Moshup Beach (public)

Nestled in a serene hillside, Outermost Inn offers stunning views of Martha's Vineyard, along with exquisite cuisine, cozy rooms, and warm hospitality.

Orange Peel Bakery in Aquinnah serves up fresh, wood-fired pizzas and standout baked goods—from croissants to scones—on the honor system.

Tucked away at the Gay Head Cliffs, The Aquinnah Shop offers delicious seafood and hearty fare paired with breathtaking sunset views over the water.

Aquinnah, a quaint town on Martha's Vineyard, charms visitors with its breathtaking clay cliffs and scenic winding roads, far from the hustle of life.

Sarma serves vibrant, inventive Mediterranean small plates in a lively, colorful Somerville spot with a buzzing bar and standout dishes like Black Sea cornbread and fried chicken.

Luxury harborfront hotel with plush rooms, harbor views, spa, jazz lounge, and a maritime museum, steps from Boston's lively waterfront.

Boston's Museum of Fine Arts dazzles with a sprawling collection from ancient Egyptian treasures to Impressionist masterpieces and modern art gems.

Dbar is a chic New American spot in Dorchester that transforms into a vibrant gay nightlife hub after dark, boasting a stunning patio and a lively brunch scene.

Larsen’s is a classic Menemsha seafood spot serving fresh steamers, chowder, and lobster with a no-frills, harbor-side vibe.

Contessa, perched high on the Newbury Hotel, offers a glamorous Italian dining experience with breathtaking city views, perfect for special occasions.