A historic whaling town with unique white houses and brick sidewalks. Walk up and down the small streets around the downtown area, checking out the local shops and sites.
Great public beach in Edgartown/Katama - surf can be a bit more rough than at State Beach.
This is the more calm beach. It's a great family beach when you're on your way to/from Edgartown and Oak Bluffs. Park anywhere along the street, and make sure you drive by the Jaws bridge to watch people jump!
Cute beer garden with corn hole and live music! Could be a fun place to meet up before the wedding. It is walking distance from all Edgartown hotels, but closest to the Edgar Hotel.
Perfect place to grab a cocktail and a few fresh oysters!
Great place to grab some fried fish for lunch with roof top views of Edgartown harbor.
Coffee shop and kitchen on main street in Edgartown. Serving breakfast, lunch and dinner. Big fan of their avocado toast #basic
Great dinner place (they do not take reservations)! It's also boat themed, and what's more Frank than that?!
Love this place for dinner in Edgartown! While it's not necessarily small plates, we'd still recommend sharing a bunch of different things.
Casual breakfast spot where you can watch the bi-planes take off and land in Katama
This is where you'll find the iconic and colorful “gingerbread houses." Walk down Main Street to check out the shops or the Tabernacle (a natural historic landmark). Take a ride on the Flying Horses carousel, the oldest working indoor carousel in the country (try to catch the lucky Brass Ring and win a free ride)! Or, grab a drink at any bar in Lobsterville!
This would be a great place for a group of people to meet up on Saturday before the wedding. It is a big OUTDOOR space. It has fun lawn games, good drinks, and sometimes live music.
Best sushi and lobster rolls on the Vineyard. Make sure to say hi to Will's sister (groomsmen) when you're there!
If you haven't had a Dirty Banana yet, this is a MUST. We try to have at least 5+ per season. He may no longer be mixing them up at his shack, but if it's open, definitely order from Donovan's Reef.
Casual bar that makes their own beer, has good food, and allows you to eat (and throw on the ground) as many peanuts as you want!
Whether late night or early morning, the apple fritters at Back Door Donuts are legendary. Spoiler alert: we'll have some at the wedding!
Vineyard Haven is another cute town! Walk down Main Street for cute shops and quick bites. The Steamship Authority ferry from Woods Hole arrives and departs from here.
Best brunch of the Island. There can be a bit of a wait sometimes, but we're thinking in late May you should be OK. Celebrities such as The Obamas, Meg Ryan, and John Cougar Mellencamp are sometimes spotted here.
Great coffee - just make sure you bring cash! There's one in Oak Bluffs too.
This is the more remote part of the island with lots of breathtaking scenery. You'll want to have a car or hop on a bus to explore. This is our favorite part of the island to take visitors on an 'Island Tour'.
This is a great hike (or for hikers, more of a nature walk) with beautiful vistas, ending up at the Ocean. The hike doesn't take too long - maybe 1-2 hours?
Menemsha Beach is the top spot on the island to watch the sunset. Feel free to BYOB for a picnic on the beach. Make sure you take a photo!
Located in Menemsha harbor, the fish could not get any fresher! This may just be a fisherman's shack, but a hot or cold lobster roll on the beach during the sunset cannot be beat. Arrive early as there is usually a crowd.