If the devil really is in the details, then vacation planning has the potential to feel downright demonic. Choosing the location is a blast, but figuring out those day-to-day technicalities can drive the most detail-oriented traveler a bit loony. Have no fear! This itinerary maps out the best of the island to get you through a weeklong Martha’s Vineyard vacation in one piece.
Day 1: Arrive in Edgartown
It may not be the hippest topic, but it’s important to decide how you’re going to get around the island before you plan what to do there. If you’re packing your own transportation, then your car needs to take a ride on the Steamship Authority. Otherwise, leave the vehicle behind, and rely on our trusty public transportation. With a 7-day Vineyard Transit bus pass, you can see the entire island for a very agreeable rate.
Drop the bags at your hotel, and start your Martha’s Vineyard vacation by checking out the area for the rest of the day. From the classic Vineyard Vines to unique local finds, Edgartown’s spread of downtown shops can keep anyone occupied for hours. For dinner with a view, catch a lobster dish at The Seafood Shanty.
Day 2: Getting to Know Martha’s Vineyard and Edgartown
Why not get a formal introduction on your first full day? Take a trip to the Martha’s Vineyard Museum to learn about our little piece of land. After you’ve had your fill of island education, go out and explore it on your own. Get your hands on a bike, pack a picnic lunch, and head to Katama Beach for the afternoon. If you want to push the pedals even further, follow one of our island bike routes and feast on a well-earned dinner at The Wharf when you return.
Day 3: Aquinnah and Chilmark
Venture up-island with a trip to Aquinnah and Chilmark. These are some must-stop spots to hit in the area:
- The Cliffs and Lighthouse. Are we on a Martha’s Vineyard vacation or in Ireland? The beautiful clay cliffs in Aquinnah are postcard-perfect.
- Chilmark Chocolates. If you visit in the summer, you can taste some of the best chocolate around at this candy maker (but be prepared to wait in line). You’ll thank yourself for being patient, trust us.
- Menemsha Hills. Enjoy more coastal views with a hike through the Menemsha Hills Reservation Trails.
Enjoy lunch at Orange Peel Bakery and dinner at Chilmark Tavern before heading back to Edgartown.
Day 4: Tisbury and Vineyard Haven
Only twenty minutes from Edgartown lies the seaside village of Vineyard Haven. Head out to sea with a sailing excursion on The Black Dog Tall Ships or control your own kayak from Eco Adventures. For indoor fun, catch a show at the local favorite Martha’s Vineyard Playhouse or enjoy a meal and knock some pins down at the Barn Bowl & Bistro.
Day 5: Oak Bluffs
Ready for another iconic island day? Follow the shoreline north to Oak Bluffs. The Martha’s Vineyard Camp Meeting Association (MVCMA) has anunassuming name, but these cottages are what your gingerbread house dreams are made of. Summer walking tours are available, and a pop into the Cottage Museum will give you a peek at the typical cottage interior. If you’re in the mood to fill some shopping bags, extend your stroll to Circuit Avenue for a smorgasbord of shops and lunch stops.
If you have a soft spot in your heart for animals, then we insist on a stop at Island Alpaca while you’re in the area. Visit the furry friends on this family-run farm and take a gander through the gift shop. An alpaca blanket may not come in handy on this visit, but it’ll sure bring back Martha’s Vineyard vacation memories each winter.
On the way back to Edgartown, stop by Bad Martha Brewing to get a taste of some good local beer. For an affordable and generously portioned dinner, head around the corner to Sharky’s Cantina.
Day 6: Visit Chappy
Spend the last day of this vacation in Chappaquiddick, our neighboring island. Hop on a quick ferry ride (bring a bike if you’d like!) and explore the small, quiet island. Take a peaceful stroll around the white sand beaches and boardwalks at Wasque Point, or go on an exciting oversand excursion to the Cape Poge Lighthouse. The little island is also home to the beautiful Mytoi Japanese Garden, perfect for a bit of vacation meditation.
Whether you spend a full day or a half-day here, make sure you leave time to stop by any shops or snack spots you missed back in Edgartown. For dinner on this final night, treat yourself to a meal at Chesca’s Restaurant (make sure you leave room for dessert).
Day 7: Leaving Edgartown
Say so long to your Martha’s Vineyard hotel and head to Espresso Love for some ferry ride fuel. Enjoying a bagel breakfast on the outdoor patio is the perfect way to reflect on the trip before officially heading out of town.
Since this Martha’s Vineyard vacation will make you an island insider, you’ll be set to plan your next trip and play the tour guide role. Will you bring a family member, friend, or travel solo?