Visiting Martha’s Vineyard: How to Spend 48 Hours (or Less) on Our Island

Think you need a full week to get acquainted with Martha’s Vineyard? Try 48 hours or less (really). Yes, spending several days beachside is as dreamy as it sounds, but you’re far from out of luck if time isn’t on your side. From finding your morning jolt to visiting iconic sights, we’ll show you how visiting Martha’s Vineyard on a 48-hour timeline is done.


Visiting Martha’s Vineyard: How to Spend 48 Hours (or Less) on Our Island

Mother's Day Martha's Vineyard


Day One

Arrive in Edgartown

After taking your ferry of choice to Vineyard Haven or Oak Bluffs, hail a cab or hop on the bus to Edgartown and spend your first day exploring the area. For such a walkable downtown, sometimes even we’re surprised at how easily the hours pass in Edgartown’s boutique and specialty stores (time flies when you’re filling shopping bags!). If a walk through history is more your speed, the Edgartown Historic District (which dates back to 1641) won’t disappoint. You’ll see some of the oldest buildings in Edgartown, including the Old Whaling Church, built in 1843 by shipwrights for the town’s sea captains. And since no island visit is complete without a lighthouse, end the day with a sunset visit to Edgartown Harbor Light before giving your feet a well-deserved dinner break — our best recommendation is just a walk across our porch, at Chesca’s. Don’t pass up their Espresso Martini or dessert menu while you’re there. 


Day Two

Wake Up and Smell the CoffeeDowntown Edgartown Shops & restaurants

Breakfast is the most important meal of the day so fuel up before you get too far out the door. Should you be staying at Vineyard Square between May and the end of October, you can find a mouthwatering breakfast spread right off our lobby. If you’re looking to explore Edgartown more, there are plenty of morning meals a short walk away. On Dock Street, tucked between a bike rental shop and The Black Dog kids clothing store, you’ll find the Dock Street Coffee Shop, open every day for breakfast and lunch and a favorite of islanders and locals alike. Another local favorite is Behind The Bookstore on Main Street, where you’ll find warm rice pudding, johnnycakes, and locally made granola to pair with your pour-over coffee.


Bike It, Beach It, Or Both

After fueling up with a hearty breakfast, get your body moving and explore the island by our favorite mode of transportation: bicycle. Here at Vineyard Square, we have a whole fleet of bikes available for guests to take for a spin, but if they all happen to be spoken for you can also rent a ride from nearby Edgartown Bicycles or Martha’s Vineyard Bike Rentals.


There are over 44 miles of bike trails on the island (including a hefty 100 kilometer full-island loop) but to get the most bang for your bike ride on a short timeframe, take the 6-mile Beach Road from Edgartown to Oak Bluffs. Along the way, stop at State Beach to take a dip in the water or watch daring swimmers dive off the iconic Jaws Bridge. Once you roll into Oak Bluffs, you’ll have plenty of options for how to spend the afternoon. Circuit Avenue is home to boutique shops, clothing stores, and tasty spots to grab an afternoon coffee or ice cream cone. We suggest setting aside time to see the historic Flying Horses Carousel, the oldest platform carousel in the country, and the picture-perfect Gingerbread Cottages the Vineyard is known for. If you’re a beer fan, this is also your chance to grab a midday bite and pint at Offshore Ale Co., Martha’s Vineyard’s premiere brewpub.


Gingerbread Houses in Oak Bluffs


From Farm (and Sea) to Your Plate

For your final night on the island, experience the culinary stylings that bring the farm and sea straight to your table. Venture over to West Tisbury and experience a dish at State Road, a farm-to-table restaurant that has earned the praise of Boston Magazine for its Grilled Spanish Octopus, Nova Scotia Halibut, and Wild Crab Gazpacho. Or, for another night of dining in Edgartown, indulge in the locally-sourced delicacies of l’étoile, a chef-owned and operated restaurant with a seasonally-inspired menu.


Feeling an after-dinner drink? Dip into Edgartown’s nightlife and let Alchemy shake up one of their signature cocktails for you — trust us, there’s a reason they’ve won Martha’s Vineyard Magazine’s Best Cocktail spot multiple years in a row.


Visiting Martha’s Vineyard in just two days is ample time to dip your toes into what our island has to offer. If you’re craving an even longer stay after your departure, though, don’t be shy — Vineyard Square will happily assist you with planning a full island itinerary.



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