Cape Cod, Nantucket & Martha's Vineyard

By:  Jennifer Milano, written October 2015, updated July 2016

As much as I love traveling any time of the year, at the height of summer there's almost no place I'd rather be than other than eating a hot, buttered lobster roll on the Cape, cycling along a path on the way to the beach on Nantucket, or licking an ice-cream cone from Mad Martha's on the Vineyard.  New England summers are bliss (when the weather cooperates).  Here are some of my favorite spots in this treasured part of New England:

Cape Cod:

How to get here:  Drive.  You will want your car.  If you can fit your bikes on the back or roof of your vehicle, do so.  The Cape Cod Rail Trail is a fun, traffic-free place to cycle.

Where to stay:  Every New Englander has his or her favorite spot on the Cape.  Mine is Chatham, because I grew up visiting my uncle and cousins there, and my parents found the Chatham Bars Inn.  My memories of the Inn from the 70's and 80's are akin "Dirty Dancing."  Not the dirty dancing part, but staying in the cottage-style rooms, dancing with my dad after dinner in the main dining room, and taking part in the Inn's group activities.  These days the Inn is more of a resort - a very, very expensive resort.  Except for the price, it is a wonderful family vacation spot.  Clambakes and games for the kids on the beach, a zero-entry pool and cannonball competitions, a boat launch to take you past seals swimming in the sea to outer beaches, and a kids' club that my children beg to return to each year.  A fifteen-minute walk will take you to Chatham's adorable town center, or the Inn will drive you, free of charge.  Note that the three-night minimum in summer becomes a four-night minimum around the second week of July.  If the high price tag forces you to stay elsewhere, consider booking a clambake dinner at the Inn.

Where to eat:  Whether or not you are staying at the Chatham Bars Inn, the Monday-Thursday evening clambakes are lots of fun, and lunches at The Beach House are generally good and afford great views from the deck.  We also like the Sacred Cod Tavern in the main inn, and my kids talk about the hotel's breakfast buffet all year long.  If price is no object, eat at the main dining room at CBI, called STARS.  The food was farm-fresh and delicious.  Ask for a table by the window for an ocean view.  Outside of the hotel, we used to like to eat at the Wild Goose Tavern at the Wayside Inn in the center of town, but this past year the food was not good. We've liked our meals at Pate's or at the fish pier.  The Chatham Penny Candy Shop in town is also an annual highlight, where Grandpa likes to hand an empty bag to each grandchild and watch their delighted faces as they fill the bags with more candy than their parents would ever let them eat.  Emack & Bolio's has our favorite ice-cream in town.

What to do:  As long as the sun is shining, the Cape epitomizes summer fun.  Orleans has beautiful beaches, the Cape Cod Rail Trail offers traffic-free cycling, you can play tennis, water sports, and mini-golf.  There are bumper boats and a trampoline park in Harwich Port.  On summer Friday evenings, a live band entertains locals and vacationers at Kate Gould Park in Chatham, beginning at 8:00 pm.  The fish pier in Chatham is fun - you can watch the fishing boats unload their daily catch, and the seals hoping for scraps.  If you are, or have, sports fans, you can catch a free baseball game by the Chatham Anglers.  On a cloudy day, you can shop in town or travel to Hyannis or Provincetown for more action.

Nantucket:

How to get here:  Unless you have a yacht, your choices for arrival are airplane or ferry.  Cape Air/Nantucket Airlines and Island Air operate flights to Nantucket from Boston, Providence, Westchester (NY), Hyannis, New Bedford and Martha's Vineyard.  Ferries run from Hyannis on Cape Cod, with the fast ferry (no vehicles) taking only an hour.  It is expensive to get your car over to the island, and if you are going for just a few days you don't really need one.  You can explore the island on its bike paths, take a taxi to your destination, or rent a car for the day on the island.  If you are island-hopping, ferries run between Martha's Vineyard and Nantucket.

Where to stay:  My husband and I secured an off-season, mid-week reasonable rate at The Nantucket Hotel & Resort, and we loved everything about the hotel (except for the lack of a warm welcome by the desk clerk on duty when we arrived).  Our suite was spacious and well-appointed.  The hotel was quiet, yet only a ten-minute walk to town.  The hotel provides beach shuttle service, and has two swimming pools.  We have wanted to return with our kids, but summer rates are exorbitant.  If you want to be in town, there are several bed and breakfasts that offer more affordable options.  For week long stays in summer, go for a house rental (with an outdoor shower!).

Where to eat:  Unlike other New England islands like Block, Nantucket is home to many high-end restaurants with inventive and outstanding food.  Our dinners at American Seasons and Straight Wharf were both incredible.  If we had stayed a third night, we would have tried Company of the Cauldron. 

What to do:  We rented bikes in town and spent the day riding past cranberry bogs to Madaket, a tiny town with a beautiful beach in the southwestern part of the island.  Nobadeer Beach was my favorite spot as a teenager, but not the ideal beach for families as the waves are huge and there are no facilities.  The Nantucket Hotel & Resort shuttles young families to the calm Jetties Beach, and teenagers and thrill-seekers to Surfside Beach.  Walking around the cobblestone streets in downtown is like stepping back in time. 

Martha's Vineyard:

How to get here:  Cape Air/Nantucket Airlines flies from Westchester (NY), Boston, New Bedford, Providence and Hyannis to the Vineyard.  There are several ferry options.  If you are bringing a vehicle, take the 45-minute ferry ride from Woods Hole on Cape Cod to Vineyard Haven, and book many months in advance.  If you are leaving your car behind, passenger ferries run from Falmouth and Hyannis on the Cape, as well as New Bedford, Massachusetts and Quonset Point, Rhode Island (the latter taking a mere hour and a half, and you avoid Cape traffic!).  Make sure you check into which town your ferry arrives on the Vineyard, and choose the one closest to your accommodations if you have no car. 

Where to stay:  There are three main towns on the Vineyard:  Edgartown, Vineyard Haven, and Oak Bluffs.  Edgartown is known as the most upscale town, filled with gorgeous, stately homes, beautiful shops and nice restaurants.  While not as upscale as Edgartown, I prefer Vineyard Haven, with its cute main street and more authentic feel.  Oak Bluffs is home to historic gingerbread houses, and also a carousel for the little ones.  I love the area known as East Chop, which is along the water between Oak Bluffs and Vineyard Haven.  While the area is residential, cycling by beautiful shingle-style homes along the seaside road is one of my favorite things to do on the island.  We have rented homes in Oak Bluffs, and loved it because the houses had porches with ocean views, yet we could walk to town for lunch or ice cream.  The downsides were that we needed to drive to the beach, and in the height of summer the lack of air-conditioning meant the houses were hot - too hot to sleep well. 

Where to eat:  The island's two most famous eateries are Mad Martha's for ice-cream and The Black Dog Bakery & Café, which has opened up retail shops all over New England in recent years. We loved Slice of Life in Oak Bluffs for a casual lunch (the restaurant also serves breakfast and dinner). For a more upscale meal, try Sweet Life in Oak Bluffs.  If you are cooking, visit one of the Vineyard's many farms or farmers' markets for fresh, island-grown ingredients!  Click here for a 2015 article in Martha's Vineyard Magazine on the best food in Martha's Vineyard

What to do:  The Vineyard has been a great summer vacation destination for my family, especially when my kids were really young.  We've rented some lovely houses with views of the water, although the last time it was so hot in our non-air-conditioned bedrooms up in the attic that we have taken a break from summer rentals on the island, where most of the homes rely on "ocean breezes" to cool their interiors (even when the homes are nowhere near the ocean). 

We spend our Vineyard days going to the beach, walking to Mad Martha's for ice cream, cycling the many bike paths on the island and sitting outdoors enjoying the view.  Joseph Sylvia State Beach stretches for two miles between Oak Bluffs and Edgartown, and its clear, calm water is especially good for kids.  On the wilder side, try Katama Beach on the south side of the island, which has big waves.  When our daughter was three, she loved the programs run by Mass Audubon for families.  Her favorite was walking through the woods to the beach, where she and other children collected creatures from the sea.  After gently depositing shrimp, crabs and fish into kiddie pools, staff taught the children about what they had discovered in the water.  Click here for more information.  She also loved riding on the Flying Horses Carousel in Oak Bluffs.

What to read:  "Caleb's Crossing," by Geraldine Brooks is a novel set in Martha's Vineyard in the 1600's, and will give you an appreciation for the island's history.