Cape Cod & The Islands Travel Planner

Nantucket, Martha’s Vineyard, and Cape Cod each embody the idyllic New England coastal summer in their own way—but what they all share is a deep-rooted clubbiness. These are places built on ritual and return visits: families who’ve been coming back for years, even generations, each with their fiercely gate-kept beach, go-to seafood shack, favorite bike route, and sacred sunset cocktail spot. For outsiders, cracking the code can feel daunting—from understanding the geography (the vibe shift between Up-Island and Down-Island on the Vineyard, or how the towns roll from Upper to Outer Cape), to getting in with the realtor who can hook you up with the best rentals a year in advance.

So we asked over 20 friends and insiders—people with houses across the Cape and Islands, or who have been making the pilgrimage for decades—to answer your (and our) questions and share everything they know (or at least are willing to part with—we had to pry!). We’ve got the lowdown on where to stay on Nantucket, from charming and almost-affordable to family- and dog-friendly, hunting for vintage treasures from old island estates, public golf courses and the best spot for provisions for your beach cooler. Where to stay on the Vineyard if you don’t have a car, the farmstands and markets worth the detour, and the island’s hidden lakes, best hiking trails, and most atmospheric seafood shacks. And then on the Cape: whether you’re drawn to the lively food and art scenes of Provincetown or the quiet village feel of Osterville. And across the whole wind-swept, grey-shingled coastal region, our insiders share the best beaches for swimming, surfing, and sunsets, plus rainy-day backup activities, and the ferry and traffic hacks that might just save your sanity.

Our Planner runs in this order: Nantucket, Martha’s Vineyard, then Cape Cod. And be sure to scroll down to the “Getting There & Around” section at the end for logistics!

CONTRIBUTORS

Alexa Brazilian is the coauthor of The Perfect on Substack and Contributing Editor at T Magazine. She has spent every summer of her life in Nantucket—her parents started coming in the ‘70s to their house in Codfish Park in ‘Sconset, a beachside community of tiny cod fisherman cottages. Today, she usually rents in Sconset for the week with her family. She says, “I love seeing my girls wild riding their bikes like I did as a kid. Nantucket has changed an awful lot since my youth, and doubly since my parents’ days. But if you just stick to long beach days and grilling at home after with family and friends, the spirit and beauty of the place is still alive and well.”

Carly Shea is a writer and the former lifestyle editor at Yolo Journal. She is a fourth-gen Masshole and has spent every summer of her life in some part of the Bay State.

Callie Stanton is the head of brand for Auberge Resorts, and has a home on Nantucket where she spends every summer.

Carlos Huber, originally from Mexico City, is the founder of Arquiste, a boutique fragrance brand that draws on his expertise in architectural history and inspiration from his global travels. He has been coming to Provincetown every summer and fall for over a decade. 

Cate La Farge Summers – Born and raised on Nantucket, she still spends summers on the island, now with her husband and two sons. She is at slow work on a book; meanwhile, her Substack features weekly pieces on motherhood, parenting a child with disabilities, her travels, and other reflections. 

Celine Yousefzadeh Laz is a culinary curator, the founder of CY Kitchen & CYK Caviar. Known for her meticulous eye and deeply intuitive approach to hospitality, Celine has become a leading voice in luxury hosting. 

Davlyn Mosley has been a Martha’s Vineyard regular for years, returning season after season. She authored a guide to MV for families with young children, and each summer finds herself enjoying the peaceful quiet of West Tisbury, where she was married in 2015. She lives in Los Angeles with her husband and young son. 

Drew Oliveira is principal of Two Louis, a Boston-based PR & communications firm serving independent hotels, resorts, and hospitality brands in New England and beyond. He’s spent 36 summers on Martha’s Vineyard and enjoyed a considerable amount of off-season time there. He’s a West Chopper, calling the community at the tip of that peninsula his home on the island. 

Eduardo Plaschinski is a veteran of the hospitality industry and cofounder of Niddo restaurants and cafés in Mexico City. His sister lives in Plymouth and he’s been visiting the Cape every year for nearly a decade.   

Eric Coles & Mark Chung are the grandsons of Lennox & Harvey, whose heritage, style and names inspired their concept shop, Lennox & Harvey—a reimagined local general store for the global, mindful, and design conscious. A block from the harbor in Vineyard Haven, the outpost offers an eclectic mix of purposeful goods for the home and body. They started coming to the Vineyard in 1995, when they rented a house with friends—and fell in love with the ease and the beaches, the farms and the sunsets. A decade ago, they bought a place and moved from NYC to this magical island that they love even more now, 30 years later.  

Eric Twardzik is a Boston-based freelance writer covering men’s style, food, spirits and travel, and the deputy editor at WM Brown magazine. He has made a number of visits to Martha’s Vineyard over the years, usually staying in Edgartown.

Erica Ashton is the executive director of the Martha’s Vineyard Chamber of Commerce. She  first came to the island at six years old, spending summers with family friends who rented in Katama. She used to cry every time they took the ferry home, and from a young age she knew she would find her way back to the Island full time as an adult.

Julia Blanter is the author of the newly published The Martha’s Vineyard Cookbook, a culinary adventurer and passionate home cook with extensive experience across the food industry. Born to Ukrainian parents in the colorful, multicultural landscape of Sydney, Australia, Julia has lived in the Netherlands, London, Brooklyn, and most recently, Martha’s Vineyard. 

Keija Minor is the former editor-in-chief of Brides at Condé Nast, with a passion for all things home-related. She now lives year-round in Oak Bluffs, MA, where as a real estate agent with Point B | Compass, she helps people find their dream home or rental on Martha’s Vineyard.

Kerry Carven – Content and communications by trade, sand and sunset-chaser by nature. She traded the east coast for southern California over a decade ago, and now lives in Ojai with her husband and three rowdy dogs. But the Cape is in her bones—her family lived there full-time in the early eighties before splitting between Osterville and the Boston suburbs—and she returns to visit her parents as often as possible. She says, “My sweet spot is early September, when the crowds thin out, the beaches empty, and the light does that special something that can’t be replicated.”

Kirstin Uhrenholdt is a chef and cookbook author who has worked “Up Island” in Menemsha, MV, for three decades. She says, “I am continually amazed by the discovery of new and beautiful areas of the island. It has been a delight to witness the growth, beauty, and flavor of the local farm and food movement. However, it has been challenging for the farmers to remain on the island. Therefore, please support them while you are here.” 

Liz Terry – A native of the Boston area, Liz has lived and worked in Washington, D.C. for the past two decades. (Still, her sports allegiances remain firmly in her Boston roots.) She spent her childhood summers in Brewster, and still gets back anytime she can. “If you look in the right areas,” she says, “you’ll find a solid, deeply rooted community—far away from the revolving door of summer tourists. Once you discover that, you won’t want to go anywhere else. ” 

Madeline Grayson is the co-founder of lifestyle retail brand Tuckernuck, which recently opened  A Sailor’s Valentine, a curated capsule store on Nantucket. After more than 30 summers on the island, Maddy considers Nantucket both her second home and a longtime source of inspiration.

Mary Goode is a Nantucket native and the founder of Nantucket Magic, a concierge, travel and event-planning company on the island. 

Meredith Hayden is a content creator, author, and founder of Wishbone Kitchen, a best-selling cookbook and a culinary lifestyle brand. Although well known for her years working as a chef in the Hamptons, she grew up visiting Nantucket with her family, and spent six summers working there. 

Meredith Hanson spent 12 years living on Nantucket and working as an artist before moving to Princeton, NJ with her husband. She still returns to the island throughout the year for custom collaborations—her whimsical, detail-driven work includes one-of-a-kind designs, architectural paintings, custom murals, and collaborations with local brands and businesses inspired by the places she loves most.

Peter Som is a fashion designer and cookbook author who has been going to Provincetown and the Outer Cape for decades. He is the author of Family Style: Elegant Everyday Recipes Inspired by Home and Heritage. Finding constant inspiration in his visits, he says. “Provincetown in particular has this magical mix of bohemian energy, incredible food, beautiful dunes, and total old-school summer nostalgia that keeps pulling me back.”

Ruthanne Gersten is a founding partner at Managed Solutions, a NYC-based brand marketing consultancy. She’s been going to MV for about 15 years, first renting a house with her family in Vineyard Haven, walking distance to town (“we had to go to free beaches since house rentals in VH do not come with any beach stickers”). After a few years, she settled on Up Island, in Chilmark. “It’s a quieter and less transient feeling. Even with grown kids now—we all still love it and go back every summer.”

Stephanie Madsen first came to Cape Cod in her 20s to work aboard a tall ship and later at Woods Hole Oceanographic Institution. She eventually returned to Falmouth, where she has lived year-round for the past 16 years. A geologist, sustainability advocate and lifelong lover of the outdoors, Stephanie loves sharing the everyday magic of the Upper Cape, be it walking a windswept beach, kayaking a quiet salt pond, biking the Shining Sea Bike Trail, hiking through the woods, or catching a sunset by the harbor.

Stephen Kent Johnson is an architectural and interiors photographer. He’s had a place with his boyfriend John Derian in Provincetown for 18 years. 

Stephen Orr is an author of several books and a former magazine editor at Better Homes & Gardens, Martha Stewart Living, Domino, Condé Nast Traveler, and House & Garden. A New Yorker for several decades, he and his husband bought an antique Cape Cod house in 2021 and now live near the tip of the Cape fulltime. His latest garden book, The Gardener’s Mindset: Connecting With Nature Through Plants was published by Clarkson Potter/Random House in May 2026. Also see his Substack, The Gardener’s Mindset.

NANTUCKET

Nantucket is a small, pork-chop-shaped island roughly 30 miles off the coast of Cape Cod, shaped by centuries of whaling history. Though it’s much more polished these days—you could throw a clamshell in any direction and hit a millionaire—life here still feels deeply elemental: fog rolls in thick and fast (hence the island’s nickname, the Grey Lady), hydrangeas grow to the size of small cars, and there’s not a single traffic light on the island, including in grey-shingled, cobblestoned Nantucket Town itself. 

STAYS

I’m planning our first trip as a family and we’re not sure if we should stay in town or further out. And should we do a hotel or rental?

If you’re not staying in town, you need to rent a car (expensive), or bring your car over on the ferry (be warned: getting a reservation for your car is like trying to get a table at Le Veau d’Or). Hotels I would recommend are The Wauwinnet (secluded, beautiful and quiet), The Cottages at Nantucket Boat Basin (full houses with kitchens right on the wharf in town), Greydon House (Roman and Williams-designed boutique hotel in town). Overall, it’s really nice to rent a house if you can. Securing something as early as possible is key. Don’t be afraid to start looking this summer for next summer! Hotels can be just as expensive in the high season and with a house you can grill dinner at home with fresh fish and farm corn and tomatoes after a long beautiful day at the beach. No babysitters or reservations (annoyingly, a near impossible task these days) required. Really the best way to enjoy Nantucket as a family. —Alexa Brazilian