Set Sail & Discover Maine Islands

Maine islands break the mold of what we traditionally think of as an offshore escape. To be fair, so does much of the coastline. That’s just what draws people to any shore of Vacationland – that raw, rugged, fearless appeal. Who needs tropical when you have untamed islands? 

Depending on how you count islands, Maine either has 4,613 or 3,372. We’re going with the latter since that’s the official Coastal Island Registry number. In any event, among those thousands of islands, there are a couple of dozen worth considering for your Maine itinerary. 

In a state where island ownership is 54% private and 40% state-owned, with the rest falling into other categories like the 49 offshore islands overseen by the National Wildlife Refuge, narrowing it down to one or two to visit can seem daunting. We’ll make it a little easier for you. Plus, we’ll reveal some lesser-known ways to see more islands in less time. 

The Famous 15 Islands of Maine

One of the best places to start is the Famous 15 group of islands, meaning those with year-round residents plus tourism appeal. We’ll start from the largest population to the smallest. 

Vinalhaven Island

Population: 1,165

The midcoast Maine island of Vinalhaven isn’t just the most populated; it’s also the largest. Together with its sibling island of North Haven, they are known as the Fox Islands. 

Ferries leave out of Rockland to take the 15-mile one-hour ride to Vinalhaven for residents who commute and tourists looking to get off the mainland. You can ferry a car, but you don’t need to if you like to get around by bicycle or don’t mind walking.

The island is one of the largest lobster fleets in the world, which gives an air of authenticity then backed by stunning natural beauty. From the dock in Vinalhaven (the town), you can explore the shops and restaurants and then head off to see beaches, a Brown’s Head Light Station, or one of the quarry swimming holes. 

Vinalhaven Land Trust has dozens of trails and sites to explore, and one of our favorites is Tip Toe Mountain.

Peaks Island

Population: 1,000 year-round, 3,000 during summer

As part of the city of Portland, Peaks Island isn’t as much of a tourist destination as it is an additional neighborhood to explore. Once upon a time, the island had more of a carnival atmosphere. Now, it’s a welcome break from the “big city” of Portland. 

One of the best reasons to visit Peaks Island is Cairn Beach. The best way I can explain it is that it seems like a gothic Lego game with pieces you can pile together and long slabs of bedrock. Swimming is too dangerous here, but Peaks Island also has Sandy Beach, where you can walk top Catnip Island at low tide. 

Access to Peaks Island is from Old Port in Portland, using the Casco Bay Lines ferry service. No car is needed; the island is walkable. In fact, a trail guides you around the perimeter, coming in just under four miles.

NOTE: Many of these islands have opportunities to walk to another island at low tide. Please understand that timing the tide wrong could leave you stranded on an island until the next low tide. 

Islesboro

Population: 566 

Sitting in the center of Penobscot Bay, Islesboro is 14 miles from tip to top, with the nearest port being three miles away in Lincolnville. The quick 20-minute ferry trip drops you off near the Grindle Point Sailors’ Museum and Lighthouse. 

The escape to Isleboro is more about the undeveloped land than the nightlife or charming storefronts. It’s a place so endearing that superstars like John Travolta and his late wife Kelly Preston raised a family there. Kirstie Alley introduced the two to the island after moving there in 1993. She sold her home in 2020, a few years before she passed away. 

The Islesboro Land Trust has numerous properties here to explore, from wooden walkways over bogs to Mount Desert Island-type views without any crowds to lush wild blueberry fields. Turtle Head Preserve is a must-see in Islesboro. 

Those with a boat (or epic paddling skills) can visit the even more remote Warren Island State Park. A dozen campsites and three shelters make a nice overnight retreat. Quicksilver Water Taxi can also take you there and back.  

North Haven

Population: 355 

You’d think, as the other half of the Fox Islands, that North Haven would be connected by bridge to Vinalhaven, but it’s not.  A local boat company offers ferry service to and from North Haven to Vinalhaven.

As the quieter cousin to Vinalhaven, you’ll still find unique activities here. This creative community is compared to the art colonies in Ogunquit and Monhegan. Rarely would I recommend going to a gift shop as a waypoint, but the North Haven Gift Shop specializes in local artworks and Maine-made items. 

You might find your own artistic inspiration at the properties of North Haven Conservation. At low tide, walk over to Burnt Island and explore the pedestrian trail around the tidal flats.

North Haven Oyster offers tours, including a chef’s tour that enticed Gordon Ramsay to visit. 

Chebeague Island

Population: 341

People usually visit Chebeague Island for one of two reasons: to stay at the Chebeague Island Inn or to play golf at Great Chebeague Golf Club, with ocean views at every hole. Ferry service is available from Littlejohn Island or after island hopping Casco Bay Ferry from Portland. 

Another low-tide walking adventure awaits at “The Hook,” where you can cross over to Little Chebeague Island in its raw, natural form. A mix of sandy beaches and pine-topped cliffs await on different ends of the island. Sunset Beach is a great place for the, well, sunset. 

The town triples in size over the 4th of July holiday, making it a perfect place to celebrate among your new island friends. This is about as friendly as islanders get. 

Swan’s Island

Population: 332

This Downeast treasure is easily accessible from Bass Harbor on Mount Desert Island with a 40-minute ferry ride. The ferry does allow cars, but make a reservation to be sure there’s room. However, with 20 miles of roads that are all bicycle-friendly, bringing two wheels is more affordable and less of a hassle.  

One of the coolest things to do on Swan’s Island is stay at the Keeper’s Apartment at Burnt Coat Harbor Lighthouse. Explore the water, from lighthouses to puffins, with a trip through Swan’s Island Charters. Two miles of trails surround the lighthouse, and four public beaches are spread throughout the island. Fine Sand Beach is worth the trek to experience. 

Another stop should be the Swan’s Island Lobster and Marine Museum. Follow the Facebook page because, in this part of Maine, having a website isn’t a priority. 

Long Island

Population: 230

Access to Long Island can be reached by Casco Bay ferry service from Great Diamond Island or Chebeague Island. In contrast to the Long Island of New York, this one offers so much New England laid-back energy that I’d recommend staying at least one night. 

Several beaches are worth exploring, from the high-energy waves of Wreck Cove to the double-crescent curve of Fowler’s Beach. Walk the rocks of Cleaves Landing or soak in views from Flat Rocks. 

You also get the signature lobster roll restaurants, breakfast bakery, and ice cream stand on this enchanting island. 

On a particularly foggy day, go to the Folwer Beach shoreline looking toward Pumpkin Head and see if you can spot the Ghost Ship of Casco Bay. 

Great Diamond Island

Population: 91

The name hints at the island’s more elite status, as Great Diamond Island holds more private property than public beaches you’ll find on other islands. 

The highlight is staying at the Inn at Diamond Cove. You’ll get more access to the waterfront while also being able to explore the elusive Sea Glass Beach that is off-limits to non-hotel guests. 

As a lighthouse aficionado, it’s only fair to tell you that the Echo Point Lighthouse (aka Pocahontas Light) is the world’s smallest lighthouse, standing just six feet tall. It’s best viewed from a boat (with binoculars). Keep an eye out just before you dock. 

At low tide, a sandbar connects to Little Diamond Island, another small community with private homes and beaches. 

Matinicus Island

Population: 74

When you really want to get away from it all, go to Matinicus. I should probably prepare you for a few things first. You really need to know what you’re getting into, as the locals have little patience for tourists who want the benefits of Kennebunkport 22 miles out to sea. 

At the outermost stretch of Penobscot Bay’s fingertips sits this island, exposed to all the elements year-round. The island itself is nearly as primal, with limited use of electricity, tap water, and indoor plumbing. Matinicus is happily stuck in a different era and has no grocery stores. 

The ferry from Rockland will get you there on a 23-mile, more than two-hour ride through rough waters. You can’t go on a ferry day trip here because the ferry leaves an hour after it arrives and – at best – comes back two days later. Otherwise, you’ll be waiting for 2-3 weeks. Look at options through Penobscot Island Air if the ferry isn’t right for you or rent a private charter.

Matinicus’s reputation is that of piracy, turf wars, and feral survival. What they don’t tell you is how this remote island steals your adventurous soul with fine sand beaches, boat tours to see puffins at Matinicus Rock, and long walks to coastal treasures. Did I mention there are no cars on Matinius?

Isle au Haut

Population: 73

Samuel Champlain called it “High Island,” which we know today as Isle au Haut. The island’s year-round residence dates back to the 1800s, while early landowners handed over part of the island to Acadia National Park. This can be a bit confusing for first-timers, as the island is between Mount Desert Island and Swan’s Island/Frenchboro. The ferry departs from Stonington on Deer Isle.

You’ll find Duck Harbor Campground, part of Acadia, located here, with five sites seasonally available from mid-May through mid-October. More than 20 miles of trails wind through the Acadia section, while 

The other half of the island is the town of Isle au Haut. In just 12 square miles, you get the remoteness of Matinicus without the sinister stories and infrequent options to leave. At the same time, this is still an escape to the wilds of Maine’s islands. 

Hiking almost always requires bouldering or walking on slippery rocks. Tourist amenities are limited to keep the wilderness waiting for those who love to explore. The Isle au Haut lighthouse will be open for tours after restoration, but the boat tours will go right by this 1904 Victorian design beacon. 

When you truly want to escape the crowds of Acadia National Park, you’ll have many of these trails to yourself. 

Cliff Island

Population: 71

As one of the island residents said, “The only people who get it are the people who have been here for a long time.” Cliff Island is a slender island with a “handle,” making it look like a rough outline of a water gun. 

It’s easy to get to Cliff Island as the last stop on the Casco Bay Ferry, but it’s not easy to get a place to stay. Generations of families have homes here, and rentals are hard to come by. Most of the land is either privately owned or not open to the public for one reason or another. 

For those with a private boat, look east to Jewell Island, where the undeveloped state-owned land offers more to do than Cliff Island. Across 221 acres, you can camp atop cliffs, walk through remnants of World War batteries, or hang out among the rocks of Punchbowl Cove. Three miles of easy trails thread across the island. 

Islesford/Little Cranberry Island

Population: 70

Little Cranberry Island is part of the Cranberry Isles off the coast of Mount Desert Island. 

The town of Islesford can often be confused with Isle au Haut since this island is closer to the largest section of Acadia National Park. 

Boat routes here depart from Northeast Harbor on Mount Desert Island. Just one slice of Acadia National Park property is on the island at Isleford Historical Museum. 

An easy walking trail takes you to the rocky Gilley Beach, but that’s less than two miles out and back. Go for the history and scenery, but you won’t need more than half a day here unless you want to get a rental and enjoy island life and simple seaside pleasures. 

Monhegan Island

Population: 69

The name means “Out to Sea Island in the Abenaki language, and that’s just what you get on this amazing island that should be on your short list of Maine islands to visit. Monhegan Island is one square mile in size and mountainous enough for the lighthouse to be perched atop the island, not at the shore. 

Thomas Edison’s son Theodore had the bright idea to conserve the land here to prevent it from being developed. At the same time, a vibrant art colony was growing, with works now on display at the Monegan Museum of Art & History. Monhegan was so inspiring to artists that all paintings reflect a view you can easily find while visiting the island. 

More than 12 miles of trails meander across the island to some of the tallest cliffs in all of Maine. To give you an example of the risks at the headlands, signs and brochures will warn that “A rescue would be impossible.” Cliff Trail wraps around the island, including Pebble Beach, with one of the best sunrise views and a shipwreck on the south end of the island.

Swim only at Fish Beach, set among the lobster houses that long served as the economic boost to keep Monhegan afloat, or Swim Beach. They both sit on safer waters facing the harbor.

Before the trip back, have a drink at the Monhegan Brewing Company. 

Frenchboro

Population: 61

Maine has a thing with naming many locations Long Island or Long Lake, so you should know that Frenchboro is a town on a different Long Island than the one in Casco Bay. Locals call it Outer Long Island. 

Frenchboro is surrounded by Blue Hill Bay in the Downeast region, with views of Swan’s Island and Mount Desert Island. You can pair the trip with a stop at Swan’s Island if you’d like. 

Nearly 14 miles of hiking trails extend to remote Maine cliffs and beaches, but be sure to take the exquisite walk through Cathedral Woods, which includes a Fairy House Forest. Two large beach areas await on the north and south end of the island. Eastern Beach is the best approach for those with private boats. 

Frenchboro and Outer Long Island are only for day trips, as no hotels or rentals are available here, and most of the island is wilderness. 

Great Cranberry Island

Population: 40

On a clear day, you’ll get amazing views of Acadia National Park on Mount Desert Island, including the high point of Cadillac Island. True to its name, cranberries peak in the fall. 

A trip to Cranberry Island is rewarding for those who want a short, easier hike to reap the rewards of a remote Maine beach. Cranberry Shores trail takes you to a rocky, rugged beach, while Preble Cove is a more traditional beach with small rocks instead of sand.  

This is another island that is only open for day trips, as camping isn’t allowed, and no hotels are available. 

Other Unique Maine Islands Offshore

Baker Island

Another one of the Cranberry Isles is Baker Island, and while it’s part of Acadia National Park, you can only get there on a ranger-guided tour. That trip will take at least half a day, but it’s worth it to see the lighthouse, homestead, wildlife, and shipwrecks on the island. 

The tour scoots along the edge of Otter Cliffs, Great Head, and Sand Beach at Acadia National Park on the way back to Bar Harbor. Look for sea caves if you’re boating at low tide. 

Mount Desert Island

For most, Mount Desert Island needs no introduction. It holds the popular communities of Bar Harbor, Southwest Harbor, Seal Harbor (Martha Stewart’s Maine home), and Northeast Harbor. Cadillac Mountain is the highest point on the island, and the famed Park Loop Road and carriage roads of Acadia National Park rope through the splendid natural settings. However, you do drive to Mount Desert Island through Ellsworth. 

Great Duck Island

This Downeast island has almost gone entirely to the birds, except for one rental that makes a perfect Maine experience for those seeking solitude. Most of the island is owned by the Nature Conservancy and College of the Atlantic.

The Great Duck Island House is available to rent and can fit four adults and two children. This remote island still gets mobile service, though you’ll likely leave them inside to enjoy the stunning sunrise and sunset views. 

Deer Isle/Deer Island

If you’re still scratching your head about how Maine can have so many islands, simply look at the footprint of Deer Isle and Little Deer Isle, with dozens of land formations poking out of Penobscot and Jericho bays.  

Access to both islands is available by car, and it’s worth going all the way to the southern tip at Stonington. You can also take the Deer Isle Canoe Trail to explore the waterways and hop ashore at any beach. From Sand Beach, several islands are walkable at low tide or easy to paddle to in a relatively safe harbor.

Bailey Island

Heading south from Brunswick, you’ll eventually drive over the world’s only remaining cribstone bridge carrying automobile traffic at the Baily Island Bridge. A highlight of this end of town is the Giant’s Stairs formation, with huge ledges leading down to the waterfront. 

It’s worth getting ahead of the questions you will have when researching Bailey Island. Yes, there was a fatal shark attack in Mackeral Cove in 2020. We cannot stress enough how rare of an event this was. Even one of the foremost experts on Maine’s marine life stated, “It’s not something we ever would have considered in Maine waters.”

Squirrel Island

Covering 130 acres, Squirrel Island is home to about 100 cottages used as a summer colony. A public boardwalk circles the island, but that’s about as much as the general public will be able to do if they take the ferry from Boothbay Harbor. If you do go, please know that walking is the only way to get around. Even bicycles are not allowed on the trail. 

Damariscove Island

Boothbay Region Land Trust oversees Damariscove Island, which is about three miles south of Squirrel Island. Private boats are the only way to get there, and only the southern end is open to hiking. No camping is allowed, but boats can stay in the cove for 24 hours. 

Mackworth Island

Just off Route 1 from Falmouth, a bridge connects to Mackworth Island State Park. This was once the summer home of Governor Percival C. Baxter (of Baxter State Park fame). A trail just over one mile long circles the island with a forest in the middle and another Fairy House Forest. 

The Baxter School for the Deaf is also on the island. It’s worth mentioning that the pet cemetery for Governor Baxter’s dogs and horses sits on the east side of the island. He loved his dogs so much that when one passed away, he ordered the flags at half-staff, marking the only time in American history. 

Great Wass Island

Despite being connected by road to the mainland, Great Wass Island is still the farthest island out to sea in Downeast Maine. You’ll drive through Beals Island on the way. Nature Conservancy protects Great Wass Island. 

A nearly five-mile trail forms a loop, but this isn’t for the faint of heart or those with little hiking experience. You’ll walk through bog boardwalks and an unmarked shoreline trail that is often covered in fog. 

If you’re lucky, you’ll share a view with sea lions or spot a whale on the horizon. This is where the Bay of Fundy and the Gulf of Maine meet, so swimming is not advised. 

NOTE: Several reports say part of the trail is off-limits due to private owner limitations, so call ahead to ensure this route is open when you take the trek. 

Bar Island

This island put the “Bar” in “Bar Harbor.” You have about 3-4 hours to walk to this Bar Island from Mount Desert Island before the tide swells back, covering the land bridge for nine hours. The hike can take up to 90 minutes, so plan with the tides to make it back on time. The hike is just under two miles. 

Saint Croix Island

This island between Calais, Maine, and Canada marks the first footprints of French settlers in the early 1600s. The island itself is not open to the public in any capacity. The Saint Croix International Historic Site visitor center with views of the island is on the mainland and overseen by the National Park Service. 

Hog Island

While there are at least two Hog Islands off the coast of Maine, this one sits just offshore from Brooklin. The Maine Coast Heritage Trust runs Hog Island, and access is available by boat or kayak. The island was owned by the family of “Charlotte’s Web” author E.B. White, and they donated the land for you to be able to explore. 

Two campsites, granite cliffs, and several pocket beaches are open to explore. 

Eagle Island State Historic Site

One of the outer islands of Harpswell, Eagle Island State Historic Site is an easy three-mile water taxi ride. About a mile and a half of trails cover the island, but bird nesting season can limit access through July.  

While you’re here, tour the summer home of North Pole Adventurer Admiral Robert Peary. As an interesting historical note, it was Peary’s adventure with Donald MacMillan wearing L.L. Bean’s “new” boots in 1921 that helped make them an outdoor staple. 

Moose Island

Just seven miles off Route 1 in far Downeast Maine is Moose Island, home to Eastport. Mustard fans shouldn’t miss Raye’s Mustard Mill Museum and small-batch crafted mustard. Shackford Head State Park offers amazing coastal views through forests and pocket beaches and cliffs. 

Sears Island

The midcoast Sears Island is connected by a long bridge, which opens the door to four seasons of island exploration. Enjoy vibrant wildflowers, cross-country skiing, coastal views, wildlife, and historic buildings throughout the island’s five miles of trails. More than 220 bird species have been spotted here. Clamming is allowed with a license from Searsport. Visitors enjoy new-growth forests and variations of the class Maine shoreline.

Grand Manan Island

Grab your passport to visit Grand Manan Island, just off the Downeast town of Lubec. Grand Manan is best explored as part of a Quoddy Loop Tour. Everything you love about Maine is on this island, from whale watching to lighthouse tours to steep sea cliffs. It has a landscape similar to that of Channel Islands National Park off the coast of southern California. You’re almost guaranteed to score sea glass at the beaches. 

Campobello Island

Campobello Island is a Canadian island in the province of New Brunswick, located just across the border from Lubec. It is most famous for being the summer retreat of President Franklin D Roosevelt between 1921 and 1936. 

His 34-room cottage and surrounding land are now preserved as Roosevelt Campobello International Park which serves as a monument and attraction with natural trails and beaches. The island has a rugged natural landscape, with walking trails, stretches of sand beach lined by tidal pools, and abundant wildlife.

Machias Seal Island

Machias Seal Island is a small, uninhabited island located in the Gulf of Maine, roughly 15 miles offshore from the town and port of Cutler, Maine. The island is a disputed territory between the United States and Canada. 

The only way to get here is on a puffin tour offered by Bold Coast Charter Company. The boat ride is choppy, and you’ll be under the supervision of the tour guide at all times. At the same time, this is one of the only ways to get this close to puffin colonies. 

Anchors Away

For those considering a boat trip through Maine, check out the Maine Island Trail. It covers 375 miles from Kittery to Cobscook Bay. Along the way, 250 islands are open to explore or spend a night camping under the pristine skies. 

Another great way to see some of the best Maine islands is by taking the Mailboat Run on Casco Bay Lines. You’ll ride with the people who deliver mail to the islands through the Diamonds, Long Cliff, and Chebeague islands on a nearly four-hour adventure for less than $20. The best part? This runs year-round, weather permitting, with three trips daily.   

When visiting Maine islands, be sure to practice the 7 Leave No Trace Principles and take all trash with you. Many land trusts include a mix of public and private land, so treat each nature area as you would want guests to treat your backyard. 

Some islands won’t have public trash cans. Others won’t have clean tap water. Make sure you know what to pack before you head to the island of your choice. Don’t forget to know the tide schedules before you get out of mobile phone range. Bon Voyage!