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Michaela & Devin

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    Things To Do

Things To Do

1606 Restaurant & Oyster Bar

55 Commercial Street, Gloucester, MA 01930

The restaurant and bar at the Beauport is a must-see for guests. Enjoy cocktails by firepits or at the bar with breathtaking harbor views.

Tonno Gloucester

2 Main Street, Gloucester, MA 01930

Delight in expertly prepared Italian seafood in a cozy, upscale setting in the heart of downtown Gloucester.

Oak to Ember

9 Rogers Street, Gloucester, MA 01930

Experience a wood-fired culinary adventure focusing on steaks, chops, and rustic American fare with a harbor view.

Caffe Sicilia

40 Main Street, Gloucester, MA 01930

A great Italian coffee shop with excellent iced coffee and Italian sweets!

Bishco

51 Main Street, Gloucester, MA 01930

Perfect spot for lunch on the go, sandwiches, or salads.

Castaways Vintage Cafe

65 Main Street, Gloucester, MA 01930

Surfshop vibez, perfect for coffee, breakfast sandwiches, or acai bowls!

Birdseye Roofdeck Pool & Bar

55 Commercial Street, Gloucester, MA 01930

Rooftop pool & bar! Say no more. (only available to hotel guests)

Drift

3 Main Street, Gloucester, MA 01930

Casual open-air cocktail bar & restaurant.

Minglewood Harborside

25 Rogers Street, Gloucester, MA 01930

This lively bar offers casual American classics with live music and waterfront views. This is also where the wedding after party will be!

The Cut - Stage • Studio • Restaurant • Bar

177 Main Street, Gloucester, MA 01930

LIVE MUSIC every night

Pavilion Beach

Gloucester, MA 01930

Harbor beach directly in front of the Beauport. Perfect for a quick, relaxing getaway with scenic harbor views. This is also the location of the day-after beach DARTY.

Good Harbor Beach

Gloucester, MA 01930

This world-famous beach is a stunning stretch of white sand with sweeping ocean views, perfect for swimming, sunbathing, and long walks at low tide when the sandbar emerges.

Wingaersheek Beach

Gloucester, MA 01930

With its soft, powdery sand and crystal-clear waters, this beach is known for its unique tidal pools and rocky outcrops, making it a delightful spot for exploration and relaxation.

For all the days along the way
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