Martha’s Vineyard vs. Nantucket? Do Both.
Most travelers spend weeks debating Martha’s Vineyard vs. Nantucket.
Which is better?
Which is more charming?
Which is “worth it”?
The reality?
The best way to experience them isn’t to choose….it’s to do both, and to do it well.
Through my relationship with the Little Gem Resorts collection, I design a seamless two-island itinerary that connects Winnetu Oceanside Resort on Martha’s Vineyard with The Nantucket Hotel & Resort, turning what feels logistically complicated into something completely effortless.
This isn’t just two hotel stays. It’s a fully coordinated, multi-island New England summer experience.
If you don’t have your summer plans booked, it’s time to make plans now, since space is filling up. If you’re reconsidering abroad and staying closer to home, this is the answer, especially East Coasters.
The Insider Way to Do Both Islands
The Two-Island Adventure by Little Gem Resorts connects their two signature properties:
Winnetu Oceanside Resort (Martha’s Vineyard)
The Nantucket Hotel & Resort (Nantucket)
They coordinate:
Ferry logistics between islands
Transfers and timing
The overall flow of your stay
Which—if you’ve ever tried to plan both islands yourself—is exactly where things get complicated.
This is the easiest way to experience Martha’s Vineyard and Nantucket in one trip—without sacrificing style or sanity.
Stop One: Martha’s Vineyard (Winnetu Oceanside Resort)
Start your trip on Martha’s Vineyard, where the pace is slower, softer, and more expansive.
At Winnetu, you’re set along South Beach with a private path to the ocean—one of the most coveted stretches of coastline on the island.
This is your barefoot luxury chapter:
Long beach days and bike rides
Clambakes and golden hour dinners
Easy access to Edgartown’s harbor charm
A relaxed, family-friendly energy
Martha’s Vineyard feels like summer camp…. if summer camp had impeccable taste.
The Transition (Where This Trip Wins)
This is where most travelers get stuck.
Ferry schedules. Timing. Transfers. Luggage.
With Little Gem Resorts, it’s all handled for you.
The ferry between islands takes about an hour, and your entire transition is coordinated in advance.
The difference between a good trip and a great one here isn’t just the destination—it’s how seamlessly you move between them.
Stop Two: Nantucket (The Nantucket Hotel & Resort)
Then you arrive in Nantucket—and everything shifts.
More polished. More social. More cinematic.
At The Nantucket Hotel, you’re steps from downtown and Brant Point, with easy access to everything that makes Nantucket iconic.
This is your refined summer chapter:
Morning coffee walks into town
Boutique shopping and harbor views
Beach afternoons followed by cocktails
Classic New England elegance at every turn
If Martha’s Vineyard is relaxed nostalgia, Nantucket is storybook perfection.
Martha’s Vineyard vs. Nantucket: The Truth
They’re not interchangeable.
They’re complementary.
Martha’s Vineyard: laid-back, expansive, beach-driven
Nantucket: polished, walkable, socially vibrant
The magic is in the contrast and experiencing both is what makes this trip unforgettable.
What This Trip Actually Costs
This isn’t a budget beach trip; it’s a quintessential New England summer done right.
What You’re Paying For:
A coordinated two-island itinerary
Ferry and transfer logistics
Two high-end coastal resorts
Peak-season New England travel
Realistic Investment (Per Couple)
Travel Style Total Trip (4–6 nights)
Shoulder Season (May-June / Sept-Oct) $4,000 – $6,500
Peak Summer (July–Aug) $6,500 – $12,000+Premium (suites / cottages) more like $12,000 – $20,000+
The Advantage of Booking Through a Travel Advisor
You can absolutely book these hotels online.
But you won’t necessarily get the same experience.
Through my access, including preferred partner relationships and perks, I’m often able to offer:
Room upgrades (when available)
Daily breakfast for two
Resort or experience credits
Priority for early check-in / late check-out
Preferred room placement
And beyond perks:
It’s about how the entire experience is designed from which island you start on, to how your stay flows, to making sure you’re in the right room category for your trip.
Who This Trip Is For
First-time Nantucket + Vineyard travelers
Couples wanting a cinematic summer escape
Families who want ease + structure
Travelers who value experience over logistics
Who It’s Not For
Quick weekend trips
Budget-focused travelers
DIY planners who prefer to build everything themselves
The Takeaway
This is the kind of trip that feels like a memory while you’re still in it.
Hydrangeas spilling over white fences.
Bike rides to the beach.
Salt air at sunset.
It’s not just about where you stay.
It’s about how it all flows together.
Ready to Plan Your Two-Island Summer?
If you’re considering Martha’s Vineyard or Nantucket this summer, I’ll help you decide if doing both and doing it right is worth it for you.
Don’t delay since this summer is already upon us. Let’s start comparing dates rates, availability, and potential perks.
