• Wednesday, September 30, 2020

Summer in Massachusetts

Massachusetts – All-American Summer
August 21, 2013
By , Founder and Editor-in-chief

White clapboard houses. Golden retrievers bounding across manicured lawns. Obscenely attractive families with blindingly white teeth. No, this is not a Ralph Lauren campaign. This is real life. At least in Cape Cod, Nantucket, and Martha’s Vineyard – three quintessential American summer destinations.

These little blue-blooded islands off the coast of Massachusetts are widely known for their country club etiquette and resolute acceptance of madras plaid. After all, the Kennedys were practically an institution on Cape Cod, and it’s very possible that Nantucket is keeping the white wine spritzer alive. It’s a storybook WASP existence, and we can’t get enough of it.

So pack your Hilfiger-clad family into your Land Rover and head out for a weekend of old-fashioned American fun, including coastal bike rides, clambakes, and Chardonnay by sunset. Just in time for Labor Day, the secret about these destinations is that they’re even better from September to however long the Indian summer lasts.

Cape Cod

Think of Cape Cod as your gateway to Americana. It’s the easiest (relatively) to get to without flying, and the most simple of the three destinations. If you base yourself in Cape Cod, plan to take the ferries to Nantucket and Martha’s Vineyard for day trips. 

How to get there: You will want a car on Cape Cod to fully explore, though if you’re driving from NYC or anywhere not within a few hours’ car ride, you’re better off flying into Boston and then renting a car. For the ferry to Cape Cod: Make sure you have a reservation for yourself and especially for your car if you’re planning to take the car ferry to Provincetown in high season. If someone else is dealing with the car logistics, you can take a passenger ferry from Boston to Provincetown in about 1.5 hours.

Where to stay: Ocean Edge, a classic hotel whose mansion rooms have been completely renovated to provide some of the most luxe accommodations, without breaking the bank, in Cape Cod. Think private beach and top service, in a locale central to exploring the Cape. 

What to do: Besides gorging on lobster rolls for your entire stay, get active and hit the links – these are the best golf courses in the area, and Ocean Edge has its own $8.5 million Nicklaus-designed course. Charter a boat to sail for the day, making sure to include other refined activities of tennis and croquet, and you have yourself an East Coast vacation.

Where to eat: For high-brow meals, head to Abba and the Bramble Inn, which have some of the finest food on the Cape. For those who prefer to dine with lobster bibs and no tablecloths, swing by the quintessential no-frills seafood shack, Lobster Claw, for a fresh boiled lobster with plenty of drawn butter. Go on a tour de lobster roll of the Cape to judge for yourself who makes the best, from the Raw Bar in Mashpee to the Lobster Pot in popular Provincetown.


Quintessential Americana – this is what the Tommy Hilfiger marketing dreams are made of. Nantucket has something for everyone, and is arguably one of Massachusetts' best for all-around hotels, restaurants, shopping, and activities.

How to get there: Private plane, of course. Or close to private – Tradewind Aviation has a scheduled charter that runs from Teterboro to Nantucket frequently during the summer months. Otherwise, Delta and Jet Blue will charge exorbitant prices for the short flights from East Coast cities like NYC. If you are bringing a car onto Nantucket, it’s expensive – around $500 for the ferry reservation. Otherwise, the island is bike-friendly, so plan to bring your own or rent one when you arrive. 

Where to stay: If you’re not renting a house with friends, the top hotels are the Wauwinet and White Elephant. It’s top dollar, but that’s the cost for your perfect slice of Americana. Beautiful Places rents fully serviced villas – think private chef, full staff, and housekeeping. Definitely the way to roll. 

What to do: Hit the beach, kick back, and relax. Also, explore towns like Siasconcet, with its beautiful homes, and stop for dinner at the Summer House. Plan to get lost in the alleys and shops of the main town, while refueling over beverages and seafood apps along the way. Also, picnic at the Oldest House for a leisurely afternoon. 

Where to eat: Nantucket has the best food scene among the three destinations, with Queequeg’s, Straight Wharf, Corazón Del Mar, and Boarding House as top choices. For takeaway and casual meals, stop by Petticoat Row Bakery, Provisions, and Something Natural

Where to drink: For an old-school dive experience, grab a pint at Brotherhood of Thieves. Slip 14 and Boarding House are more grown-up scenes.

Martha’s Vineyard

Rustic, relatively unspoiled, and exclusive enough for everyone from Jackie Onassis to the First Family, Martha’s Vineyard is as laid back as American aristocracy gets. Plan to rent a compound, shuttle in your entourage, and entertain at home for the week. 

How to get there: Book a flight through Jet Blue, Cape Air, or Delta, and fly direct. To go through Boston and then drive is not recommended. In NYC, there’s a ferry you can take directly from Manhattan. One you’re on the island, plan to bike everywhere or take the expensive taxis. Or, with advance planning, rent a jeep for the group. 

Where to stay: Renting a house is the best option. You can find beachfront rentals via VRBO and HomeAway, which both have healthy selections. If you’re traveling sans entourage, Harbor View Hotel is a gorgeous boutique option.

What to do: Martha’s Vineyard is known for its beaches, so plan to spend some serious time exploring the surf beaches of Aquinnah and the lively sands of Edgartown.

Where to eat: Besides cooking up big lobster feasts at home with friends, Edgartown has the most happening restaurant scene. Check out Lucky Hank’s and Martha’s Vineyard Chowder Company. The best bet, though, is to find your local fish store and buy lobsters that were just plucked from the ocean that day. For dessert, indulge in the ricotta panna cotta at Sweet Life Café. Out here, it’s a sweet life indeed.