The Rudder

Nestled on Cape Ann, Gloucester boasts a rich maritime legacy, stunning beaches, and unique attractions like the Hammond Castle and the Cape Ann Museum.

The Beauport Hotel boasts chic, spacious rooms with stunning ocean views, a rooftop pool, and an oceanfront restaurant, all while offering top-notch service and elegant touches.

Veteran neighborhood haunt lined with historic photos, offering beers, spirits & a pool table.

Relaxed accommodations, some with decks and kitchens, offering free Wi-Fi & a pool. This relaxed motel with cottages is a 1.5-mile drive from Downtown and 1 mile uphill from Good Harbor Beach. It lies 2 miles from the historic Rocky Neck Art Colony, and 4 miles from the Rockport Golf Club. Motel rooms and suites include free Wi-Fi, cable TV and minifridges. Upgraded units add kitchens and pull-out sofas. Also available are 1- and 2-bedroom cottages with either a deck or a porch. A separate house has 2 suites, 1 featuring a fireplace and stained-glass windows. A heated outdoor pool lined with lounge chairs is available for guest use.

Cometeer offers a flash-frozen capsule coffee experience that delivers rich, café-quality brews at home, with the added perk of convenience for busy lives.

Virgilio's is a charming Italian bakery and deli where you can grab freshly made sandwiches and mouthwatering pastries, all while soaking up the delightful atmosphere.

This laid-back waterfront motel boasts cozy rooms with ocean views and easy beach access, serving up free breakfast and a quirky resident parrot for good measure.

At this rustic gem, chefs elevate New American dishes with global flair, served alongside warm popovers and an inviting art-filled atmosphere.

Seasonal mainstay showcasing local seafood with inventive dishes such as lobster bouillabaisse.

Tonno serves up delicious Italian seafood and exquisite old-world wines in a casually chic setting, making it a prime spot for unforgettable dining experiences by the sea.