Friday
Boat and bike rides

While there are private water taxis available to transport you to the island, the Casco Bay Lines ferry is the most efficient and cost-effective way to get to Peaks and runs throughout the week. Your ticket covers a round trip and traverses the bay in about 15 minutes. A short walk up a hill from the water and you’ll find yourself in front of the Inn on Peaks Island, in the middle of town. Peaks Island Marina and Jones Landing also have slips for rent if you’re traveling in your own boat.

If the Inn on Peaks is booked, which is not unusual given their business as a wedding venue, your best bet is to contact Port Island Realty, which has a good handle on available rentals. Rentals through Airbnb and VRBO are also plentiful. The entire island is very walkable, although cars are allowed and golf carts are available for rent.

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Start out by popping in at the Inn for lunch. It’s American fare with lots of very fresh seafood options. The peanut butter pie is also a favorite, although a little nap inducing for midday. Once you’ve settled, you can walk about five minutes north up Island Avenue to Brad’s Bike Rental and Repair. They’ll get you fitted up and helmeted for a ride around the island. It’s a beautiful way to get the lay of the land, and while the five-mile island loop is a bit hilly, it’s not an overly ambitious endeavor. The back side of the island, facing the open Atlantic, is especially breathtaking and invigorating. You’ll pass by Battery Steele, a military fort built during World War II to protect Portland Harbor.

Once you’ve returned your rental to Brad’s, walk across the street to Hannigan’s Island Market. While Hannigan’s functions as the only grocery store on the island, it also serves as a great resource for any Peaks-related questions or advice you might need. We suggest talking to owner Bob Hannigan or a member of his team about buying fresh lobsters for the following night; they’ll put you in touch with the right lobsterman, and by this time tomorrow you’ll have truly the freshest crustaceans Casco Bay has to offer. The market also makes a great pizza and has an impressive wine inventory.

Before dinner, spend some time just sitting outside, surrounded by water, enjoying what is guaranteed to be a magical sunset. Once it’s set, walk over to the Cockeyed Gull, which has a great Asian-influenced menu. It’s a casual spot, but if you want a table outside, we recommend a reservation.

Saturday
Exploring on water and land

In the morning grab bagels, breakfast sandwiches, and coffee at the Peaks Cafe. Once you’re caffeinated and nourished, head over to Maine Island Kayak Company to rent a kayak. They offer guide services and group and individual tours. The trip around the island can be daunting for a beginner kayaker, so they’ll help tailor the right course for your skill level. If you’d rather go out unguided, you can stay in front of the island in the sheltered Casco Bay, or make the five-mile trek around the circumference.

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After your trip, stop at the Umbrella Cover Museum. This unique, niche collection has been an island mainstay for years. Owner Nancy Hoffman has collected thousands of umbrella covers from all over the world for your perusal. After you get your cultural fill, call a water taxi and head over to the Crown Jewel restaurant on Great Diamond Island. This tiki restaurant has the best frosé in the area (although the Highroller Lobster Company in Portland gives them a run for their money), and the flamingo and palm tree decor feels delightfully out of place on the rugged island.

After your ride back, poke in to some of the Island Avenue shops. The boutique Take a Peak has lots of Peaks- and nautical-themed souvenirs, and Down Front is full of classic vacation sweatshirts and tees. Down Front is also probably the most frequented spot in town, with people making a day trip to Peaks just for one of the famous ice cream cones. A tip: the line will be long, but it moves; they have this down to a science.

Pick up your lobsters and get ready for a classic Maine lobster bake. Hannigan’s will have any extras you might need—corn, butter, potato chips, and blueberry pie—so all you’ll need is a pot. If you’ve never boiled lobster before, don’t worry—anyone on the island can lend some tips, so don’t be afraid to ask a purveyor. We suggest soft-shell lobster for first-timers.

After dinner, do as the locals do and head over to the American Legion Post for drinks and billiards. It’s not fancy, but the jukebox is stacked, the drinks are strong, and it doesn’t close until it’s ready to close. Out-of-towners can be subjected to an initial side eye, however. The Inn is also great for late-night drinks, if you’re in the mood for something a little more refined.

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Sunday
Fried clams and reggae

Snag a table at the Island Lobster Company’s patio for brunch. If you stayed a little too long at the Legion last night, the fried clams here should help. Afterward, head to the Fifth Maine Regiment Museum to learn about Maine’s role in the Civil War.

Although it’s currently postponed, Reggae Sunday is typically a tradition from Memorial Day through Labor Day on Peaks, with an abundance of drinks and great music on deck all afternoon. If you’re heading home on Sunday and want to avoid a ferry filled with revelers, we suggest an earlier boat back to Portland.