Each week, Yahoo Travel pits writers from rival destinations against each other to determine once and for all which one is the best.
The Case for Nantucket - by Laura Begley Bloom
Nantucket is the Marilyn to Martha’s Vineyard’s Jackie (even though the Kennedys are over in Hyannis — but you get the point). The island has become a playground for the hyper-wealthy, with probably more billionaires per square mile than many other places on the planet. And even though the shingled gray “cottages” that give the island its nickname (The Little Grey Lady) may be charmingly discreet, people here aren’t afraid to flaunt their wealth. Note all the Gulfstreams parked at the airport. Set 30 miles off the coast of Massachusetts, this 14-mile-long island is a bit harder to reach than the Vineyard — and everyone here likes it that way. It is also smaller, with one main town and little settlements scattered about, like the rose-clad enclave of Siasconset (Sconset to locals). Now that summer has arrived, so have the multiple-home-owners who you’ll find in Aspen and Palm Beach the rest of the year.
Population: 10,000 year-round; 56,000 in summer
Famous Faces: Politicians like John Kerry; fashion designers like Tommy Hilfiger; and business tycoons like Jack Welch, former CEO of General Electric
How to Get Around Town: Cars aren’t easy to come by (summer residents reserve ferries well in advance to bring their Range Rovers on island), and gridlock is notorious in town. So do like the down-to-earth locals — and they do exist — and rent a set of wheels at Easy Riders Bicycle Rentals. Nantucket is covered in cycling-friendly bike paths.
(Courtesy: Easy Riders Bicycle Rentals)
Best Way to Get there: Jet Blue may fly to Nantucket, but anyone who is anyone arrives by private plane (and it’s not unheard of for people to jet in for the day just to play a round of golf). A mega yacht will also do just fine. Mere mortals queue up for the ferries in Hyannis (in summer, you can also catch one in Harwich Port, on Cape Cod).
Fashion Statement: The Nantucket Reds from Murray’s Toggery Shop — the pink pants that the men proudly sport — cut across all socio-economic levels. And oddly, there are still some women who insist on those straw lightship basket handbags topped with a faux scrimshaw design. But these days, the status symbol of choice is a pair of shoes from Vanessa Noel, who also owns an eco-chic hotel on town.
Farm-to-Table: While the farm-to-table movement is all the rage around the rest of the country, it’s only starting to pick up steam on this seafood-obsessed island. One of the trailblazers is Ventuno, which works with area farmers and fisherman and has an al-fresco bar modeled after an Italian farmhouse.
Ice Cream That’s Worth the Wait: While the name might not scream ice cream, the Juice Bar is the place. Try a scoop of the Crantucket; do we really need to tell you what’s in it?
Lobster Roll That Will Change Your Life: It doesn’t look like much from the outside, but residents will wait in line for over an hour at Something Natural, for lobster rolls and sandwiches to bring to the beach.
Breakfast Spot: Get ready to wait some more for breakfast at Black-Eyed Susans, which looks more like a diner than the cult spot that it is. The French toast with Jack Daniels butter is heavenly.
Cocktails by the Sea: Set right on the sand, Jetties has a $1 buck-a-shuck oyster bar — or for those who want to splurge, the Veuvelicious package comes with a bottle of champagne and a dozen bivalves for $85.
Who You’ll Meet in a Café: You just might spot famous summer residents (Kathie Lee Gifford) and visitors (Robert DeNiro) at the Bean, a coffee-shop institution in town.
Local Activities: A 4x4 drive on the beach to Eel Point and Smith’s Point; the Bluff Walk in Siasconset village; surfing and stand-up paddleboarding with Nantucket Surfing.
Where to Buy Local Goods: Stop by the 28-acre Moors End Farm. A family-run farm stand, this is the place to find New England corn and ripe tomatoes.
40th Pole. (Photo: Greg Hinson/Flickr)
Best-Kept Secret Beaches: Local families head to the 40th Pole; surfers love Surfside and Cisco beaches; or check out Steps beach, which only reveals itself at low tide (wade out to your own sandbar).
Island Lingo (aka how they’ll know you’re not a local): Since the accents here are from all over, there’s no need to worry, but year-round residents might label you a “washashore” or a “round the Pointer,” referring to the people arrive on the ferries past Brant Point lighthouse (see below).
Best Family Hotel: In the heart of town, the two-year-old Nantucket Hotel & Resort has one- to four-bedroom suites, many with kitchenettes. On Saturdays from 6-8 p.m., there’s a free kids’ club, so that mom and dad can have a quiet cocktail together.
The postcard-friendly Brant Point Light. (Photo: Massachusetts Office of Travel & Tourism/Flickr)
Best Resource for House Rentals: This is the land of the $100,000 weekly rental, but how about a small cottage in Old Madaket for $1,800 a week through Nantucket Real Estate?
Best Spots for Little Ones: The protected Childrens Beach; stargazing at Loines Observatory.
Favorite Lighthouse: The island has three working lighthouses, but we adore the squat Brant Point Light, which greets ferries arriving in Nantucket harbor.
The Case for Martha’s Vineyard - by Katie Weisman
(Photo: Getty Images)
Compared to Nantucket, which — let’s face it — is essentially a sandbar, Martha’s Vineyard boasts beaches, rolling farms, and forests. And unlike its uppity neighbor island, where designer duds are de rigueur, the Vineyard vibe is comfortable and laid-back. There are scores of galleries and antique shops, and if you’re hungry, dining options at all price levels, from fried clams to foie gras, in every village. Each Vineyard town has its own distinct personality and architecture, from the charming Victorian Gingerbread homes in Oak Bluffs to the Federal and Greek revival whaling captain’s homes in Edgartown.
Population: 15,000 year-round; 115,000 during the summer.
Famous Faces: Barack & Michelle Obama, who are coming back this summer; David Letterman; Larry David; Carly Simon; Adam Sandler.
Popular Way to Get Around Town: Mopeds, but don’t use them, please. Instead, rent a car, take a cab, ride a bike, or take the remarkably efficient public transportation.
Boating from Edgartown. (Photo: Lori Holder-Webb/Flickr)
Best Way to Get There: Private jet, of course. But if those are not an option, Jet Blue, Delta, and Cape Air offer seasonal flights. On weekends, young execs and co-eds opt for the Seastreak fast ferry that leaves from a handful of metro New York docks. It’s better known as the “Vomit Comet” thanks to a full cash bar and a six-hour, often rocky and upwind voyage. But hey, there’s no traffic. Seastreak offers a tamer one-hour trip from New Bedford, while the Vineyard Fast Ferry from Quonset, RI takes 90 minutes. Vacationing families, with cars packed with pets, suitcases and a few kids generally opt for the old-fashioned Steamship Authority ferry crossing from Woods Hole. Clam chowder and seagulls make this option the most authentic.
Farm-to-Table: The Vineyard is home to many farms that sustainably produce organic vegetables, meats, poultry, and dairy products, and island chefs are increasingly using local foods in their creative cooking. But no one does this more proficiently than Chris Fischer, chef of the Beach Plum Restaurant at the inn of the same name, and operator of his family’s Beetlebung Farm.
Saltwater taffy from Scoop Shack. (Photo: David Berkowitz/Flickr)
Ice Cream Worth the Wait: The impossibly small Scoop Shack in Edgartown serves up original flavors, such as green tea with local honey and mint, made daily in small batches.
Lobster Roll that Will Change Your Life: It’s astonishing how a sandwich can stir up such a debate. Some swear by those from Larsen’s, a Menemsha fish market opened by offshore fisherman Louis Larsen and his wife Mary back in 1969. Others, however, adore those served up by local churches and the American Legion Post 257 in Vineyard Haven.
Breakfast Spot: Behind the Bookstore, a tiny oasis behind Edgartown Books and hidden from that town’s bustling Main Street. Try the giant cappuccino — they’ll make a cute design in the froth!
Cocktails by the Sea: Henry’s Bar at the Harborview Hotel in Edgartown. Sip a Culebra, concocted with chili house-infused tequila and cold, crushed watermelon juice on the grand porch overlooking Edgartown Harbor at sunset.
Who You’ll Meet in a Café: Norman Foster or Meg Ryan at Espresso Love in Edgartown.
Local Activities: The all-island bike paths; kayaking or paddle boarding on the freshwater Great Pond in West Tisbury; clamming in Cape Pogue, with a permit from the Edgartown Shellfish Department.
Where to Buy Local Goods: The West Tisbury Farmer’s Market showcases goods from the Vineyard’s best and oldest farms, including Allen Sheep Farm & Wool, and the Grey Barn and Farm. Seasonal farm stands at Morning Glory in Edgartown and Bayes Norton Farm in Oak Bluffs.
Best-Kept Secret Beaches: Great Rock Bight, in Chilmark. There’s also Lucy Vincent beach, but alas, it’s private. However, if you charm a driver, you can hitch a ride and get inside the locked gate.
Island Lingo (aka how they’ll know you’re not a local): When you order a milkshake or chowder instead of a frappe and chowdah.
Where to Get a Peek at Island History: Walking around the Tabernacle and the Campgrounds in Oak Bluffs. This magical site features fairytale gingerbread cottages that now stand in the place of tents once pitched for 19th century religious camp meetings. The Martha’s Vineyard Museum provides visitors with a complete history of the Island.
Some local chowdah. (Photo: David Berkowitz/Flickr)
Most Romantic Hotel: The Charlotte Inn, a Relais & Chateaux property in Edgartown owned by Gerret and Paula Conover, is impeccable yet cozy with its English country décor and tidy gardens.
Best Family Hotel: The grand Harborview Hotel in Edgartown dates to 1891. With its turn-of-the-century roots, it has large family cottages, in addition to suites and rooms. A heated pool and a seasonal kids’ program, along with a family-friendly gourmet restaurant (Water Street), makes this a great vacation spot for all ages.
Best Resource for House Rentals: Sandpiper Rentals has listings for everything from tiny in-town cottages to grand homes with stunning ocean views.
Best spots for little ones: State Beach on Vineyard Sound — no waves! Same with the freshwater ponds on the inland side of Long Point Wildlife Refuge, with a permit from The Trustees of Reservations. What else? The landmark Flying Horses carousel and any and all candy shops.
Favorite Lighthouse: Aquinnah lighthouse on the cliffs — most beautiful at sunset.