The Ultimate Guide to Honeymooning in Martha's Vineyard

Martha’s Vineyard is one of those storied destinations that has all the makings of a quintessential New England getaway. There are casual and fine dining options galore, plus a plethora of charming hotels, boutique B&Bs, and nautical-inspired vacation rentals. There are beautiful beaches where you’ll want to spend all day sunbathing in between bites of New England-style lobster rolls. And there are, fittingly, historic towns with countless treasures to uncover at every turn. In short: It’s one of the best stateside honeymoon havens, where laidback luxury and romance go hand in hand.

So it’s no wonder celebs like Spike Lee, Carly Simon, and David Letterman have all called the island home and regulars like Meg Ryan, Larry David, and Reese Witherspoon can be seen each summer at the local haunts. Even the Obamas just bought a home in Edgartown!

But if you’re a first-timer to the area, looking to hit all the Vineyard high notes with your partner, allow us to point the way to our must-visit favorites—with the help of a few travel experts.

Why Is It Called Martha's Vineyard?

While there are many theories on how MV got her name, there isn’t necessarily one correct answer. According to Wall, the name is said to come from the daughter of Bartholomew Gosnold, an Englishman who led the first recorded expedition to Cape Cod in 1602.

Where Is It Located?

“Martha’s Vineyard is located in southeastern Massachusetts and lies about seven miles off the southwest corner of the Cape Cod peninsula, across Vineyard Sound from the Elizabeth Islands,” says DeSousa. This low-key, scenic "vineyard" (which actually comprises many vineyards, farms, and sweet hamlets) is relatively easy to access, especially compared to its smaller, further counterpart, Nantucket.

Why Honeymoon on Martha's Vineyard?

“Martha’s Vineyard’s natural beauty and romantic places make it an ideal destination for a romantic getaway together,” shares DeSousa. “There’s a wide selection of outstanding, candle-lit eateries, stunning spots for hiking, cycling, and touring, plus outstanding beaches for hand-in-hand strolls at ethereal Menemsha, Mytoi, Chappy, Lambert’s Cove Beach, or Lake Tashmoo, where unforgettable moments are created.”

How to Get There

Since this “vineyard” is technically an island, you do need to arrive by ferry or plane and can’t simply drive straight over. That’s all part of the adventure of getting there, though! If you plan on staying for a week or longer and want a car for ease, your best bet is to take the ferry. 

“There is year-round service to and from Martha’s Vineyard aboard the Steamship Authority ferries (for both walk-on passengers and motor vehicles) between Vineyard Haven (year-round) and Oak Bluffs (seasonal),” explains DeSousa. “There is also seasonal service to/from Martha’s Vineyard on Island Queen (from the end of May to early October) and on-demand service aboard Patriot Party Boats from Falmouth to Edgartown via their vineyard shuttle and water taxi.”

Honeymooners traveling to MV from Rhode Island, New York, or New Jersey have the option of booking the Fast Ferry from North Kingston, RI; the SeaStreak from New York/Northern NJ and New Bedford; and Hy-Line Cruises between Hyannis and Oak Bluffs, but once your journey ventures beyond these access points, DeSousa recommends flying.

“There’s a growing number of carriers providing seasonal service to and from Martha’s Vineyard from Boston’s Logan Airport, New York’s JFK Airport and private aircrafts are welcome with advance planning and parking at MV Airport (MVY),” he adds. Flights are about an hour, while the ferry takes just 45 minutes. (More information on these flights can be found on Get to MV by Plane.)

When to Visit

The summer months are ideal for a Vineyard getaway to fully enjoy the beaches and quintessential New England charm, but late spring and early fall also make for a less-busy time to visit. Hotel rates are highest from May through August when you usually need to book restaurant reservations and ferries in advance (especially if you plan on bringing a car with you).

If you’re looking for fewer crowds and less inflated prices, Wall suggests honeymooning during the month of September, which is considered one of the best months to visit the Vineyard. "The weather is warm enough to still enjoy a beach day and jump in the water, but the summer crowds are gone. The restaurants are all still open, giving you a chance to taste all of the local favorites without long wait times, she says. "Evenings can be chilly, but this adds to the romanticism of a honeymoon on an island in New England,” Wall adds.

How Many Days Should You Stay?

“Four days is the perfect amount,” says Wall. “This gives you a safety blanket in case it does rain one or more of those days since you will want at least one full beach day, and the ability to visit multiple towns on the island during your trip.”

Things to Do in Martha's Vineyard

There are six towns on the island, each with a different personality and signature vibe. “Up-Island”—a phrase that goes back to the whaling days—you’ll find West Tisbury, Chilmark, and, furthest out, Aquinnah. Head here to run into James Taylor and spend your days by the cliffs, beaches, and lighthouses.

The other three towns are Vineyard Haven, Oak Bluffs, and Edgartown. There is also a separated, “mini” island, Chappy (Chappaquiddick) off Edgartown. These three towns are more bustling than up-island, with a slew of restaurants, shops, and hotels to take advantage of. Depending on your preference, either side of the island has plenty to offer, and the drive from one end to another is just shy of an hour.

In terms of getting around, the best way is by bike—preferably with a wicker basket in tow for romantic beach picnics. Wheel Happy is a full-service bike rental, sales, and service shop with two locations on the island and they'll even deliver bikes to your hotel. Renting a jeep and driving out on Norton Point Beach is another pastime if you prefer to be on four wheels. And for those who want to get out on the water, consider booking a boat excursion. “A sunset cruise on the Black Dog Tall Ships or Mad Max Catamaran is a must,” says Wall. Similarly, DeSousa suggests booking a full moon paddle with Island Spirit Kayak or taking a see-through illuminated acrylic SUP board on Sengekontacket Pond for a once-in-a-lifetime romantic experience.

Honeymooners in search of adventure should hike Menemsha Hills—and of course, follow it up with lobster rolls from Menemsha Fish Market while enjoying the sunset. You can also explore the island's miles of sandy beaches, rocky coasts, and coastal dunes by horseback. “We recommend ESPARANZA RIDING COMPANY for their Paso Fino horses—smaller Spanish horses that have a smooth gait and are well-mannered, making them the perfect trail horse,” explains DeSousa.

Speaking of beaches, head to South Beach, a (free!) public barrier beach that offers huge waves and great sand. “It was also famously one of the filming locations for Jaws”, notes Wall.

“And by all means, end your night standing in line to get fresh-from-the-oven donuts at Back Door Donuts in Oak Bluffs,” says DeSousa. This is an island rite of passage!

Where to Eat

Not sure where to head for your first romantic oceanside meal? Jamieson advises trying out Atria in Edgartown. “Book a table outside at this upscale spot for a romantic dinner,” she says. “The gardens are stunning!” Also at the top of her list is Noman's in Oak Bluffs. “They have a huge lawn with an outdoor seating area and games—an ideal spot to bring your dog and kids.”

For those heading to the Chilmark area, DeSousa recommends Larsen’s Fish Market. "Larsen’s has all the classics cooked to order from clam chowder and lobster to stuffed scallops,” raves DeSousa. “Visit for lunch or stop by mid-afternoon to avoid the evening rush that accompanies Menemsha’s famous sunsets.” 

If you happen to be staying at the Harbor View Hotel on your trip, Bettini’s bar will most likely become your honeymoon headquarters. Known for some of the friendliest bartenders on the island, it’s a great spot to grab craft cocktails after the beach or share Champagne while you’re waiting to check into your room. The restaurant is tops for fresh coastal cuisine and they’ve added a stunning, exposed brick wine room that was made for intimate pairing dinners for two.

And of course, finding a good lobster roll is a must. Look no further than Katama General Store near Edgartown. Known for one of the best lobster rolls on the island, you'll want to call the day before to place your order at this recently-expanded market, then take lunch down to South Beach to enjoy in the sand.

The Best Hotels in Martha's Vineyard

DeSousa loves the Harbor View Hotel in Edgartown with 117 rooms and suites, plus an on-site pool and spa, and two restaurants. “It’s the island’s most celebrated and sumptuous hotel located on North Water Street, fronted by the beautiful Edgartown Lighthouse,” he says.

For a Vineyard Haven option, DeSousa is partial to Mansion House—a sprawling inn with 48 rooms that dates back to 1794, when it was once the grande dame of Main Street. “There’s a health club, spa, cupola for viewing the harbor, and rooftop yoga just around the corner from the ferry and downtown Vineyard Haven.”

The Hamptons may have Gurney’s, but Martha’s Vineyard has the New England equivalent: Winnetu Oceanfront Resort. Each of their 58 suites, studios, and private cottages is equipped with air conditioning, kitchenettes, and separate living areas, but the biggest draw is that many have unobstructed ocean views. This chic resort also has two pools (with poolside cabanas), a fitness center, a shuttle service downtown, massage and spa services, and tennis courts. You also can’t beat their prime real estate address: besides the natural dunes, steps from South Beach in Edgartown.

Over on the Oak Bluffs side, The Pequot Hotel is quirky-cute with 32 rooms with loads of complimentary perks. “There’s iced tea, lemonade, and fresh-baked cookies in the afternoon, Sunday morning mimosas, and daily breakfast,” says DeSousa. Who is also quick to point out that this honeymooners’ hideaway is well-suited for couples looking for an affordable abode, thanks to amorous amenities such as a front porch with rocking chairs, bike rentals delivered to the hotel, and an outdoor shower in the back garden.

Lastly, The Edgartown Collection is a conglomerate of four unique hotels (The Richard, The Edgartown Inn, The Christopher, and The Sydney), but the last two get our vote for the best honeymoon hotels with all the bells and whistles. For starters, they are steps from Edgartown’s galleries, specialty shops, and gourmet restaurants, and feature manicured grounds, in addition to well-appointed guest rooms within a magnificent 1892 Victorian home.