"Down island" refers to the eastern towns of Oak Bluffs, Edgartown, and Vineyard Haven. These are the busier port towns on the island.

Downtown Main Street:

Hit the shops, enjoy some ice cream as you stroll, grab lunch (and a mudslide) at the Seafood Shanty, and snap some pics at Memorial Wharf.

Bad Martha Brewery:

On upper Main St, check out the brewery and tap room. Time it right and enjoy some live music!

South Beach (Katama):

This is a public beach that is walking distance from the Winnetu. There is also parking if you are not staying at the Winnetu and still want to enjoy some surf!

OB Harbor:

Grab some lunch or a drink and sit along the harbor. Watch the boats, the sunset, or the people. (We recommend the "Mommy's Helper" at Fishbones!)

Joseph Sylvia State Beach or Inkwell Beach:

These are public beaches in OB. Inkwell Beach is walkable from downtown OB. State Beach is a short drive outside of town.

(Driving towards Edgartown, State Beach beach is wear you'll find the infamous Jaws Bridge!)

The Flying Horses:

Check out the oldest operating carousel in the country! Good luck grabbing the brass ring!

Circuit Avenue:

The street for shopping in OB.

Nomans:

Just outside of town, this is a cool spot to grab a drink and hang on the lawn or in the shade. They have jenga, cornhole, Connect 4, etc.

Golf:

Allegedly Farm Neck Golf club is open to the public? No clue if this is true but check it out.

Main Street:

This the shopping street in Vineyard Haven. If you're in the mood for a coffee, check out Mocha Motts!

Golf:

Allegedly Mink Meadows is open to the public. No clue if this is true, but good luck.

Mini golf at The Cove:

The preeminent form of golf!

Visit all of the spots that made Shay Hill into the man he is today! The list below follows his employment journey, but complete your bar crawl in whatever order your choose!

The Wharf Pub, Edgartown

Harbor View, Edgartown

Alchemy, Edgartown

Sharky's, Oak Bluffs

Dos Mas, Oak Bluffs

SandBar, Oak Bluffs

Up Island towns:

"Up island" on Martha's Vineyard refers to the more rural, western towns on the island. (Does this make sense? Absolutely not.)

Menemsha: nice little fishing village on the western coast of the island. They have a little beach, a few fish markets where you can grab a bite, and one of the best views of the sunset. In the mood for an ice cream treat? Hit up the walk-up window at the Texaco.

Aquinnah: If you have a car and are up for the trek, Aquinnah is the western-most town with beautiful views. Check out the views of the Cliffs and the Gay Head light (former name of the town).

Chilmark: As you meander your way up to Menemsha or Aquinnah, you will pass through Chilmark with pretty views of some farms. The Chilmark Flea Market happens on Thursdays and Saturdays.

West Tisbury: Poke around Alley's General Store, stroll over to the field gallery, and check out the Farmer's Market at the Ag Hall.