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Martha’s Vineyard for First-Timers

Photo by Kim Grant

Two perfect days on Martha's Vineyard

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A few quality lodging places on Martha’s Vineyard accept one-night stays. But you’ll do yourself a big disservice if you can only carve out one night on-island. That said, you can pack a great deal of experiences and sights into 36 hours — as long as you are properly caffeinated.

A Perfect Down-Island Day on Martha’s Vineyard

7:00 => Order everything (errr, anything) on the menu at Art Cliff Diner (Vineyard Haven).
8:30 => Watch the morning harbor activity from quiet Owen Park (Vineyard Haven).
9.30 =>  Wander around the whimsical gingerbread houses in Oak Bluffs.
11:00 => Sit for a spell in the solid Old Whaling Church in Edgartown.
12:00 => Have a quick lunch at Seafood Shanty, overlooking Edgartown Harbor.
1:30 => Ride the ferry “On Time” to Chappy; take a Cape Pogue Natural History Tour.
6:00 => Walk out to the Edgartown Lighthouse with a camera.
7:00 => Dine outdoors at The Dunes (at the Winnetu, Edgartown) or Sweet Life Café (Oak Bluffs), with advance reservations.
10:00 => Resolve to visit the Vineyard longer next time.

A Perfect Up-Island Day on Martha’sVineyard

7:45 => Pick up fresh donuts from Humphrey’s (Vineyard Haven).
8:00 => Take the scenic drive along Lambert’s Cove Road (VH).
9:30 => Hike the crestline trail at Menemsha Hills Reservation (Chilmark).
11:30 => Drive Tea Lane and Meeting House Road between North and South roads (Chilmark).
12:00 => Hang out on the front porch of Alley’s General Store with a sandwich (West Tisbury).
1:15 => Interact with the joyful sculptures at Field Gallery (West Tisbury).
2:30 => Explore Polly Hill Arboretum (West Tisbury).
4:00 => Visit Chilmark Pottery or Martha’s Vineyard Glass Works (both in WT).
5:30 => Stroll the beach beneath the Clay Cliffs of Aquinnah.
7:30 => Watch the dusky light change color at Menemsha Harbor.
8:00 => Enjoy clam chowder or lobster rolls at Larsen’s or the Fish Market (both in Menemsha).
10:30 => Split a Mad Martha’s ice-cream cone with your partner (multiple locations).

Do yourself a favor and try to stay three or four nights. Base yourself in Edgartown, Vineyard Haven or Oak Bluffs and spend one whole day exploring up-island.

If you have time, pair a Vineyard visit with a quick day trip to Nantucket or a longer trip to Cape Cod or Boston.


Excerpted from Cape Cod, Martha’s Vineyard & Nantucket, An Explorer’s Guide. For full-on details about these ideas (and many more), pick up the guide on Amazon.


At A Glance

Price Range:
budget
midrange
luxury
Most Suited to:
single
couples
families
groups
lgbtq
Season:
winter
spring
summer
fall
Length:
weekend
longer

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