The best islands in America
The coasts of America are dotted with too many magnificent islands to count, let alone summarize on a Top 12 list.
So first, our deepest, breeziest apologies to Alcatraz, Manhattan, Molokai, Key West, Whidbey Island, Isle Royale, Gasparilla, Chincoteague, Jekyll, South Padre, northern Minnesota and dozens more escape-worthy island hubs from sea to great lake to gulf to bay to shining sea — all of which will surely be featured in upcoming “best islands” travel sequels.
But, for now, we had to stop somewhere.
The following 12 offshore destinations around the nation are standouts for a variety of solid island-ish reasons: Beautiful beaches with crazy seashell collections, giant bears, no cars, bewitching bike paths and carriage roads, idyllic national parks, veritable Victorian vibes, and oyster cocktail pubs among them.
The one common point. All are worth bridge-crossing, ferry-hopping, helicopter-splurging, twin engine-braving or front crawling to savor for yourself. And they’re listed in alphabetical order, because even we couldn’t agree on a No. 1:
Floating Near: Jacksonville, Florida
Famous For: Its turbulent history and tranquil present.
Fun Times Ahead: 56th Annual Isle of Eight Flags Shrimp Festival (May 3-5, 2019)
If there’s any question where Florida really begins (or ends), it’s on this secluded speck of land at the start (or finish) of fabled State Road A1A.
Specifically, on its upper tip where Amelia Island’s single town of Fernandina Beach slumbers with its rows of Victorian mansions, pair of old paper mills, and older still cannon-lined Civil War-era garrison, Fort Clinch State Park — all oddly co-existing several miles north of the island’s Ritz Carlton (if you need it) or anything resembling mass tourism.
In its heady heyday, Amelia Island was occupied by a succession of eight different flags — French, British, Spanish, Mexican, etc. — along with an assortment of pirate banners.
What remains: genial Victorian inns, indie art galleries, seafood finds hiding under a bridge beside the Intracoastal Waterway (Down Under Restaurant), Florida’s emptiest beaches, and an assortment of fishing-sailing-manatee-watching outfitters embarking from Fernandina Harbor Marina into the blustery quiet of Cumberland Sound.
Floating Near: Los Angeles, California
Famous For: Friendly golf cart traffic and backwoods bison herds
Fun Times Ahead: 60th Catalina Festival of Art (Sept. 14-16)
An outlier of the distant Channel Islands chain, L.A.’s fabled leisure isle (26 miles off the SoCal coast) officially got off the ground when William Wrigley Jr. bought the entire 76-square-mile isle for a few million bucks sight unseen in 1919.
The chewing gum baron would promptly build a hilltop mansion here (now the storied Inn at Mount Ada), bring his Chicago Cubs over for spring training (a long gone tradition), and shape the island’s Mediterranean-style port town of Avalon into a casually refined offshore resort — luring a cross-section of Golden Age A-listers to come fishing (John Wayne, Winston Churchill), cavorting (Errol Flynn, Charlie Chaplin, Marilyn Monroe) and performing at the storied Casino Ballroom (Count Basie, Glenn Miller).
Today’s Avalon lures a broader crowd. About a million annual visitors from all over.
A quick ferry ride from the mainland (or even quicker, pricier 15-minute helicopter hop) transports guests from one of the world’s biggest megalopolises to L.A.’s offshore version of Mayberry — graced with bobbing yachts, buzzing golf cart traffic, ice cream parlors, galleries, tchotchke shops, and homey eateries & drinkeries with names like Original Jack’s Country Kitchen and Luau Larry’s.
The best-kept secret of all: the rest of the island. Nearly 90% of Santa Catalina remains a rugged preserve — featuring a wild, frothing coastline and over 40,000 acres of undeveloped interior reserved for trans-Catalina Trail backpackers, eco-jeep tourists and descendent bison herds from a long-forgotten movie shoot.
Floating Near: New York City
Famous For: Not being the Hamptons
Fun Times Ahead: Annual Local Craft Beer Festival, Pig Roast and BBQ (mid-July)
No cars. No paved roads. No Starbucks. No development along most of its parkland-protected shores dotted with, count’em, 17 sweetly-named villages — Saltaire, Atlantique, Dunewood, Cherry Grove — all sporting their own enduring charms, proud heritages, limited dining options and ironclad ordinances.
If you were a pristine barrier island hanging off the coast of imposing Long Island and just 60 miles east of that other island (Manhattan), you’d be just as protective of your precious space too.
Boasting a year-round population of about 400 that balloons to over 20,000 during summer months, Fire Island is many things to just as many visitors. LGBT and straight. Home renter families and solo Ocean Beach daytrippers. Bar-hoppers, beachcombers, zealous shorebird watchers …
There are spectacular strips of unpeopled sand here. And hiking, paddling, fishing, camping opportunities along Fire Island’s surprisingly extensive National Seashore.
There’s the riotous July 4th Invasion of the Pines, attracting hundreds of drag queens and spectators. And let’s not forget Kismet’s August clam-shucking contest, drawing its own slew of bystanders and bivalves.
However one defines and does Fire Island, the important thing is — it’s there.
Floating Near: Anchorage, Alaska
Famous For: Bears
Fun Times Ahead: Kodiak Crab Festival (May 23-27, 2019)
America’s second largest island (after Hawaii’s Big Island) has all the rugged beauty and immensity one would naturally expect from a mountain-encrusted, spruce-carpeted, fjord-injected Alaskascape tucked deep enough in the state’s temperate, archipelagic south to be nicknamed the “Emerald Isle” and “Montana at the beach.”
Home to one of Alaska’s visitor-friendliest fishing port towns (Kodiak) with a vast backyard of glacial valleys full of elk, pristine lakes hovered by bald eagles, and rivers chock full of salmon, the island’s biggest draw — literally — is its furry, 1,500-pound namesake.
The Kodiak bear is the largest sub-species of the brown/grizzly bear. Over 3,000 of them roam the Kodiak archipelago, and nowhere else.
The island’s top bucket list attraction: Booking a summer slot with one of several licensed bear-viewing outfitters in Kodiak National Wildlife Refuge to witness the ursine sockeye lunch buffet in action.
Floating Near: Mackinaw City and/or St. Ignace, Michigan
Famous For: 19th-century time travel
Fun Times Ahead: Mackinac Island Lilac Festival (June 7-16, 2019)
What’s the payoff for crossing the nerve-fraying, five-mile Mackinac “Mighty Mac” Bridge between Michigan’s Lower and Upper Peninsulas? Or skipping the bridge altogether and just hopping a 16-minute ferry to Mackinac Island from either end?
Experiencing Middle America’s best offshore Victorian time warp — complete with horse-drawn carriage rides past 19th-century mansions and War of 1812 historic sites, Afternoon Tea at the aptly-named Grand Hotel, and a quality piece of Main Street fudge.
Augment the experience by renting your own bike, horse buggy or kayak and exploring the rest of this 3.8-square-mile National Historic Landmark (80% of it is preserved state parkland) with its dramatic limestone bluffs, thick forests and out-there Great Lake waters.
Best of all, not a single Model T or Prius to be seen on the island. Cars have been banned here since 1898.
Floating Near: Boston
Famous For: Making Cape Cod seem like the big city
Fun Times Ahead: Martha’s Vineyard Food & Wine Festival (October 17-21, 2018)
Leaving the Cape’s summer bottleneck Route 6A gridlock in the dust, ditching the car in Woods Hole and ferrying the seven miles to Martha’s Vineyard isn’t exactly a secret shared by just you and Herman Melville these days.
But it’s still the perfect escape from all those waffle cone/fried clam lines on the pretty peninsula—and further proof that beautiful islands, no matter how summer crowd-inducing, always feel wondrously removed.
Massachusetts’ largest isle is home to pristine down- and up-island beaches, iconic clay cliffs, soulful Oak Bluffs ale houses, some of the smoothest coastal bike paths on either end of the Atlantic, and lots of big names for sedate little places (Sengekontacket Pond).
If you need to escape a bit further out, the beaches and cycle roads continue on Martha’s even quieter, hardier little sister, Nantucket — a swift one-hour, high-speed ferry ride away.
Floating Near: Honolulu
Famous For: Being exactly what one would expect from Hawaii
Fun Times Ahead: 96th Maui Fair (Oct. 4-7, 2018)
Who really wants to compare pineapples to pineapples and rank one dazzling Hawaiian island over another? But if we were pressed to do it, Maui’s greatest hits lineup is collectively tough to out-aloha.
Yes, there are even taller waterfalls, wilder Na Pali Coasts, gnarlier North Shore swells, bigger historic sites, eye-popping-er volcanoes elsewhere in the state — but for the whole stress-melting, beauty-seeking shebang may we direct you to the following:
Sunrise at Haleakala National Park — home of the world’s tallest dormant volcano and all-downhill 26-mile bike tour. Sunset at Kaanapli Beach — complete with daily cliff-diving spectacle.
Afternoon snorkeling at crystal clear Molokini Crater — Hawaii’s only island marine sanctuary. Halloween in Lahaina — a.k.a. “Mardi Gras of the Pacific.”
And the worthiest all-day rain forest coastal drive (to Hana) that any tropical isle could ever dream up.
MOUNT DESERT ISLAND
Floating Near: Bangor, Maine
Famous For: Legitimizing national parks east of Yellowstone and Yosemite
Fun Times Ahead: 10th annual Acadia Night Sky Festival (Sept. 5-9)
Being home to the oldest US national park east of the Mississippi and the earliest spot in continental America to catch the first direct rays of daylight is no small responsibility.
Thankfully Mount Desert — Maine’s largest island and the pin-up offshore hub of Acadia National Park — is up to both tasks. The latter from the top of 1,530-foot Cadillac Mountain (highest peak on the North Atlantic seaboard) — which sees the sun before anywhere else in the Lower 48 between mid-January to early March and again between early October through late November (it’s complicated).
Draped in A-list coastal Maine imagery and matching blueblood history at storied Bar Harbor (former summer playground of the Rockefellers, Vanderbilts, Astors, etc.) near the gates of the park, Mount Desert welcomes over three million annual visitors to rusticate at tony inns, nosh on shellfish, gallery hop, stargaze in one of the darkest available skies in the northeast, hike, bike, paddle and vanish into a network of car-free “carriage roads” financed by J.D. Rockefeller Jr.
Floating Near: Kitty Hawk, North Carolina — and Norfolk, Virginia
Famous For: Pirate lore and the term “Ocracoma”
Fun Times Ahead: Blackbeard’s Pirate Jamboree — 300th Anniversary (Oct. 25-28, 2018)
It takes some doing to reach North Carolina’s Outer Banks, home to the historic Wright Brothers flight at Kitty Hawk and a still remote-ish string of migrating sandbars set safely apart from all those Virginia-and-Myrtle-Beach-goers.
It takes even more doing to reach Ocracoke, OBX’s southernmost barrier island — tucked well below the relative crowds of Duck, Nags Head, Kill Devil Hills and Hatteras.
No bridge. No crowds. Almost no pulse — in the best sense — Ocracoke welcomes ferry (or private plane) commuters to do exactly what’s expected of anyone on a wafer-thin, 16-mile long spit of sea grass flecked, wave-pounded Atlantic shore and former Blackbeard hideout.
Put life on blissful pause.
And perhaps rent an old bicycle, browse through buccaneer tchotchke shops, idly chat with pirate impersonators, gorge through a mess of oyster shooters (beer, hot sauce, pepper, raw oyster in a shot glass) at Howard’s Pub, and then slowly pedal up a long quiet road to a vast, empty beach to nap it off.
Where else could the word “Ocracoma” (definition: “feeling relaxed and ‘oh so good'”) have been coined?
ORCAS ISLAND AND THE SAN JUANS
Floating Near: Seattle
Famous For: Making visitors wish this was a one-way trip
Fun Times Ahead: Orcas Island Jazz Festival (August 30-September 2)
Over 170 named islands and hundreds more at low tide comprise Washington’s San Juan archipelago. But, for now, a brief word on the three biggies — all accessible by the Washington State Ferry system and hampered only by crappy car lines on summer weekends.
San Juan Island, the namesake and hub of this chain, is your best bet for shopping and paddling through killer whale country.
Lopez Island, the quietest and flattest, is a magnet for cyclists.
Orcas Island, the “Gem of the San Juans,” is for wishing you could afford property here — and for driving slowly and aimlessly with the windows down on hilly, empty, sun-dappled backroads with names like “Enchanted Forest” and “Dolphin Bay.”
Then dipping through a quiet green valley dead-ending at some tiny harbor where an old man on a bicycle is walking his seven dogs along the road. Before driving up into Moran State Park and to the top of 2,409-foot Mt. Constitution for views of Mt. Rainier, British Columbia and everything in between on a clear day.
Then rolling past pottery shacks, sculpture gardens and back onto Main Street, Eastsound (a.k.a. “town”) where the ferry boat awaits near those sigh-inducing realty office window posts.
Floating Near: Fort Myers, Florida
Famous For: Serious seashells by the seashore
Fun Times Ahead: 82nd Annual Sanibel Shell Fair & Show (March 7-9, 2019)
Foraging for shells on a long, shell-strewn beach. It’s a mindless activity reserved for kids, right?
Not on the conch- and cockle-carpeted shores of Sanibel Island.
The island’s boomerang-shaped, east-west orientation (most are north-south and miss the biggest shell payloads) makes Sanibel more than just another sedate Florida Gulf community with sweet sunsets, smooth bike paths and spoonbill-stuffed wildlife refuges.
A world-class shell magnet, the sands of Sanibel are strewn with amazingly intact whelks, junonias, coquinas and murexes—and folks of all ages hunched over looking for them. Doing the well-known “Sanibel Stoop.”
From the beach, it’s a quick commute to the Bailey-Matthews National Shell Museum and myriad craft shops to admire just how many ingenious little figurines can be made from nothing but shells.
Floating Near: St. Thomas, U.S. Virgin Islands
Famous For: Resilience and Virgin Islands National Park
Fun Times Ahead: St. John Festival — a.k.a. “Carnival” (late June-July 4th)
Among the most unique hideaways in the Caribbean and singular outposts on the US National Park grid, St. John is nearly two thirds designated parkland — a tropical preserve that has stood as the perfect low-key alter-ego to its attention-hogging neighbor St. Thomas, just a 20-minute ferry ride away.
Nearly one year after suffering devastating hits from a pair of Category 5 hurricanes last September — Irma, then Maria — both islands remain in the throes of what the US Virgin Islands Department of Tourism calls a strong recovery.
On St. John, famous rustic retreats like Caneel Bay Resort remain indefinitely closed, with hopes to slowly rebuild. Signature crescents of sand like Cinnamon Bay and Trunk Bay are strikingly bare.
The promising news: all trails, beaches and roads at Virgin Islands National Park are now reported open; day-trippers from St. Martin and, increasingly, overnighters are slowly returning; healthy numbers of green sea turtles are greeting swimmers at Maho Bay; and major hotel re-openings are scheduled for the end of 2018.