Claude AI
The Other Islands
What You Gain, What You Lose, and What Doesn’t Come With You
Carlos Mendoza • April 21, 2026
It’s April on Nantucket, and while the mainland is flirting with spring, the island is still locked in the Atlantic's cold embrace. We've survived the darkest of winter days, but let’s be honest, every February, you think about it. You’re standing in the Stop & Shop aisle, looking at a $9 jar of artisanal pickles, and you may wonder, is there somewhere else?
Somewhere where the median home price doesn’t look like a phone number for an international calling card. Somewhere where conservation land isn't just a fancy way of saying, you can’t build a shed, but the deer are free to decimate your entire vegetable garden.
You want the Nantucket soul, the isolation, the salty history, the feeling that you’re living on a very expensive raft without the feeling that you’re one property tax hike away from living in a literal basement on Pleasant Street. If you’re looking to jump ship, but you aren't quite ready to dust off the passport or learn how to navigate the tax laws of the Cayman Islands, here is the curated list of where a Nantucket refugee might actually find a home — no passport needed.
The Others
• Block Island
• Gasparilla Island
• St. John, USVI
• Vieques, PR
• Mackinac Island
• San Juan Islands
• Catalina Island
• Ocracocke Island
• Vinalhaven
• St. Croix, USVI
Property listings are current at the time of publication.
BLOCK ISLAND, RI
Typical: $2,990,000, 5 bd 4 ba, 5,484 sqft
The Little Sister
It’s Nantucket without the full weight of Nantucket — similar ferry, same fog, just a little less pressure on everything, including the price.
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The Vibe: A literal Pork Chop of rolling hills and dramatic bluffs 12 miles out at sea. There are no traffic lights, no brand-name coffee shops, and the only rush hour is the ferry arrival. It’s where the wealthy go to wear the same salt-stained hoodie for three days straight.
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The Conservation: Nearly 44% of the island is protected open space. It’s a maze of stone walls and The Greenway trails that make you feel like you’ve been dropped into the Scottish Highlands, all with fantastic clam chowder.
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The Cost: High-stakes entry, but a bargain compared to the Hamptons. Entry-level starts around $1.6M, while prime oceanfront estates command $7M+.
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The Verdict: It’s Nantucket without the dress code. You’re trading manicured hedges for wild bayberry and seeing-and-being-seen for actually seeing the horizon.
Entry: $1,775,000, 3 bd 3 ba, 2,304 sqft
GASPARILLA ISLAND, FL
Typical: $4,500,000, 4 bd4 ba, 2,301 sqft
Entry: $2,250,000, 3 bd 3 ba, 3,057 sqft
The Continental ACK
For the person who says, "I love the pedigree, but I’m finished with the frostbite."
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The Vibe: It's a seven-mile sanctuary of old-world Florida where the Old Money of the Midwest and the Northeast goes to hibernate. There's no traffic lights, no gas stations. It’s a quiet, sun-bleached enclave of manicured hedges and white-slack formality that feels like a country club detached from the mainland.
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The Conservation: Formidable. The GICIA is the island's iron-fisted protector, buying up land specifically to keep it empty. Between the state park at the southern tip and a bike path that runs the length of the island, the greenery is as strictly guarded as the social registers.
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The Cost: This isn't an escape from the prices, it’s a lateral move. Entry-level starts around $1.5M, while Village homes and Gulf-front estates command $6M to $20M.
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The Verdict: It may be the only place on the list that matches Nantucket’s curated, everything-in-its-place aesthetic. You aren't buying a bare bones lifestyle here, you’re buying the exact same high-society shorthand, just traded in for tarpon fishing and 75-degree Decembers.
ST. JOHN, USVI
Typical: $1,950,000, 4 bd 5 ba, 3,853 sqft
Entry: $638,000, 2 bd 2 ba, 1,820 sqft
The Wild Child
Maybe you’re tired of the Atlantic’s grey-blue mood swings. You want Technicolor.
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The Vibe: St. John is the ACK of the Caribbean, but with the volume turned up. Roughly 60% of the island is National Park, the ultimate conservation flex that keeps high-rises and neon lights off the horizon. If you move to the Coral Bay side, you’ll find that same 'us against the world' islander grit, just traded for wild donkeys, roaming goats, and a social scene where a salt-stained t-shirt is the only dress code.
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The Passport Factor: None. You’re still under the Stars and Stripes, though the mail takes three weeks and the island time makes the Steamship Authority look like a Swiss train schedule. You’ll swap the cobblestones of Main Street for hair-raising switchbacks and the constant, rhythmic sound of tree frogs.
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The Cost: Entry-level condos or inland lots start around $700K, but the typical hillside villa with a North Shore view runs $1.8M to $3.5M. For a prime estate, you’re back in the $8M to $30M stratosphere, with views that makes you forget you ever lived in Massachusetts.
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The Verdict: The most compelling rehab for a Nantucket addict. It is one of the few places on earth that matches ACK’s psychological distance from the real world while offering a total sensory overhaul. You keep the 30-mile-out-at-sea isolation, you just lose the frostbite.
VIEQUES, PR
Prime: $2,480,000, 3 bd 3 ba, 3,000 sqft
Entry: $650,000, 4 bd 4 ba, 1,964 sqft
The Untamed Cousin
If St. John is the rehab for a Nantucket addict, Vieques is the off-grid escape for those who find St. John too curated. It’s raw, rustic, and perhaps one of the Caribbean’s best-kept secrets.
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The Vibe: Decades of Navy use spared the island from San Juan’s high-rises, leaving behind a massive National Wildlife Refuge and pristine beaches. There are no traffic lights; wild horses own the roads, and the Bioluminescent Bay provides a neon glow-in-the-dark shoreline.
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The Passport Factor: Zero. You’re in Puerto Rico, but the mental distance is vast. You trade the Cape Air flight for a San Juan puddle-jumper or a rugged ferry from Ceiba. You swap Nantucket’s manicured hedges for wild sea grapes and cars that have never seen a wash.
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The Cost: $450K buys an inland casa, $1.2M to $2.5M lands a hillside architectural villa. Prices are rising as the rental market begins to see seasonal spikes, but old island deals still exist.
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The Verdict: A The pivot for those who find Nantucket too much. You keep the 30-mile-out isolation but trade the Range Rover traffic for a horse-drawn jam and a cold Medalla on an empty beach.
MACKINAC ISLAND, MI
Typical: $1,695,000, 6 bd 3 ba, 3,100 sqft
The Purist's Pick
For the person who says, "I love Nantucket, but I wish there were even fewer cars and more fudge."
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The Vibe: No cars. Period. It’s horses, bikes, and a seasonal economy that makes our July-August rush look like a sleepy Sunday. It's a time capsule held together by Victorian architecture and sheer Midwestern willpower.
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The Cost: It’s a tight market, but more approachable than the Grey Lady — think $1M to $4M for something historic.
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The Verdict: If you live for the Nantucket in 1950 nostalgia, this is your ghost ship. Just be prepared for the fact that the ocean is replaced by a Great Lake, which is basically the ocean without the salt or the sharks.
Entry: $839,000, 3 bd 3 ba, 1,560 sqft
SAN JUAN ISLANDS, WA
Typical: $2,925,000, 5 bd 4 ba, 3,411 sqft (Orcas Island)
The Pacific Version
This is the big one. If you want the maritime soul but you’re tired of the Atlantic’s attitude, the San Juans are the Pacific Northwest’s answer to the Grey Lady.
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The Vibe: It’s a choose-your-own-adventure archipelago. Orcas Island is the Emerald Isle (hilly, green, mystical); San Juan Island is the social hub (Friday Harbor is your version of Town); and Lopez Island is the Friendly Isle (where everyone waves at your car).
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The Conservation: Intense. The San Juan Preservation Trust is basically the local deity. You get old-growth forests, bald eagles, and orcas instead of seals.
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The Cost: $1.2M gets you a solid island house. For a waterfront compound that makes you feel like a Bond villain? $3M to $10M.
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The Verdict: It’s ACK’s cooler, more rugged younger brother who wears Patagonia instead of Vineyard Vines.
Entry: $829,000, 3 bd 2 ba, 2,196 sqft (San Juan Island)
CATALINA ISLAND, CA
Typical: $1,830,000, 2 bd 2 ba, 2,801 sqft
The Time Machine
Imagine if Nantucket was located 22 miles off the coast of Los Angeles and had a Mediterranean fever dream.
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The Vibe: Avalon is the only town here, and it looks like a tiered Italian village that got lost. Like Mackinac, cars are strictly limited; most people get around in Autoettes (glorified golf carts).
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The Conservation: About 88% of the island is owned by the Catalina Island Conservancy. You aren't just buying a house; you’re buying a tiny slice of a nature preserve that happens to have a casino (the ballroom kind, not the gambling kind).
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The Cost: Inventory is incredibly tight. Small condos start around $800K, but a proper house with a view of the harbor will run you $2M to $6M.
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The Verdict: It’s the Hollywood version of Nantucket — more dramatic, more vertical, and you might see a bison (yes, actual bison) on your morning hike.
Entry: $949,000, 3 bd 3 ba, 1,645 sqft
OCRACOCKE ISLAND, NC
Typical: $785,000, 3 bd 2 ba, 1,120 sqft
Entry: $525,000, 3 bd 1 ba, 1,100 sqft
The Southern Outpost
Located at the tail end of the Outer Banks, this is the island for the person who truly wants to disappear.
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The Vibe: Accessible only by boat, this is the end of the world in the best way possible. It’s a 16-mile sandbar where the village is tucked into one corner and the rest is just wind, sea oats, and wild ponies. People get around by golf cart, and dressing up means putting on shoes.
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The Conservation: The entire island, save for the village, is part of the Cape Hatteras National Seashore. It’s federally protected, meaning your backyard is guaranteed to remain a pristine, undeveloped dunescape forever.
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The Cost: Real-world prices for an out-of-this-world location. You can find typical island homes for $600K to $900K.
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The Verdict: It’s Nantucket stripped of its wallet. On Ocracoke, status is measured by how long you can stay disconnected from the grid, not the square footage of your shingle-style cottage.
VINALHAVEN, ME
Prime: $1,250,000 4 bd 2 ba, 2,430 sqft
Entry: $365,000, 4 bd 2 ba, 2,430 sqft
Grit and Granite
If Nantucket’s a polished mahogany yacht, Vinalhaven is a 40-foot lobster boat, heavy, honest, and built for work. It’s where the charm isn’t curated but forged by the North Atlantic.
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The Vibe: This is a working island first and a summer retreat second. While Nantucket’s heart beats for the seasonal tourist, Vinalhaven’s pulse is one of the most productive lobster fleets in the world.cIt’s rugged, unpretentious, and completely indifferent to your status.
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The Nantucket Factor: You trade the high-speed catamaran for a 75-minute industrial ferry from Rockland, and swap sandy bike paths for deep, water-filled granite quarries that serve as swimming holes. Instead of rose-covered cottages, you’ll find weather-beaten Victorians and sturdy farmhouses built to survive a Maine winter.
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The Cost: $400K gets you a village house. $4M buys a sprawling deep-water estate. You get world-class waterfront privacy for a fraction of the price, provided you don't mind a little bait-smell on the breeze.
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The Verdict: A great escape for the Nantucket veteran who loves isolation without the country club performance.
ST. CROIX, USVI
Typical: $699,000, 2 bd 2 ba, 1,250 sqft
The Real World Alternative
If Nantucket is a curated museum, St. Croix is a working town that happens to be surrounded by turquoise water.
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The Vibe: It’s larger, scrappier, and significantly more diverse. It’s where you go when you realize that curated scarcity is just another way of saying "I can’t find a plumber."
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The Conservation: Between the Sandy Point Wildlife Refuge and the East End Marine Park, the island is a fortress for leatherbacks and coral. It’s rugged, protected, and keeps the high-rises away.
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The Cost: You can grab a condo for $150K or a serious estate for $1.5M.
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The Verdict: It’s the off-ramp for the Nantucket dream. You get the island life without the performance art of being a Nantucketer.
Entry: $290,000, 3 bd 2 ba, 1,554 sqft
The Mendoza Line
People don’t leave Nantucket because they’ve fallen out of love with the island. They leave because the math no longer works. When you combine an impossible housing market with the skyrocketing cost of daily essentials, the island stops being a home and starts feeling like a place where survival is the only full-time job.
Every island on this list offers a version of the Nantucket dream, but they all lack one thing: The ghost of whaling past. You can buy a beach in Florida, but you can’t buy the feeling of 300 years of isolation baked into the cobbles of Main Street.
If you move, you’ll save money. You’ll in many cases be warmer. But every time you see a Jeep with a 02554 sticker in the wild, you’ll feel that little tug.
My advice? Go to St. John. If you’re going to leave the best island in the world, you might as well do it in a place where you can wear flip-flops to the grocery store without someone judging your brand choice.
