Captain Matt has walked these paths plenty and passes under the same cliffs by boat all season. Here is our practical guide to the park, plus the views you can only get from the water.

Here is how to plan a visit on foot, what you are looking at once you get there, and why the view from the water is worth adding.

At Bird's Eye Maine, Cushing is one of the islands we pass most often on the way out to the lighthouses. Here is what you will see from the water, how the island became a private summer colony, and how invited guests actually get there.

Here is how to get there, what to do and how to be a good guest in a community where everybody knows everybody.

At Bird's Eye Maine we run trips across Casco Bay from Portland's working waterfront, and Chebeague is one of the islands we head to most. Here's how to choose your landing, plan a realistic day and time the walk to Little Chebeague so you're not racing the tide.

Here is what to look for, how to plan a visit, and why the little tower is worth seeing from the water too.

Below, we walk through each season in town and on the bay, then share a few planning tips for making your dates work.

aptain Matt has spent his life on Maine water, though, so here is a local's guide to picking your month, preparing for the trip, and what you can see closer to Portland.

Here is where to look, how to tell what you are seeing, when to go, and how to watch without bothering the birds.

Here is how to plan a weekend with good food, a few drinks, time on the bay and enough breathing room that the bride actually gets to relax.

So the right beach depends less on a ranking and more on your kids: their ages, how long they last in cold water, and what they want to do once they are out of it.

So the useful way to read the bay is by island, by access, and by the time you have. The islands below are sorted that way, with the ride between them treated as part of the trip.

Which dock you land at decides almost everything else: how far the beaches are, where lunch happens, and how early you need to head back.

House Island is privately owned, so you visit by boat, and you walk it only with a booked fort tour, a rental or glamping stay, or the owners' permission; everyone else sees it from the water.

The catch is that everything depends on your boat, the weather, and the time you give yourself.

Great Diamond Island is mostly a private residential community, so the best day trip pairs a meal near the Diamond Cove dock with views of Fort McKinley and the shoreline from the water.

Long Island is a year-round island town with a sandy beach, calm roads, and a bakehouse deck, and you reach it by public ferry or private boat.

Which beach suits a swim and which suits a scramble, when to catch the boat home, and why the Backshore deserves your last hour all come down to that.

 For couples and small groups who want soft light on Portland Head Light, a good shot at calm water, and fewer tour boats around, an early start is worth it.

A good Cliff Island day comes down to the boat you choose, the spot where you step ashore, and a return time you trust. The rest is walking, a picnic, and a lot of quiet.