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Posted by Aela Mass, guest blogger of

Martha’s Vineyard has much to offer — so much, in fact, that you can feel a little bit overwhelmed with choice during a short trip. But don’t worry! If you plan your day right, you can see several of the best sites on the Island in one day and you can do it with ease.

Here’s the inside scoop on 6 must-do activities for the perfect summer day!
1. Start early and hop off the boat in Vineyard Haven to enjoy Vineyard Haven Harbor Cultural District, where arts and culture and a whole lot of history collide for the only state-designated cultural district on the entire Island.
Island Home Ferry

Photo: Island Home Ferry

Stroll the easily walkable 1-mile radius and check out the Vineyard Playhouse, a wooden shipbuilder, the Island’s largest bookstore, the Martha’s Vineyard Film Society, and countless art galleries and design shops.
2. From there, head into Oak Bluffs and get a load of the gingerbread cottages! These tiny homes seem as if they’re straight from a storybook with their intricate porch detail and bright colors.

Photo: Gingerbread Cottages

Take a few minutes from your day to stroll around the Tabernacle and seize a photo op, which is sure to up your Instagram fame; the cottages truly are like nothing you’ve ever seen.
3. Next, you’ll want to experience one of the best bike rides in the world. The Island’s most popular bike path takes you between Oak Bluffs and Edgartown, and travels along the Nantucket Sound and the 7-acre Sengekontacket Pond, which means that you get to pedal between two amazing waterways.

Photo: Bike Path

The 6-mile path is mostly flat and 100% gorgeous. Plus, you can ride as much or as little as you choose! Not bringing a bike over? Not a problem, you can easily rent a bike on-Island.
4. One of the most picturesque scenes on Martha’s Vineyard can be seen from the porch of the Harbor View Hotel, so be sure to get into Edgartown. Once you’re there, wow yourself by taking the short climb to the top of Edgartown Lighthouse, and enjoy the perfect view of the harbor.

Photo: Edgartown Lighthouse

After your quick climb and sightseeing, treat yourself! The Harbor View’s in-house bar and restaurant has delicious cocktails and the best lobster salad on the Island, to name just a couple choices.
5. Keep on moving and get Up-Island; it’s totally worth the trip! Enjoy the farmland and shoreline vistas on your way to one of the most beautiful beaches in the world: Aquinnah. There, the views of clay cliffs and the red-brick Gay Head Lighthouse will stun you.

Photo: Aquinnah Cliffs

While Up-Island, also be sure to stop into Alley’s General Store, which has been in business since 1858 and will re-define your idea of general stores!
6. Undoubtedly, you will want to end your day with fresh oysters and a sunset in the fishing village of Menemsha.

Photo: Menemsha Oysters

Watch local fisherman bring catches of the day straight off their boats and into Larsen’s Fish Market. Bring a bottle of wine, and get comfy on the Menemsha Beach while you unwind from the day and watch the sun set over the water. But don’t be surprised when onlookers start clapping as the sun finally sets — it’s so beautiful, you’ll wish for an encore too!
For more information about how you can spend your time on Martha’s Vineyard, and to plan your trip to the Island, visit
Aela Mass is the Director of Member Services at the Martha’s Vineyard Chamber of Commerce. She also blogs at Babble Media. For the latest on what’s happening around the Island, follow them @visitmv.