leone for salad and pizza cooked in a wood-fired oven and eaten at a shady picnic table. The menu typically includes at least one pie that follows the harvest, highlighting Maine-grown garlic scapes, heirloom tomatoes or squash blossoms (pizzas start at $17.95).
4 p.m. Hunt for treasure
Think of an indoor flea market and you might imagine rows of booths, some full of beauty, others full of dust. Back on the mainland, Open House instead arranges furniture in cozy living-room vignettes throughout its 10,000-square-foot shop on Congress Street, which has a large selection of vintage clothing and handcrafted goods. Items range in price from $5 for packable trinkets to a few thousand dollars for midcentury-modern antiques. And the owners welcome browsers — no stuffy gatekeepers here.
5 p.m. Find a good book
Maine has a rich literary past and present — for starters, Stephen King and Lois Lowry live and write in the state. In Portland, used, independent and specialty bookstores abound. Linger in the beautiful children’s section at Back Cove Books, in the Woodfords Corner neighborhood, which displays its biographies and current affairs books in an old bank vault. Or visit Print: A Bookstore, with its expertly curated staff picks and a large section highlighting Maine writers. Both shops draw an impressive slate of author readings and other events each month, so check their calendars online.
6:30 p.m. Eat from the sea
Plenty of restaurants in Portland serve lobster, but few get you as close to the lobster boat as Luke’s Lobster, a lobster-shack chain that has a full-service restaurant on the end of Portland Pier, off Commercial Street. The two-story restaurant, with a view of the Fore River as it meets Casco Bay, sits next to the company’s commercial lobster-buying facility, where lobster boats dock to sell their catch, some of which goes directly to the kitchen. (No reservations during the peak summer season.) Or reserve a table at Bar Futo in the Old Port to try skewers of squid, fish, pork belly or chicken ($7 to $9 each) grilled over binchotan, or Japanese charcoal, alongside a perfectly carbonated whiskey highball made with a Suntory Toki machine ($14).
8 p.m. Listen to the local sound
Portland’s go-to venue for summer concerts by nationally touring artists is Thompson’s Point, an outdoor stage near the bank of the Fore River. Included in the 2024 lineup are Goose, Counting Crows and Dark Star Orchestra. But One Longfellow Square, in the West End with 180 seats, has a cozy feel that lends itself well to the folk and roots music that makes up most of its shows. Ticket prices vary but start around $20. Just half a block away is Blue Portland Maine, which hosts jazz and more. Half the shows are ticketed, with prices between $10 and $20, and half are free with a hat passed for the artists.
