PEAKS ISLAND

A 15-minute ride from the Portland ferry terminal, Peaks is the most populated island, with about 3,000 residents come summertime. Once you’re off the ferry, rent bikes at Brad’s Bike Rental and Repair or a golf cart at Peaks Island Golf Carts, and head out on the island’s 3.7-mile loop road. Bring a camera: it runs past Cairn Beach (great for views, too rocky for swimming). Staying over? Book ahead at the Inn on Peaks Island (if it’s available, opt for the lovely Bailey Island Suite). If a swim or sunbathing’s on the agenda, point yourself southwest toward Sandy Beach, then wind up back near the ferry dock for shrimp tacos on the deck of the Cockeyed Gull, with its million-dollar view of Portland’s skyline.

LONG ISLAND

Plan to bring your own bike (there are no on-island rentals), or rent a golf cart at Long Island Golf Carts. Before spending a few hours on the large and sandy South Beach, grab some ethereal hand-cut cinnamon-sugar doughnuts at Byers and Sons Long Island Bakehouse. Rather spend your beach time nature watching? For that you’ll want Andrews Beach or the less crowded Fowler Beach—both are frequented by migratory birds and dolphins. Just before sunset, head to the rocky shores of Cleaves Landing on Eastern Avenue for incredible neon-streaked skies. And if you’ve planned things well, you’ll have a reservation for the Hardshell Cafe’s weekly lobster bake, hosted by Ed and Jeanie McAleney and served on their porch, complete with sea breezes.

CLIFF ISLAND

Lounging in nature is the prime directive here, and the plethora of secluded coves, deep woods, conservation land, and wildlife all make it easy. Cliff is the farthest island served by Casco Bay Lines, and the largest one in the bay with no paved roads. Cliff Island Store and Cafe is the place to find local gossip and lobster rolls. Tote the latter over to Stone Beach (aka Rocky Beach) for a picnic on the island’s southwestern edge with views of Peaks and Long Islands, or hike out to the easternmost side for sweeping vistas of the Atlantic.

BAILEY ISLAND

Technically part of Harpswell and connected to the mainland by the world’s sole cribstone bridge (made of hulking granite stone slabs), Bailey offers up miles of picturesque coastline. So, it’s an ideal place to charter a day sail with Sea Escape Cottages and Charters, jump on a lobster boat with West Wind Lobster Tours, or hike and soak up the sublime views at Land’s End on the island’s southernmost tip. Leave time to cap the day with lobster wontons and a local brew on the deck of Cook’s Lobster and Ale House.

LITTLE DIAMOND + GREAT DIAMOND ISLANDS

Fort McKinley, constructed in the late 1800s, is the focal point of Great Diamond. Since its retirement in 1945, it’s been transformed into both a tiny resort—the Inn at Diamond Cove—and private residences. Much of the island is closed to the public, but the inn offers enough amenities— from tennis and indoor basketball to a swimming pool, a yoga studio, and three dining options—that nobody much cares. The area is car-free, so if you want to explore, ask the property for a golf cart ride or a complimentary bike. Little Diamond Island next door is peppered with privately owned cottages, many of which can be rented. (At low tide, you can walk between the islands at Lamson Cove.) Meanwhile, Diamond’s Edge, an upscale restaurant perched on Great Diamond’s sparkling marina, is good enough that many visitors come just for dinner and catch the ferry home after.

CHEBEAGUE ISLAND

Whether you’re just swinging through Chebeague Island Inn for a game of golf and an excellent dinner on its breezy deck or settling in for a week full of lawn games and tennis, the inn is the island’s (relatively) buzzy hub. (Note: There are no TVs on the property, so don’t forget reading material for rainy days.) For beach visits, request the inn’s shuttle service or borrow bikes and ride over to the Niblic for ice cream made by North Yarmouth’s spectacular Toots. And this year, the inn is pushing the season by staying open longer into the fall—yet more of a good thing.

A note about on-island transportation: Only Peaks Island allows cars to be transported by ferry, and car reservations can be scarce in the summer. On most islands, bikes or golf carts are rentable near the ferry terminal, and you can also bring your own bike via ferry for a small extra cost.

Read More:

• 
  48 Hours in Cape Elizabeth, South Portland + Scarborough
• 
  Brunswick in 48 Hours
• 
  Carrabassett Valley in 48 Hours
• 
  Lovell in 48 Hours