Our favorite restaurant on island! They don't take reservations, but if you put your name down for a table, the wait is typically ~30-45 minutes, and you can bop around to some of the nearby bars while you wait for your table. The octopus, ceviche, and shrimp fried rice are not to be missed!
Fun and casual spot overlooking the harbor! They have an incredible outdoor deck, and is great for larger parties. We have gone for both lunch and dinner.
This is an upscale yet fun restaurant. The seafood is fantastic, and the inside turns into a dancefloor after 9:30 PM. People of all ages dance here till it is closed, including us! Reservations recommended.
A lively spot for dinner that often has a band after 9:30. We love it here for a more casual night out.
Don't let the name fool you - this cute restaurant cranks out some of the tastiest dishes on island. Dining in their back garden is a treat. Reservations recommended.
This farm to table restaurant on main street is a staple! Reservations recommended.
Another great staple! We are good friends with the owner - tell them Luke and Victoria Wolf sent you :) Reservations recommended.
Vic's favorite place for a healthy and casual lunch!
Best lobster rolls in town (in our opinion)!! Grab your lobster roll and eat it right on the harbor. You might even spot Robert on his favorite harbor bench while you wait!
Cute outdoor bar and restaurant (a part of the Faraway hotel). It's giving Hamptons but better! To dine, reservations are recommended. It is also a great spot for a drink pre dinner.
Lively spot for lunch in Oak Bluffs with the best view! Lobster roll was awarded best on island (several years in a row). No reservations but it is worth the wait. Their patio is first come, first served.
If you are staying around Oak Bluffs, you're going to want to check this restaurant out! This is Carol's go to spot for her birthday. It is fun and not so serious but so delicious! Reservations recommended.
A fun par-3 golf course on Chappy! You have to take a ferry from Edgartown but it is easy to get to by car or even bike. This is the most casual golf course on island - you can literally play in under 1.5 hours.... and barefoot if you so desire!
The cutest place for a coffee or breakfast sandwich! Carmen’s favorite spot for a slow morning.