Travel Guide | Martha’s Vineyard
A New England Dream: Our Memorial Day Weekend Getaway to Martha's Vineyard
We've had a summertime New England holiday on my travel wish list for years—think breezy sailboats bobbing in the harbor, weathered cedar shingles, rosé-filled afternoons, and that crisp, salty air that just begs for cotton layers and linen. As a devoted Elin Hilderbrand reader, Nantucket was my North Star. But one night this past Christmastime, while casually scrolling the Amex Travel Fine Hotels + Resorts portal (as one does), a perfectly targeted ad for the Harbor View Hotel in Martha’s Vineyard stopped me in my tracks. It had been years since Carter and I took a vacation just us two that was not associated with a friend's wedding weekend, and I was immediately enchanted by how romantic, historic, and charming - while still luxurious - the setting seemed. Just a few clicks later, plans were pivoted and bags were packed. Sorry, Nantucket—your time will come. But this trip belonged to the Vineyard.When to Go
Late spring through early fall is peak Vineyard season, but we discovered that Memorial Day weekend truly is an insider’s sweet spot. The island is officially awake—shops stocked, restaurants humming—but still deliciously quiet. The weather is that perfect blend of sunny and sweater-y, and with New England schools still in session, you get all the charm without the chaos. It’s like slipping into summer through a side door.A Beat in Boston
As a spoiler, my only critique of this destination is it is a bit of a hop, skip, and a jump to find your way there. However, rather than rush through a full day of travel, we made a mini-adventure out of the journey. We landed at Logan Airport, rented a car, and checked into our hotel—Hotel AKA Boston Common—which made for a stylish and centrally located home base. Since Carter had never been to Boston, we set off to explore Beacon Hill, starting with brunch and coffee at 75 Chestnut before diving into the literary wonderland that is Beacon Hill Books & Café. It felt like a little jewelry box of my book-loving heart’s desires.From there, we strolled through the Public Garden, soaking in the swan boats and spring blooms, then grabbed chic pre-ballgame cocktails at the gorgeous Contessa, high above the city. We enjoyed seven innings at the historic Fenway Park before capping off the night with fresh oysters and laid-back elegance at Union Oyster House. Then, it was time to turn in early for our coastal adventure.
Getting There
The next morning, we hit the road for Woods Hole, which is about a 90-minute drive from Boston. Once there, we parked and hopped on a short shuttle bus (say, 20 minutes) to the ferry terminal. The ferry ride to Martha’s Vineyard took about 45 minutes—I highly recommend purchasing your tickets online beforehand and having them ready in your digital wallet. After docking in Vineyard Haven, we took a taxi to Edgartown, our charming home base for the next few days. Where to Stay
We stayed at the iconic Harbor View Hotel, and it exceeded every hope I had for a sophisticated, boutique, and cozy New England stay. Perched perfectly by the water, with views of the Edgartown Harbor Lighthouse, it felt like we were on the set of a Nancy Meyers film. There’s a historic presence to the property that adds a rich sense of place (it was opened over 130 years ago) , and the service? Impeccable—from reception to concierge to waitstaff, everyone made us feel like old friends coming home. It was the kind of accommodation where the staff knows your name and you become friends with the other guests naturally. Thanks to our Amex Fine Hotels + Resorts booking, we were treated to a suite of dreamy perks: early check-in, late check-out, complimentary breakfast each morning (which was both elegant and satisfying), and a generous credit we happily used at the appointed hotel bar.The interiors were meticulously crafted: copper lantern fixtures, rich herringbone wallpaper, and the most striking glossy lacquered trim that made every hallway feel photo-worthy. We spent golden hour playing cards on the wraparound porch with drinks in hand, watching the lighthouse glow against the evening sky. And don’t even get me started on the pool—fizzy and fabulous with its peach and ivory stripes, fire pits flickering, and attended to by spectacular staff.
Our Itinerary
SUNDAY
After a smooth morning of travel, we arrived in Edgartown and made our way to the Harbor View Hotel, where we were greeted with warm hospitality and early check-in thanks to our Amex Fine Hotels + Resorts perks. We settled in, dropped our bags, and headed straight to the hotel’s wraparound porch for a deliciously unfussy lunch of sandwich fare with a side of harbor breeze. Post-lunch, we strolled across the street to the Edgartown Harbor Lighthouse and dipped our toes in the sand at Lighthouse Beach, taking in the natural terrain of our surroundings amidst the water and sand. 
Afterwards, we walked down Water Street, popping into a handful of local gems. The Vineyard Vines flagship store was perfection, and The Christina Gallery made my fine art-loving heart skip a beat—especially when I spotted a Duane Alt piece that made me melt. But the star of the afternoon? Nell—a contemporary women's boutique that was as charming as it was curated. The owner was an absolute delight, and her shop pup, Bosun, stole the show. I walked out with my new favorite cashmere sweater and a pair of perfect white jeans. Across the road, her sister store for home goods was equally dreamy.We slipped into Atlantic Fish & Chop House next and went full vacation decadence: champagne and caviar with a side of truffle fries. Indulgent? Completely. Worth it? Absolutely.
Bubbly and content, we grabbed a coffee from Toccopuro, then took the most glamorous 10-minute walk back to the hotel—passing some of the most stately and historic homes that line North Water Street. We freshened up and headed back into town for dinner at Alchemy, which was all dim lighting, cozy corners, elevated yet approachable dishes, and a spectacular wine list that had us lingering long past the last bite.MONDAY
We let ourselves sleep in after a cozy, firelit night playing Spades in the hotel lobby—exactly the kind of slow morning that makes a vacation feel like a true escape. Once we finally stirred, we made our way to Behind the Bookstore, a darling café tucked just behind Edgartown Books. With coffees in hand and a table full of light bites, we lingered in the garden before wandering into the bookstore itself. Carter picked out a Malcom Gladwell essay collection while I went straight for a mystery novel set right here on Martha’s Vineyard. Naturally.We meandered our way through downtown Edgartown after that, popping into little shops and stocking up on snacks and a few libations for later at Rosewater Wine & Spirits. The weather was perfect—sunny with a salty breeze, just a light sweater needed—and we let ourselves wander without agenda.
Eventually, we landed at The Seafood Shanty, perched above the harbor, where we fully leaned into island life: sipping cold beer, splitting a basket of fries, and playing cards for hours while watching sailboats drift by. It was the kind of carefree, sun-soaked afternoon that felt like a true summer escape personified.
A scoop of ice cream from The Ice Cream and Candy Bazaar was our next indulgence, because no seaside town day is complete without one. And, as we meandered back to the hotel, I stumbled upon Erica Wilson, the most darling needlepoint shop featuring a slew of bespoke canvases inspired by Martha's Vineyard.
Later, back at Harbor View Hotel, Carter slipped into a nap while I curled up on the porch with a light blanket and my new book. I watched the sun shift over the harbor, listening to the birds, the breeze, and the gentle lull of the day.
That evening brought the crown jewel of our trip: a private sunset sail with Catboat Charters. The beautifully restored Catboat was pure old-world charm with modern hospitality—Captain Alex made us feel instantly at home. We queued up my favorite yacht rock playlist, popped open some bubbles, and dug into delivery pizza from Edgartown Pizza (they have a fantastic gluten-free crust, by the way). As the sun sank into the water and the crisp evening wind filled the sails, we both agreed: this was one of the most magical experiences we’ve ever shared. If you find yourself on Martha’s Vineyard, book this charter.We disembarked around 9 p.m. and strolled back to the hotel for a nightcap, hearts full and hair full of salt air, already dreaming of returning.
TUESDAY
We woke up to our final morning on the island and headed downstairs to Bettini, the hotel’s signature restaurant, for breakfast. It was every bit as delicious as it was beautifully designed—think honey-toned wood, soaring skylights, and that breezy elegance that Martha’s Vineyard does so well. We lingered over coffee and eggs, soaking in the last bits of harbor light from our table.After breakfast, we took one last, unhurried stroll through Edgartown, letting ourselves get lost among the breathtaking homes and leafy streets that felt straight out of a coastal New England dream. It was the perfect farewell—a quiet goodbye to a place that already felt like a future tradition.Then, it was off to the ferry and back to reality, full of good wine, salt air, and so many stories to tell.
Next Time
We stayed exclusively local to Edgartown this time, soaking in all its postcard-perfect charm. But next time? We’re renting a Jeep and heading to Oak Bluffs and Aquinnah. Think colorful Gingerbread Cottages, cocktails at Donovan’s Reef, and sunset from the Cliffs. We’re also eager to take the little ferry across to Chappaquiddick for a day of exploring the serene, off-the-beaten-path side of the island. And while we loved our meals this trip, we already have our eye on a return to The Newes from America Pub—our Catboat Charter captain, Alex, highly recommended it as the perfect cozy local spot for a drink or bite, especially with a fire going on a chilly summer night. Sadly, it was closed on the Monday night we attempted to go in, but it’s at the top of our list for next time.If you’ve ever longed for a weekend that feels like a wistful, coastal novel come to life—rosé, romance, sea breeze, and all—Martha’s Vineyard is calling. Just don’t be surprised if you’re planning your return before the ferry even leaves the dock.