How To Vacation On Martha’s Vineyard Like A Father-In-Chief

Stop complaining about the accents and start eating those lobestah rolls!

by Fatherly
Originally Published: 
martha's vineyard

Check out Fatherly’s complete 2016 summer vacation destination guide here.

For most New Englanders going to the beach means driving east for an hour or 2, opening a cooler of Sam Adams, switching on the Sawx, and slicing up their feet on a shoreline that’s more like sandpaper than sand. But, for the optimal East Coast seaside experience, you don’t need to stop at any Cape (be it Hatteras, Cod, or Ann). Instead, take a short trip on the Hy-Line over to Martha’s Vineyard, where you can treat yourself like a Kennedy for the week (or, even better, a Belushi). Yes, there is swimming, biking, sailing, and fishing galore. Yes, you’ll have a million lobster rolls. Yes, you’ll find yourself wearing salmon-colored pants — and you don’t even own salmon-colored pants! But, it might also be the best beach trip your family will take that doesn’t involve a passport.

All hotel and restaurant recommendations come care of the family travel experts at Passported; check out their full Martha’s Vineyard guide here.

Tips From A Local Dad

Vineyard Vines has been the signature outfitters of MV since 1998 (sorry Black Dog), and the 2 brothers who run it, Shep and Ian Murray, have explored every corner of the island with their kids. Here’s their list of what to do with yours, from Oak Bluffs to Chilmark.


Harbor View Hotel


  • Dating to 1891, this classic Vineyard resort sits 5 minutes walking from the village of Edgartown, offering families access to the best of beach and town; no car seat required.
  • The 114 rooms and suites are divided between historic buildings and individual cottages, and while the layouts and views vary, all have a classic New England look. Some rooms include 4-poster beds, plantation shutters, working fireplaces, and bay windows as well as private balconies.
  • Amenities include 3 restaurants, a pool and a gym, and there’s a beach across the street.


  • Suites vary, but the best for families have queen-sized sofa beds in the living room and kitchenettes.
  • The least expensive option for a family of 4 is a double queen room. There are only 4 of them in the main building, so plan ahead if you’re looking for an economical choice.
  • For extended families and major privacy, book one of the 2 or 3-bedroom cottages.


  • Within walking distance to Edgartown and its cute shops and restaurants.
  • Even in August, the Martha’s Vineyard ocean waters can be chilly, so having access to Harbor View’s heated pool is a major plus to parents whose temp preferences are more Carribean than North Atlantic.
  • During the summer season, complimentary kids’ activities include face painting, arts and crafts and lawn games.


  • While the nearby beach is fine for building sand castles, there’s no beach service and the water is a bit murky, so it’s better to travel to some of the area’s better swimming beaches.
  • The Governor Mayhew building is a standard hotel building and lacks the quaint historic details of the main building and cottages.
  • Bikes are the best way to get around the island, but the hotel doesn’t have them on-loan. The concierge can quickly connect you with a good bike shop in town to get your family outfitted.

House Rentals


  • Martha’s Vineyard has far more house rentals than year-round residents, and for larger groups traveling together, this is often the path taken for the sake of convenience and budget constraints.
  • For families looking for a creative way to finance a summer vacation, consider joining Love Home Swap and trade your regular apartment for a vacation house (the yearly subscription fee is less than booking one hotel room for a single night).
  • VRBO and Airbnb have a wider selection of houses available, in a variety of price ranges.


  • Space and privacy: for families who want to spread out, a house is the best way to go.
  • Most of the Vineyard’s hotels — with the exception of our favorite 2 — are small bed and breakfasts. They’re suited for couples but not for toddler. Houses welcome everyone.
  • Whether you want to be walking distance from the ferry in Vineyard Haven or hidden away in quiet Chappaquiddick, houses are everywhere, but hotels are not.

Winnetu Oceanside Resort


  • 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. It has tennis courts, a fitness center, yoga classes, 2 heated swimming pools, and a beach. The activity choices are a step above the island norms.
  • The 134 rooms are scattered throughout the low-slung building and have a variety of layouts and views. All feature beach-inspired decor, kitchenettes, and private patios from the garden studio level and up.


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


  • South Beach is one of the island’s best, and Winnetu guests have it just steps from their front door.
  • Don’t sweat your teen who swears they’re 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, kayakin, and even jumping off the famous bridge.
  • Families of 5, who are often forced to book 2 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 3 kids.


  • There’s only one restaurant and meals there can get boring, but Edgartown’s restaurants are a short drive from the resort.
  • Don’t expect a sexy infinity swimming pool; the pools are heated and 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 watch TV without wearing headphones, choose carefully.


Flickr / David Berkowitz

Date Night

The Sweet Life CaféWhite tablecloths and twinkling tea lights make Sweet Life’s patio a perfect pick for a romantic night out. The menu changes frequently based on what lands in local markets, but expect updated American classics like grilled local fish, roasted meats, and homemade pasta.

Lobster Rolls

Grace Church ParishThis Vineyard Haven church is widely considered to have the best lobster rolls on the island. Swing by early on Friday evenings in the summer to score a few for the family, then eat them down on the nearby Owen Park Beach.

Casual Lunch

Larsen’s Fish MarketThis tiny market buys from fisherman that dock at the back door and sells to residents who queue for the freshly-shucked oysters as well as chowder, sandwiches, and boiled lobster. BYOB and eat alfresco on the picnic tables outside the store. The adjacent beach is calm and safe for young children.

Home Port Restaurant


Art Cliff DinerOpen since the 1940s, this tiny diner is a popular breakfast joint. Expect a wait, but all the better to work up an appetite for the spicy chicken hash and chorizo and egg tacos. Look for their food truck for dinner takeaway.

Classic MV

Home Port RestaurantA Menemsha institution, Home Port does it all: Take away, eat in, kids’ menus, and a walk-up raw bar. What they don’t do is booze, so BYOB. They’ll even provide their own house-made mixers if you want to blend up your own cocktails.

All hotel and restaurant recommendations come care of the family travel experts at Passported; check out their full Martha’s Vineyard guide here.

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