Unearth The Voyage
New England’s coastline hides some of the most charming island escapes in America, from rocky Maine outposts to sunny Massachusetts beaches. Whether you crave car-free trails, historic lighthouses, or simply a slower pace, these islands offer the perfect retreat from everyday life. Pack your bags and get ready to explore fifteen unforgettable spots where ocean breezes and coastal beauty await around every corner.
1. Nantucket, Massachusetts
Gray-shingled cottages line cobblestone streets, creating picture-perfect scenes at every turn. Nantucket wraps visitors in old-world charm while offering more than 80 miles of sandy shoreline to explore. Families love the gentle surf on the north side, while surfers head south for bigger waves.
Hop on a bike to cover serious ground without traffic stress. The island’s flat terrain and well-maintained paths make pedaling a breeze, even for younger riders. Ferries from Hyannis run year-round, bringing both passengers and vehicles to this Atlantic gem.
Stroll through town for boutique shopping, fresh seafood, and that famous New England hospitality. Summer brings crowds, but shoulder seasons reveal a quieter, equally magical side of island life.
2. Martha’s Vineyard, Massachusetts
Six distinct towns give this island more personality than most entire regions. From preppy Edgartown to artsy Aquinnah, each village tells its own story through architecture, shops, and local traditions. The south shore unfurls miles of golden sand perfect for long sunset walks.
Lighthouses dot the coastline, offering Instagram-worthy backdrops and fascinating maritime history. Gay Head Cliffs showcase dramatic clay formations in rust, cream, and gray striations. Steamship Authority ferries connect Woods Hole to both Vineyard Haven and Oak Bluffs throughout the year.
Celebrities may own estates here, but the island maintains a refreshingly down-to-earth vibe. Rent a moped, grab some fresh clam chowder, and lose yourself in the island’s unhurried rhythm for a truly restorative getaway.
3. Block Island, Rhode Island
Towering clay bluffs plunge into turquoise waters, creating scenery more reminiscent of Ireland than southern New England. Block Island packs serious natural beauty into just seven square miles. Seventeen miles of beaches circle the island, each with its own character and crowd level.
Two-wheelers rule here, with miles of quiet backroads connecting lighthouses, beaches, and hidden ponds. High-speed ferries zip passengers from Point Judith to Old Harbor in about half an hour, while traditional boats take a more leisurely pace. Seasonal routes add even more access options during summer months.
Victorian hotels perch above the harbor, their wide porches perfect for watching sailboats glide past. The island feels both timeless and refreshingly uncomplicated, a rare combination in today’s hectic world.
4. Mount Desert Island, Maine
Acadia National Park dominates this rugged island, offering some of the most spectacular coastal scenery on the entire Eastern Seaboard. Granite peaks rise abruptly from the sea, while historic carriage roads wind through evergreen forests. Cadillac Mountain claims fame as the first spot in the U.S. to see sunrise from October through March.
Bar Harbor serves as the main hub, packed with restaurants, outfitters, and lodging options for every budget. But venture beyond town to discover quiet coves, tide pools teeming with life, and trails ranging from easy strolls to challenging scrambles. Frenchman Bay stretches out in shimmering blues and greens, dotted with smaller islands.
Unlike most New England islands, this one connects to the mainland by bridge, making access wonderfully simple.
5. Monhegan Island, Maine
Artists have flocked to this tiny speck for over a century, drawn by the dramatic light and wild coastal scenery. Cars never made it here, keeping the island blissfully quiet and walkable. Nine miles of trails crisscross the island, hugging cliff edges where waves crash spectacularly below.
Passenger ferries from Port Clyde provide the only access, running seasonally to match the island’s own rhythm. Summer brings galleries, studios, and plein-air painters scattered across the landscape. Winter sees the population shrink to just a hardy few dozen year-rounders.
Lobster boats bob in the harbor at dawn, while gulls wheel overhead calling their ancient songs. Pack light, wear sturdy shoes, and prepare to disconnect from the modern world. Monhegan rewards those seeking solitude, inspiration, and raw natural beauty in equal measure.
6. Peaks Island, Portland, Maine
Just a 20-minute ferry ride from downtown Portland drops you onto this friendly island where locals still outnumber tourists. Casco Bay Lines runs frequent boats year-round, making day trips incredibly easy. Beaches, walking paths, and ocean vistas await without any complicated planning or advance reservations.
Rent a bike right off the boat or simply wander on foot through the quiet residential streets. The island’s compact size means you can loop the perimeter in an afternoon, stopping for ice cream or fish tacos along the way. Kids love the sandy stretches perfect for castle-building and tide pool exploration.
Unlike more remote islands, Peaks maintains a lived-in, neighborhood feel that’s both welcoming and authentic. Summer cottages mix with year-round homes, creating a genuine community rather than just a tourist destination.
7. Vinalhaven, Maine
Old granite quarries now filled with crystal-clear water create the most unusual swimming holes you’ll ever experience. Vinalhaven’s industrial past left behind these deep pools surrounded by towering stone walls and shady pines. The cold water refreshes on hot summer days like nothing else.
Working lobster boats crowd the harbor, reminding visitors that this remains a genuine fishing community, not a manufactured tourist destination. Pine forests cover much of the island, crisscrossed by quiet roads perfect for exploring by bike or car. The Maine State Ferry Service runs vehicle ferries from Rockland, making multi-day stays practical.
Local restaurants serve lobster rolls and blueberry pie that taste even better after a day of island adventures. Vinalhaven moves at its own pace, unhurried by mainland pressures or tourist expectations.
8. Isle au Haut, Maine
Wild doesn’t begin to describe this remote chunk of Acadia National Park floating off the mainland. Isle au Haut sees a fraction of the visitors that crowd Mount Desert Island, preserving a pristine, backcountry atmosphere. Rugged trails wind through dense spruce forests and along rocky shores where seals haul out on ledges.
Year-round passenger ferries depart from Stonington, with seasonal service extending to Duck Harbor for hikers and campers. No vehicles make the crossing, keeping the island’s five-and-a-half miles of road blissfully quiet. The tiny village clusters near the town landing, while the rest remains beautifully undeveloped.
Serious hikers come prepared for challenging terrain and changeable weather. Those willing to make the effort discover one of New England’s most spectacular and least-visited island treasures.
9. Star Island, Isles of Shoals, New Hampshire
History soaks into every stone of this remarkable island conference center nine miles off the New Hampshire coast. Star Island has hosted religious and educational retreats for over 150 years, creating a unique atmosphere unlike any other New England destination. Day visitors can join walking tours to explore the historic buildings and dramatic shoreline.
Boats operate seasonally from Portsmouth and Rye, bringing curious travelers to this windswept outpost. The island’s stark beauty and sense of isolation create a contemplative mood that lingers long after departure. Seabirds nest on the rocky edges, while harbor seals pop up in the surrounding waters.
Limited overnight accommodations fill quickly with conference attendees, but day trips offer plenty of time to soak in the special character of this place. Bring a jacket since ocean breezes blow strong even on warm days.
10. Spectacle Island, Boston Harbor, Massachusetts
Boston’s skyline rises dramatically across the water, providing one of the best urban views anywhere while your toes dig into actual beach sand. Spectacle Island transformed from landfill to recreational paradise, now offering hiking trails, swimming, and picnicking just minutes from downtown. Public ferries run May through October, making this an easy summer escape.
Climb to the island’s twin drumlin peaks for panoramic vistas stretching from the city to the outer harbor islands. The lifeguarded beach operates during summer season, perfect for families wanting a quick ocean dip without driving to Cape Cod. Visitor center staff share the island’s remarkable transformation story.
Pack a lunch since food options are limited, and bring plenty of water for hiking the exposed trails. Few visitors realize such a peaceful retreat exists so close to a major city.
11. Plum Island, Massachusetts
Birders arrive with binoculars and field guides, knowing Plum Island ranks among the top spots on the Atlantic flyway. The Parker River National Wildlife Refuge protects most of this barrier island, preserving dunes, salt marshes, and beach habitat for hundreds of species. Spring and fall migrations bring spectacular variety, from piping plovers to snowy owls.
Miles of sandy beach stretch along the ocean side, though some sections close seasonally to protect nesting shorebirds. Check refuge updates before visiting to avoid disappointment. The island connects to the mainland near Newburyport, making access simple by car.
Summer weekends see parking lots fill early, so arrive before 10 a.m. or come on weekdays for a more peaceful experience. Even non-birders appreciate the wild beauty and sense of nature thriving just beyond the suburbs.
12. Cuttyhunk, Elizabeth Islands, Massachusetts
Population drops to just a few dozen hardy souls once summer visitors depart from this westernmost Elizabeth Island. Cuttyhunk delivers that genuine end-of-the-world feeling increasingly rare in developed New England. Quiet dirt roads, a tiny harbor, and sweeping ocean views create an atmosphere of peaceful isolation.
Ferries and water shuttles run from New Bedford on seasonal schedules, so plan carefully to avoid getting stranded or cutting your visit short. No cars make the crossing, keeping the island wonderfully tranquil. A handful of seasonal rentals and the Cuttyhunk Fishing Club provide limited lodging options.
Gosnold, the town encompassing Cuttyhunk and the other Elizabeth Islands, ranks as Massachusetts’ smallest municipality by population. Bring supplies from the mainland since island shops stock only basics. Those craving true remoteness will find it here in abundance.
13. Prudence Island, Rhode Island
Narragansett Bay’s largest island moves at a pace that seems borrowed from a gentler era. Prudence Island attracts those seeking genuine quiet rather than resort amenities or bustling beach scenes. Salt marshes edge much of the shoreline, creating prime habitat for herons, egrets, and other wading birds.
Vehicle and passenger ferries run year-round from Bristol, serving the small but dedicated community of island residents. Dirt roads wind past modest homes and through wooded areas where deer browse fearlessly. A few small beaches offer swimming, though most visitors come for the overall atmosphere rather than specific attractions.
Bring bikes to cover more ground, since the island stretches about seven miles long. Limited services mean packing a picnic and planning ahead. Prudence rewards those who appreciate subtle beauty and unhurried exploration over splashy entertainment.
14. Grand Isle, North Hero & South Hero, Vermont
Lake Champlain’s island chain offers a completely different flavor from ocean-focused New England getaways. Vermont’s Lake Champlain Islands stretch north toward Canada, connected by bridges and causeways that make island-hopping wonderfully easy. Grand Isle State Park provides camping, swimming, and boat access with the Green Mountains rising to the east.
Alburgh Dunes State Park protects a rare sand beach and dune system, perfect for families wanting gentle water and shallow swimming. Bike routes follow quiet farm roads past orchards, vineyards, and historic barns. North Hero and South Hero maintain that classic Vermont charm, with country stores and farm stands selling local produce.
Summer brings warm lake temperatures ideal for paddling, fishing, or simply floating. Fall foliage rivals anything inland, with fewer crowds to compete with for views and photo opportunities.
15. The Thimble Islands, Connecticut
Dozens of tiny pink-granite islands scatter across the waters off Branford like pieces of a giant’s puzzle. The Thimble Islands range from bare rocks to substantial islets hosting summer cottages, each with its own quirky name and story. Only a handful remain inhabited year-round, giving the archipelago a storybook quality.
Narrated boat tours departing from Stony Creek provide the classic way to see these photogenic gems. Captains share tales of pirate treasure, eccentric owners, and the geology that created the distinctive rose-colored stone. Kayakers can paddle among the islands at their own pace, discovering hidden coves and dramatic rock formations.
Captain Kidd supposedly buried treasure here, though nobody’s found it yet. The islands glow especially beautiful at golden hour when the granite catches the warm light and seems to blush even pinker.
