While we’re fierce advocates of Portland’s Old Port (the late night eats are stellar, dining al fresco is a breeze, and there are plenty of ways to work up a sweat), there’s no denying that summer = island time. Luckily, the Casco Bay islands are just a short ferry ride from Commercial Street, allowing locals and visitors alike to take a break from the mainland, enjoy a slower pace, and get a hefty dose of vitamin sea. Check out these can’t-miss spots next time you’re island hopping.
Did we miss a spot? Let us know by emailing info@portlandoldport.com.
Peaks Island
The Inn on Peaks Island
At this well-known establishment on Peaks Island, Executive Chef Nic Saindon curated a summer menu full of seafood favorites, handhelds, and more (including a variety of gluten-free options). Whether you’re in the mood for Bangs Island mussels, stuffed lobster, or even jackfruit chili, the Inn on Peaks’ elevated coastal dining is a great choice for lunch, dinner, or a sunset drink.
33 Island Avenue, Peaks Island
Photo: Il Leone (@illeonepeaks)
Il Leone
Nestled amongst trees near the Peaks Island Lions Club, you’ll find a traditional Italian wood oven next to a nondescript trailer. Surprisingly, this spot is exactly where Ben Wexler-Waite serves up some of the best Neapolitan-style pizza in the state using ingredients sourced from organic Maine farms or ordered directly from Italy. Each pizza is fermented for 48 hours before it’s cooked at 800 degrees for just a few minutes, then served hot and fresh at the surrounding picnic tables.
2 Garden Place, Peaks Island
Island Lobster Company (@islandlobstercompany)
Island Lobster Company
When a commercial lobstering family opens up a seafood joint, you know you’re getting the freshest catch around. Soak in spectacular views of Portland with a fresh lobster roll in hand at Island Lobster Company, or book a seaside lobster bake on the Patience with your pals.
20 Island Avenue, Peaks Island
Cockeyed Gull
An island dining staple, the Cockeyed Gull offers a friendly waterfront atmosphere with an open-air deck perfect for boat-watching. Just a few feet from the ferry dock, this seafood restaurant features dishes with French and Asian influences, plus homemade desserts and a fully stocked bar.
78 Island Avenue, Peaks Island
Photo: Bab’s Cafe (@babaspeaksisland)
Baba’s Cafe
Inside a once-dilapidated 1901 Cape house, Baba’s Cafe serves up coffee drinks made from Tandem beans alongside a variety of teas and lemonade. Sweet offerings from the tiny in-house kitchen include scones, cookies, and cakes, while savory include paninis and a breakfast sandwich with caramelized onion jam and harissa mayo.
79 Island Avenue, Peaks Island
Photo: Milly’s Skillet (@joneslandingpeaks)
Jones Landing + Milly’s Skillet
This place is your one-stop-shop on Peaks Island. Jones Landing Restaurant and Bar has beer, wine, and cocktails, incredible views of Casco Bay, cornhole, and live music. During the day, you can order tacos, burgers, and snacks from Milly’s Skillet food truck to eat while handing out or on the go. For dinner, order appetizers and island plates (oysters, monkfish sticks, wings, burgers, grilled haddock and more) directly from Jones Landing Restaurant—and don’t miss the seaside fries with spicy seaweed salt.
6 Welch Street, Peaks Island
Great Diamond Island
Photo: Crown Jewel Portland (@crownjewelportland)
Crown Jewel
If you’re looking for an all-out island-themed extravaganza, Crown Jewel is the place to be. The Instagrammable interior features tropical decor, pastel pink walls, and a bright aqua countertop, and a neon flamingo sign lets you know you’re in the right spot. This women-owned island escape focuses on seafood with a twist: crab salad with blood orange and bacon, elote-style edamame with lobster, and the seasonal ceviche are fan-favorites, but the classic island burger is a great choice, too.
For an extra special treat, book Casco Bay Custom Charters’ “Pick 3” Crown Jewel Dining Charter — an all-inclusive private charter. Enjoy local beer, local hard seltzer, and wine, and a 3-course meal from Crown Jewel on Great Diamond Island. Cruise out to the island to pick up lunch or dinner, freshly prepared and waiting dockside; enjoy your meal aboard as you cruise through Casco Bay past lighthouses, stone forts, and Maine’s incredible coastline.
255 Diamond Avenue, Great Diamond Island
Photo: Diamond’s Edge Restaurant (@diamondsedgerestaurant)
Diamond’s Edge Restaurant
A seaside oasis with casually elegant waterfront dining, Diamond’s Edge Restaurant offers lunch and dinner indoors, on the outdoor deck, at picnic tables across the lawn, or at the bar. The menu includes classic seafood starters like clam chowder, coconut prawns, and crab cakes, followed by a variety of salads, pasta, and fresh fish dishes. The selection of Battery Cocktails, a nod to the island’s military history, are ideal for a warm summer evening.
Diamond Cove, Great Diamond Island
Chebeague Island
Photo: Chebeague Island Inn by Ciara Price
Chebeague Island Inn
The culinary team at Chebeague Island Inn takes advantage of Maine’s micro seasons, using the freshest local ingredients whenever possible. Part of the Prentice Hospitality Group (which also owns and operates Evo Kitchen + Bar and Twelve), this trendy spot offers breakfast, lunch, and dinner, plus Sunday brunch and “Sunset Landing,” their own version of happy hour/late night eats.
61 South Road, Chebeague Island
