As a born and bred New Englander, I’m embarrassed to admit that I’ve never ventured up to Maine. With a reputation that boasts beautiful coastlines, boundless adventures, and a buzzy food scene, Portland felt like the perfect place to book a last-minute vacation this summer. My Ralph Lauren Americana sweater will save me from chilly nights near the water, and my Staud netted handbag couldn’t be more on-brand for an afternoon spent lobstering with locals. I’ll make sure to pack my favorite Madhappy hat and my go-to Girlfriend collective sports bra that can easily double as a casual daytime top while out and about. For practical (and posh!) footwear, I’m packing my pearly Arizona sandals, which will come in handy for rocky beach walks that will roll right into dinner downtown.

Polo Ralph Lauren flag cotton crewneck sweater

Girlfriend Collective Paloma bra in haze

Madhappy Classics dad hat

Arizona Love pearl-embellished sandals

Ian Malone, Experience Manager

I’ve gone to Martha’s Vineyard every summer of my life. The Vineyard is more casual than other resort destinations—you’ll find no black tie galas, model-filled yachts, or designer pop-up shops—but that is part of its magic. The air is clearer, the energy is calmer, and the stars are brighter. John Belushi credited the island as the only place he could get a decent night’s sleep. The Kennedys, Clintons, and Obamas find refuge along its beaches. A perfect August evening consists of Shakespeare at the Tisbury Amphitheater followed by a lobster feast at L’etoile. For more casual fare, head up island to the Menemsha Galley, which offers the best lobster roll and sunset view you’ll find.

Bode Mitchell sheer shirt

La Ligne Mr. Marin sweater

Gucci plaster pleated slub-cotton trousers

Artemis Design Co. Sumak Kilim loafers

Polo Ralph Lauren twill ball cap

Assouline x Crane Lost Fish note cards

Grace Stearns, Senior Director, Communications