There’s something so luxurious about a summer weekend on Martha’s Vineyard. The exclusive feel and understated glamour of this charming island community lure visitors with its salty breeze, whitewashed cottages, and postcard-perfect harbors. Located just off the coast of Massachusetts, Martha’s Vineyard has long been a beloved hideaway for tastemakers and creatives seeking both serenity and style. Whether you're after a quiet reset or a fashionable escape, the island delivers laid-back luxury at every turn. Here’s how to spend a perfectly styled 48 hours on the Vineyard—from standout shops to local flavor and where to check in.

Where to Stay: Faraway Hotel

Set in the heart of Edgartown, Faraway is more than just a hotel—it’s an experience in modern coastal chic. With its breezy, bohemian aesthetic, nautical touches, and artful décor, it strikes the perfect balance between old Vineyard charm and cosmopolitan style. Picture handwoven accents, plush bedding, and a courtyard ideal for sipping rosé or catching up with friends beneath twinkle lights.

Where to Get Coffee: Behind the Bookstore

Tucked just off Main Street in Edgartown, Behind The Bookstore is a cozy local favorite with an upscale twist. Known for its top-tier coffee, freshly baked pastries, and peaceful garden seating, it’s the perfect place to kick off your Vineyard morning. Order the lavender latte and a breakfast bowl made with locally sourced ingredients, then find a seat under the cafe lights. It’s a vibe that gives off island-chic and calming sensations.

Where to Dine: Dinner at Atria and The Covington

A true Vineyard institution, Atria in Edgartown offers an elevated dining experience in a classic coastal setting. With a menu focused on local seafood and seasonal produce, plus an impressive wine list, it’s ideal for date nights, group dinners, or simply celebrating island time. Don’t leave without trying the truffle fries, thank me later.

The Covington brings a modern flair to the Martha’s Vineyard dining scene. Located steps from the harbor in Edgartown, the restaurant’s warm ambiance and beautifully plated dishes are a visual and culinary treat. The menu rotates with the seasons, always showcasing bold flavor and inventive technique. With its fashion-forward dining, every detail is intentional, and every dish is as memorable as it is beautiful.

Where to Shop: Style for Him & Her

For Him: Dune Men looking to upgrade their Vineyard wardrobe head to Dune, a destination boutique located right in downtown Edgartown. Here, it’s all about clean lines, modern coastal colors, and pieces that move seamlessly from beachside cocktails to boat days. Expect light linens, soft knits, and tailored shorts that embrace that island-casual-meets-elevated-aesthetic. You’ll walk out with staples that work just as well back in the city.

For Her: Slate Fashion-forward visitors won’t want to skip a stop at Slate, one of the island’s most beloved women's boutiques. Offering a curated selection of breezy dresses, matching sets, and effortless accessories, Slate perfectly captures Martha’s Vineyard's blend of elegance and ease. Think neutral palettes, textural pieces, and statement gold jewelry - ready for everything from a picnic at South Beach to dinner on the dock.