The Islands of New England: A local’s Guide to Coastal Charm
There’s something deliciously nostalgic about summering on a New England island. Whether you arrive barefoot on a ferry or in linen on a puddle-jumper plane, each island has its own rhythm — a distinct cocktail of salt air, sailboats, clam shacks, and sea-glass elegance. The roads are slower, the seafood fresher, and time? It moves more like a tide than a ticking clock.
Let’s explore four of my favorite New England island escapes — from the polished porches of Nantucket to the rugged edges of Block Island — with travel tips, signature stays, and story-rich suggestions for every kind of traveler.
Martha’s Vineyard
Wicker baskets, Kennedy legends, salty bicycles, and sunset clambakes.
Why Go
Martha’s Vineyard blends rustic beach town charm with old money ease. You’ll find quaint gingerbread houses in Oak Bluffs, boutiques and harborfront dining in Edgartown, and up-island farms and lighthouses that feel like New England’s wild soul still breathes here. A perfect island for families, creatives, and romantics who want their oysters served with a side of poetry.
Where to Stay: Harbor View Hotel
Located in Edgartown with sweeping views of the lighthouse, this historic hotel offers timeless Vineyard charm with contemporary comforts. Think expansive porches, sailboat-watching over morning coffee, and luxury suites that whisper old-world romance. It’s polished without being pretentious — a favorite for milestone celebrations and peaceful resets alike.
Getting There
Cape Air from Boston, NYC & beyond
Ferries from Woods Hole, Falmouth, Hyannis
Private yacht or charter available upon request
Nantucket
Whale oil tycoon heritage with a modern coastal aesthetic. Come for the cobblestones, stay for the champagne.
Why Go
Nantucket is polished, picture-perfect, and undeniably charming. It’s for those who love their sand dunes with a splash of Veuve, their inns with 800-thread-count sheets, and their seafood towers with harbor views. Ideal for couples, honeymooners, and lovers of design, fashion, and a good sail.
Where to Stay: White Elephant Nantucket
This iconic harborfront resort offers understated luxury with a Nantucket soul. Sip rosé on your private terrace, indulge in a spa day with sea-inspired treatments, or cruise out on their private yacht. Bonus: their waterfront restaurant, Brant Point Grill, serves one of the island’s best lobster rolls.
Getting There
Cape Air / Tradewind Aviation
High-speed ferry from Hyannis
Helicopter charter for the ultra-refined arrival
Block Island
Wild, windswept, and wonderful — like the Rhode Island cousin who drinks mezcal and reads poetry on the beach.
Why Go
Block Island is off-the-radar in the best way. Windswept bluffs, tiny winding roads, and more mopeds than Teslas. It’s perfect for travelers who want something low-key, nature-forward, and totally unplugged — with just the right hint of whimsy.
Where to Stay: The Spring House Hotel
A historic stunner on a hill overlooking the sea, The Spring House delivers a peaceful perch with wraparound porches, Adirondack chairs, and the kind of golden light that begs for a good book and a Negroni. The farm-to-table restaurant is a standout, as is the ability to truly disconnect.
Getting There
Ferries from Point Judith, Newport, or New London
New England Airlines (a 12-minute flight from Westerly, RI!)
Private boat/yacht charters available
Star Island
Where the sea meets story — a time-traveling retreat wrapped in salt air and granite charm.
Why Go
If you grew up on the New Hampshire seacoast, you know the magic of Star Island. It’s not flashy or fussy — but it’s got something better: soul. Accessible only by boat, this tiny island is part of the Isles of Shoals and feels like a dream caught between a children’s adventure novel and a 19th-century seafaring journal. Days unfold slowly here — think tidepool walks, porch rocking, garden wandering, and conversations that stretch long after the sun sinks into the Atlantic.
This is for seekers, creatives, and nostalgia-lovers. The kind of travelers who don’t need marble bathrooms or room service, but crave presence, quiet beauty, and that rare feeling of truly being off the grid.
Where to Stay: The Oceanic House (Star Island Conference Center)
The historic Oceanic House isn’t a luxury resort — it’s something better for the right traveler: a portal. Stay here and you’ll sleep where artists, philosophers, and writers have since the late 1800s. The rooms are simple, the porches are deep, and the views stretch into forever. Star Island hosts seasonal themed conferences ranging from art and ecology to mindfulness and interfaith dialogue — you can participate, or simply soak up the serenity. Yes, there’s a snack bar (bless it). And yes, swimming off the rocky coast is a rite of passage.
Getting There
Ferry from Portsmouth, NH via the Isles of Shoals Steamship Company
Private boat or water taxi options available
Add-on to a Portsmouth or coastal New England trip — a perfect spiritual interlude
✨ Add Star to Your Story
For those looking to escape the algorithm, reconnect to wonder, and fall asleep to the hush of ocean waves through open windows, Star Island offers an experience that’s profoundly simple — and simply profound.
Let’s plan a retreat with soul, salt, and stories you'll carry long after you leave.
✈ Bonus Tip: Getting Around
Cape Air is your go-to for small plane flights to the Vineyard, Nantucket, and more — think first-class charm without the TSA line. I also partner with private jet and helicopter charters for bespoke island-hopping escapes, as well as yacht rentals for those wanting to make waves between landings.
💙 Say Y.E.S. to the Islands
Each of these islands offers a different flavor of New England coastal life — from chic and celebratory to quiet and contemplative. Whether you're craving a romantic long weekend, a multi-generational summer adventure, or simply a fresh breeze and fresh oysters, I’ll help you craft an escape that feels just right.
Let’s design your story — one sandy footprint, chilled glass, and sea breeze at a time.
Because some places aren’t just visited — they’re felt.