Martha's Vineyard, Massachusetts

Housed inside The Charlotte Inn, The Covington delivers an intimate farm-to-table experience where the menu shifts with whatever is freshest from local farms and surrounding waters. The candlelit dining room is impossibly romantic, with garden views that make every course feel like a special occasion. Signature dishes like seared Menemsha scallops draw devoted regulars who plan visits around a reservation here.

There is no ceremony at Larsen's, just gloriously fresh lobster, oysters, and littlenecks sold straight from a no-frills shack on Menemsha Creek — and that is exactly the point. Grab a picnic table, crack some claws, and watch the lobster boats drift in with the afternoon tide for an utterly authentic Vineyard ritual. Come early, because the best items sell out fast and the sunset crowd is notoriously loyal.

Set in a beautifully converted West Tisbury farmhouse, State Road is the island's most celebrated celebration of hyper-local ingredients, with vegetables grown steps from the kitchen. The open hearth and exposed beams create a warmth that perfectly matches food full of honest, deeply satisfying flavors. Their wood-grilled dishes and rotating charcuterie board make choosing just one entrée a genuinely delightful challenge.

Martha's Vineyard's beloved original brewpub pours handcrafted ales alongside a menu of hearty pub classics that hit the spot after a long beach day. The oak-paneled interior and live music most evenings create a convivial atmosphere where locals and visitors happily share long communal tables. Their chowder and fish tacos paired with a cold Amber Ale have become something of a rite of passage for returning summer visitors.

A jewel of Edgartown, this Relais & Châteaux property feels like stepping into a living museum of antiques and garden romance. Each room is uniquely appointed with period furnishings, oil paintings, and sumptuous linens that make every morning feel unhurried. The manicured English gardens alone are worth the splurge for a truly timeless island escape.

Perched above Edgartown Harbor, this grand Victorian landmark offers sweeping water views that glow gold at sunset from its iconic wraparound porch. Rooms blend classic New England elegance with modern comforts, and the heated pool is a welcome retreat after a day of exploring. The staff are genuinely warm and will happily arrange sailing charters right from the hotel dock.

Tucked along South Beach in Katama, Winnetu is a family-friendly haven that never sacrifices sophistication for casualness. Spacious suites and cottages come with full kitchens and private porches overlooking rolling dunes, making longer stays feel effortlessly residential. The on-site Dunes restaurant and daily beach shuttle seal the deal for a relaxed, all-encompassing island experience.

Nestled in the heart of Vineyard Haven, this intimate nine-room inn wraps guests in thoughtful luxury with locally sourced breakfasts and hand-selected New England furnishings. The innkeepers bring a personal touch that chain hotels simply cannot replicate, remembering your coffee order and offering genuinely local recommendations. Its walkable location near the ferry makes arrivals and departures completely stress-free.

These dramatic multicolored clay cliffs plunging into the Atlantic at the island's western tip are among the most breathtaking natural landmarks in all of New England. The swirling bands of red, orange, and white clay carry millions of years of geological history and hold deep cultural significance for the Wampanoag Tribe of Gay Head. Arrive at golden hour and linger to watch the lighthouse beam cut across a sky that turns every shade of flame.

The iconic red-roofed Edgartown Lighthouse stands at the tip of a sandy spit framed by bobbing sailboats and classic white clapboard architecture that defines Vineyard charm. The easy harbor walk leading to it is lined with hydrangeas in summer and offers some of the most photogenic views on the entire island. Climb the lighthouse for a panoramic sweep of Chappaquiddick Island and the sparkling sound beyond.

Run by Mass Audubon, this peaceful 200-acre sanctuary along Sengekontacket Pond offers miles of trails through meadows, forests, and marsh that feel worlds away from the summer crowds. Ospreys, great blue herons, and painted turtles are regular sightings for even casual nature walkers who take their time on the boardwalk paths. The sanctuary runs wonderful family programs and guided birding walks that deepen the experience beautifully.

Strolling through this extraordinary community of gingerbread cottages painted in candy-bright pastels is like wandering through a Victorian fairy tale that never ended. Hundreds of ornately trimmed carpenter Gothic homes cluster around the open-air Tabernacle, a cast-iron and timber landmark that still hosts community events each summer. Visit on Illumination Night in August when paper lanterns glow from every porch in a magical century-old tradition.