Day Itinerary
8 Activities
Day 2
121 mi
Exploring Martha’s Vineyard
You’ll circle Martha’s Vineyard by car, visiting the island of Chappaquiddick, the fishing village of Menemsha, and the iconic cliffs of Gay Head before returning to Boston.
8.6 mi
1 hr 20 min
09:005 min
Woods Hole Terminal
In the morning, you’ll board the Chappy Ferry to the island of Chappaquiddick.
18.4 mi
1 hr 20 min
10:3030 min
Mytoi
Visit the breathtaking Mytoi gardens. This secluded, Japanese-style space features plantings from Martha’s Vineyard and abroad for a gamut of unique blooms. Walk the half-mile Salt Marsh path or simply sit in the shade of the pine grove for a moment of tranquility.
12 mi
50 min
12:0030 min
7a Foods
Visit 7a Foods on your way “up-island.” This West Tisbury institution has pivoted to a takeout window during the COVID-19 pandemic, but whatever old magic graces the 7a kitchen has remained. The chefs mainly deal in sandwiches, but in inventive combinations that are sure to surprise your taste buds. Asparagus and blueberry? Beet and peanut? Potato chips atop your turkey-pastrami? Trust in the magic, you won’t be disappointed.
0.2 mi
5 min
12:451 hr
Vineyard Artisan Festivals
Martha’s Vineyard tends to beget and attract artsy types. Meet them all at the Vineyard Artisans Festival: a gathering of arts and crafts creators who peddle their goods at the historic Grange Hall in West Tisbury. The Artisans Festival typically takes place Sundays and Thursdays throughout the summer, as well as select holiday weekends.
6.8 mi
15 min
14:0045 min
Menemsha Beach
The quaint fishing village of Menemsha is tucked into a bight on Martha’s Vineyard’s north shore. In this incredibly photogenic location, you’ll find a kid-friendly beach, a collection of snack shacks and antiques stores, and a working fishing pier where you can pretty much buy fish straight off the boat. Take a walk out the jetty, or search for artist Jay Lagemann’s “Swordfish Harpooner” sculpture nestled amongst the dune grass.
8 mi
20 min
15:1530 min
Aquinnah Cliffs Overlook
The Aquinnah Cliffs are perhaps the most famous sight on Martha’s Vineyard, and for good reason. The brick-faced Gay Head light sits atop a dramatic clay cliff, with brightly colored striations running parallel to the sea. You’ll definitely want to snap a photo from the top of the lookout, but don’t miss the shops lining the walkway. These shacks have been owned by Aquinnah families for generations, and are always brimming with unique gifts and tasty snacks.
22.1 mi
40 min
16:1530 min
Oak Bluffs Ferry Station
Board the ferry in Vineyard Haven or Oak Bluffs (be sure to check your reservation!) It's a 45 minute crossing back to Woods Hole. In nice weather, grab a drink from the snack bar and enjoy the views from the upper deck.
Pro tip: pay close attention to the announcements — the ferry can feel like a maze if you try to disembark through the wrong door.
Pro tip: pay close attention to the announcements — the ferry can feel like a maze if you try to disembark through the wrong door.
45.4 mi
1 hr 40 min
19:001 hr
Dillon's Local
Once you disembark the ferry in Woods Hole, it's still a long drive back to Boston. Stop for dinner at Dillons Local, a staple of the Plymouth culinary scene. A menu of traditional New England pub food pleases most palates, but they aren’t afraid to keeps things fresh with a few New American twists. Take, for instance, the Cape Cod Reuben: which replaces the corned beef typically found on this classic deli sandwich with fried local cod.
They don’t take reservations, but you can call ahead to join the waitlist.
They don’t take reservations, but you can call ahead to join the waitlist.