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New York, NY

We are parents, too. We think traveling well and traveling with children shouldn’t be mutually exclusive. We have limited vacation time, and we’re not spending our few days of freedom in lousy hotels eating bad food. We know the world is full of wonderful resorts, cool urban escapes and far-flung lodges that can make our time with our kids count. We want it all, and we don’t think it should be so hard to find. So we’re going to share it with you.


Martha's Vineyard Summer Guide for Families

Travel Journal

Travel Journal

Dispatches from around the world

Martha's Vineyard Summer Guide for Families

Henley Vazquez

Summer is around the corner. Seriously, we can almost feel it! The island retreat of choice for relaxed New Englanders and preppy summer sailors, is Martha's Vineyard and it also happens to be the topic of our newest guide. We love the quaint cottages and family-friendly hotels, in addition to the casual bistros, and of course, the lobster rolls. You can read on to explore some of the highlights of new Martha's Vineyard guide.

Getting There

By Air

Commercial airlines such as Jetblue, Delta, Cape Air and American run seasonal flights from major East Coast cities; for those who want something more posh, check out Tradewind Aviation, which offers scheduled as well as private charters. The small runway is frequently fogged in, so prepare for delays.

By Sea

Summer visitors take note: the car ferries book up ages in advance, so if planning to visit and bringing your own car, plan ahead. Like now. Otherwise you might find yourself traveling at odd hours or stuck without a car on the island (bad news, as a set of wheels is essential). Passenger ferries tend to be more flexible, but don't tempt fate, eh?


  • South Beach is one of the island’s best, and Winnetu guests have it just steps from their front door.
  • Don’t sweat your sassy teen who swears she’s totally over the family vacay; unlike hotels that focus entirely on the under-10 set, Winnetu has a teen adventure program that takes kids mountain biking, kayaking and even launching themselves off the famous bridge.
  • Families of five, who are often forced to book two rooms or an expensive suite, will appreciate the clever design of Winnetu’s rooms; one-bed suites have a sofa bed plus a fold-down twin bed to easily sleep three kids.


  • Considered by many the most family focused of the Vineyard resorts, the sprawling Winnetu wins repeat visits with its beachfront location, kid-friendly attitude and wide variation of suites and cottages that fit just about any family and a variety of budgets.
  • Martha’s Vineyard isn’t the kind of place to stay put in a hotel, but if there’s a place to do it, it’s Winnetu; with tennis courts, a fitness center, yoga classes, two heated swimming pools and a beach, the activity choices are a step above the island norms.
  • The 134 rooms have a variety of layouts and views, but all feature fresh, beach-inspired decor, kitchenettes and private patios from the garden studio level and up.



  • There’s only one restaurant, and eating repeated meals there can get boring, but Edgartown’s restaurants are a short drive from the resort.
  • Don’t expect a sexy infinity-edge swimming pool; the pools are heated and even have water jets for kids to play in, but they aren’t cutting-edge design.
  • Not all suites have doors dividing the living room and master bedroom, so if you want to play the tv without wearing headphones, choose carefully.


  • Studio rooms have a queen bed, a day bed for one child and kitchenette; for families with just one child, these are cozy but cute and sleep everyone comfortably on real beds.
  • For couples with sharp elbows who require a king bed, don’t go smaller than a garden studio, and a one-bedroom suite is better if traveling with kids.
  • Larger accommodations include cottages as well as townhouses and private homes.


Chesca's Restaurant
38 N Water St, Edgartown
+1 508-627-1234

The island’s go-to trattoria satisfy’s the lobster roll craving with lobster ravioli and lobster risotto, plus some good grilled fish and meat for those who are carb counting. Good with the kids or without.

State Road
State Rd, West Tisbury

Book a babysitter for a night out at West Tisbury’s only fine dining establishment, but keep in mind that even this more sophisticated eatery is far from formal and has a burger night when regulars roll up their sleeves to dig into patty melts and kielbasa. Take note of the decor: it was done by Michael Smith, aka the guy behind the Obama White House design.


South Beach
Herring Creek Rd, Edgartown, MA

No, not Miami. This three-mile beach is one of New England favorites, but remember that this is the Atlantic side of the island, so keep an eye on kids who aren’t strong swimmers as the surf can be powerful. The bike path from Edgartown is the easiest way to reach if you aren’t driving.

Island Alpaca Company
1 Head of the Pond Rd, Vineyard Haven, MA

Visit these furry creatures at their farm outside of Vineyard Haven. Although teens probably won’t be impressed, younger kids will get a kick out of them—and the babies are adorable.

Martha's Vineyard Bike Rentals
1 Main St, Edgartown, MA
1 800-627-2763 

Well-paved paths crisscross the island, and exploring on two wheels is one of the best ways to see Martha’s Vineyard (and burn off all those lobster rolls). Every town has at least one bike rental company, and they also offer burleys and children’s bikes for families.

Cover image via

Images via Winnetu