Check In

Lose your sea legs and step through our iconic double doors. Our whimsical front desk (and the helping hands behind it) will find your reservation and show you to your room. You may want to take some time to look around-our ground-floor salon and room amenities invite staring.

Day One 2 PM

Hotel Ginger

Day One 3 PM

Gingerbread Quarter STROLL THE QUARTER

Guests visiting Oak Bluffs for the first time should spend an afternoon exploring the Gingerbread Quarter. From the sweeping vista of Ocean Park to the old Methodist Campground, you'll quickly discover the offbeat charm and Easter egg color scheme. We're not Nantucket-and that's the point.

FOR STARTERS

The islandss best sushi chefs, oyster shuckers and bartenders duel for your taste buds at this packed-to-the-rafters locals haunt. Grab stools on the oceanfront rail and watch the ferries steam by

Day One 6 30 PM

The Overlook

Day One 8 PM

The Sweet Life WATCH THE SUNSET

Old and new collide at The Sweet Life, a contemporary island restaurant housed within a charming, beautifully restored Victorian home. Two years ago, owners Hal and Erin Ryerson purchased the restaurant and have since made their (fabulously fresh) mark on the town's food scene. Their deep Vineyard roots and impeccable taste inspire The Sweet Lifess six-course tasting menu-a must-try for couples.

FUEL UP

For peak energy on a sunny summer day, do as the locals do: Mainline iced coffee. Beetlebung and Mocha Motts are popular OB coffee places to start your morning. From cold brew to selections from the espresso bar, get your fix-and even stop by Back Door Donuts for something sweet. You'll find it all in town, twenty steps away.

Day Two 9 AM

Beetlebung Mocha Motts Back Door Donuts

Day Two 10 AM

Bend-in-the-Road Beach

Wind in your hair and heart pumping, do the two-mile bike ride along Martha's Vineyard's sandy coast. Whiz by dunes, tiny harbors and grey-shingle cottages before arriving at turquoise waters Bend-in-the-Road Beach. Need to show off for your date? Jump off famed-Jaws Bridge with the teens.

Go Cruising

Look outside-it's 80 degrees and not a cloud in the sky. It's the perfect afternoon for sailing. Book Catboat Charters cat boat and inspire your Insta followers with a shot in front the American Flag sail.

Day Two 2 30 PM

Boat

Day Two 6 30 PM

Ritz Café DIVE DEEP

Your high-low evening starts with the lowest of the low-OB's favorite dive bar, the Ritz Café. The Ritz is all about live music. Check out local band Auntie Em + The Bedspins or Rosie's Revue. 4 Circuit Avenue, Oak Bluff

Beach Road

Next, go upscale. Situated between Lagoon Pond and Vineyard Sound, Beach Road is a favorite of Martha's Vineyard's connected sets-from Hollywood icons to Barack and Michelle. Make yourself at home in the modern, sunny dining space and order several seafood courses.

Day Two 7 30 PM

DINE ELEVATED

Day Two 10 PM

Cardboard Box HIT THE TOWN

The Cardboard Box urges Oak Bluffs visitors to "have a drink on our porch and join the revel!" The good times roll here, with live music, DJs and plenty of dancing. Mix and mingle with Martha's Vineyard's millennial set.

The Black Dog (Dockside Cafe) MORNING STROLL

Wander down to the famed Black Dog's Dockside Cafe on Circuit Avenue and grab pastries and coffee. The morning light over Ocean Park is irresistible; Watch the first ferries of the day land and spend your last hours soaking up Oak Bluffs charm.

Day Three 9 AM

Hotel Ginger

Day Three 10 AM

Linda Jean's A BRUNCH CLASSIC

Throw on your favorite sweatshirt. Nothing beats a diner-style brunch at Linda Jeans, where eggs are made-to-order and hashes abound. Sip bottomless coffee (and maybe nurse a hangover) and fuel up on Linda Jean's hearty, familiar favorites.

Hotel Ginger A Brunch Classic

Throw on your favorite sweatshirt. Nothing beats a diner-style brunch at Linda Jeans, where eggs are made-to-order and hashes abound. Sip bottomless coffee (and maybe nurse a hangover) and fuel up on Linda Jean's hearty, familiar favorites.

Day Three 11 AM

Hotel Ginger

Day Three 1 PM

Ferry Say Goodbye for Now

Famous parting words at the Steamship Terminal? "We'll be back." 48 hours on Martha's Vineyard fly by...all the more reason to do it again. As you snap your final Instagram stories and look toward the mainland, take heart and plot your next Oak Bluffs getaway. We'll be waiting.