9AM: The Vineyard has activities for days, and a little morning sailing sounds like the most whimsical way to start the day. And what’s sailing without some nautical stripes?

12PM: Nothing beats New England clam shack fare. High-waisted shorts (paired with a pearl necklace, of course) are the perfect casual bottoms for such a low-key experience. As a bonus, they slide on perfectly over your bathing suit.

2PM: It’s the Vineyard, so the beach is a given. A printed one-piece makes for the ideal preppy option.

4PM: When temps cool off, it’s time for some antiquing. Like any good New England town, the Vineyard has plenty. In my summery dream, I’m wearing this retro-inspired dress.

7PM: It’s been a long day, so go ahead and indulge your palette. It’s a given that stellar restaurants are everywhere in this huge tourist destination. And for the attire? This dress is dark enough for night, but breezy enough to bring in that beach mentality.

Countdown to summer… commence.

Our Head-to-Toe Preppy: From Plaid Skirts to Polos Boutique is open now.

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