Take in the beautiful view from the Aquinnah lighthouse and then pop over to the restaurant for a bite to eat. Be sure to get a slice of pie!
Grab some of the freshest oysters around and a lobster roll
Open on Wednesday's and Saturdays. Shop the stands for local honey, island alpaca knits and so much more! Snack on some of the famous Egg Roll Lady treats while you browse.
Good for dinner, better for dancing! It's no wonder Jacques & Ana had their first kiss here!
Just a short walk from the Beach Plum Inn, this beach has some of the best sunsets on the island. Don't forget to clap for the good ones!
Any first timers to the island should check this out! The Flying Horses is the oldest operating carousel in America and it's been beautifully preserved. Be sure to grab a slice from Gio's across the street when you're done!
Grab a slice to go while you walk around OB and be sure to say hello to Michael!
Hiking trails
One of our favorite beaches! Guest passes included if you're staying at the Beach Plum Inn or Menemsha Inn
Just down the street from BPI the general store is a great stop to stock up on all your beach picnic provisions
One of our favorite restaurants on the island - they take special care to use as many local ingredients as possible so the menu is always changing. Be sure to book early!
Work through your flow in a beautifully restored New England Dairy barn
Frequented by the likes of Barack Obama, Steph Curry, Bill Murray and high school Jacques