A Summer Weekend in Martha's Vineyard

Whether you arrive via ferry or plane, you can jump right onto the free Vineyard Transit to get right to Edgartown. Once you get to a stop in Edgartown, all hotels are within a five-minute walking radius.

Once you have checked in (let's assume it's mid-afternoon), take a stroll through town and stop into Espresso Love for a coffee or a meal, or into Murdick's or The Candy Bazaar for a treat. Explore Main Street, Winter Street, and North Water Street, wandering into many boutiques and island shops. Be sure to stop into Nell / Nell Home, Rags (my personal favorite), the bookstore, and Portobello Road.

Walk down to the docks and admire the view, and then wander toward the Harbor View Hotel to walk down to the famous Edgartown lighthouse. Walk along Fuller Street Beach or go for a dip, or, if it's late enough, watch the sunset!

After you freshen up, make your way over to The Covington for dinner, and then to either Mad Martha's, Scoop Shack, or The Candy Bazaar for ice cream, and then call it a night; you will have lots to do tomorrow!

Wake up, you're going fishing. I know. Yuck. But this experience is unforgettable. Wear clothes you can get dirty and board the quick bus or take a bike ride to Oak Bluffs. Grab a quick coffee at the Black Dog and then make your way to the Party Boat Skipper (pre-book before) by the docks. The guys will tell you everything you need to know. Spend the morning basking in the sun or trying to catch the most / biggest fish you can. If you're staying somewhere with a kitchen, bring them home for later, or just throw them back into the water.

You'll finish around lunchtime, and it'll be the perfect time to explore Oak Bluffs. Take a walk around town and then through the historic gingerbread houses. Take a quick ride on the oldest merry-go-round in the US, The Flying Horses. Grab a lobster roll at Nancy's and then bus/bike back to Edgartown.

After you change out of your fishing clothes, it's time for a late afternoon dip. Grab a bike or take the bus to South Beach, and prepare for some big waves! The later you arrive / stay, the more the crowds thin out. Right versus left fork doesn't really matter, but I tend to go for the right fork so you can get ice cream at Katama Kitchen or a treat at Katama General Store on the way back.

Come back to the hotel once the sun starts to set, and head out for a late dinner at Bettini, the restaurant in the Harbor View. After dinner, make your way to The Port Hunter for drinks, live music, and dancing, and then call it a night whenever your heart desires!

Sleep in, and then wake up for a walk, jog, or bird-watching through Sherriff's Meadow, followed by a coffee / breakfast at either Rosewater or Behind the Bookstore.

If you're headed out on a ferry, head over to one of those towns (Vineyard Haven or Oak Bluffs) for a quick stroll beforehand. If you're taking a plane, take the bus to Morning Glory Farm on the way to bring home one of their famous pies or zucchini breads, and then continue on the bus to your flight.