Let’s talk Sarah Flint. I have yet to meet her, but I just love her. I love that at the age of 24 she started her eponymous shoe collection that carries a range of heels, flats, and sandals as covetable as one can imagine (ahem, as seen in almost every Instagram picture I have taken of late). I equally fawn over her seemingly immediate (and widespread) success at such a young age, with her collection moonlighting in Bergdorf’s, Barneys, and Shopbop.

And while I am personally a Flint footwear fanatic, I happen to be in mighty good company with Kate Hudson, Blake Lively, and Jessica Alba, who also adore Sarah’s designs. The lady has incredible taste, which is perhaps an extension of her New England savoir-faire, that combines both a classic aesthetic and a modern twist. Polished and sexy. Timeless and ever so chic. This is why I couldn’t think of a better person to guide us through Martha’s Vineyard – where class and charm mix like a perfect Pimm’s cup, and sailing trips are de rigeur. Take it away, Miss Sarah! You’ve got a fan in me for life.

From Sarah

Spending my summers on Buzzards Bay directly across from Martha’s Vineyard and visiting the island has always been a summer treat! Now I go more often, but I used to sail there and spend the night on our boat once a summer with my father, uncle and cousin as a special father daughter trip. Between the beaches, lighthouses, farms and sunsets it really is such a fantastic part of New England with it’s own special feel.

Eat

State Road – State Road in West Tisbury is one of the best farm-to-table restaurants I have ever been to. Not only do they grow their own produce, but they are committed to supporting the other local farms and fisherman. The wine list is small, but excellently curated!

Art Cliff – The Art Cliff Diner is by far my favorite breakfast spot. Located in Vineyard Haven, it feels like your classic country diner. Don’t miss out on the almond crusted challah French toast! Rightfully so, there can be quite the line for a table on the weekends.

Larson’s Fish Market – Whenever we take the boat over from Buzzards Bay for a day trip we always stop at Larson’s Fish Market for lobster rolls. It is an adorable family-run seafood store and restaurant in the fishing village of Menemsha. Whether you get stuffed clams and sit at the tables outside or grab something to cook at home, the food is always so fresh and delicious.

Stay

Beach Plum Inn – The Beach Plum Inn is the most adorable little 19th century Inn perched on a hill overlooking Menemsha and surrounded by beautiful gardens and pastures. You can either stay in the main house or little cottages, both of which are lovely. The main house was actually built with salvaged wood from ship wrecks. It is also under a ten minute walk to the Menemsha Village and a public beach.

Shop

North Tabor Farms – It is hard to pick just one because there are so many amazing farm stands on the Vineyard, but North Tabor is where I like to stop. They sell everything from fresh eggs and greens to gorgeous flowers.

Midnight Farm – Midnight Farm is an eclectic boutique owned by Carly Simon; I always like to stop by. It is a very cool one-story space selling everything from home goods, shoes, bedding, toys, food, books, clothing, furniture, jewelry, and even Carly Simon CDs. They carry more known brands, but some of my favorite things they sell are the more artisanal items sourced from local craftsmen.

Chilmark Flea Market – Chilmark Flea Market is open 9am to 2pm Wednesdays and Saturdays and is located in a lovely meadow filled with homemade wares, collectibles, antiques, clothing, food, and vintage goods at a range of price points. Two years ago I bought beautiful antique blue vases of varying sizes that I use for wildflowers all summer long.

Murdicks Fudge – Incredible homemade fudge with locations in Edgartown, Oak Bluffs and Vineyard Haven so you cant miss it! You walk in and are immediately overwhelmed by the smell and can watch them make the fudge on the marble slabs right in front of you. On our sailing trips our dad’s used to always take us to buy some and bring it back to our siblings. I’m afraid most of the time we made it home with empty fudge boxes and chocolate covered life jackets.

Frolic

Flying Horses Carousel – The Flying Horses merry-go-round is the oldest operating carousel in the Unites States. I used to love to go with my cousin and try and grab one of the brass rings for which you would receive another ride free if you were able to catch one!

Aquinnah Beach – There are many amazing beaches on Martha’s Vineyard, but Aquinna is my favorite for swimming. It has the softest sand and the most translucent waters I have ever encountered. Over the years it has also become known for its unofficial “clothing optional” area.

Gingerbread Cottages in Oak Bluffs – Visiting the gingerbread houses at oak bluffs is an absolute must. It feels as though you are stepping into a picture book or village of dollhouses as you walk by the most ornate Easter egg colored cottages. Between the incredible colors and intricately carved wooden trims, as a designer it is hard not to feel inspired.

Images via: MVTimes, Hungry Native, Travel and Leisure, Condé Nast Traveler, Facebook, Pinterest, Glitter and Gardens, Carpool Candy, UpperCapeandVineyard.com