Sydney & Jeffrey
Things To Do
Cape Ann Whale Watch
Sail aboard the Hurricane II, the largest, fastest whale watching vessel in Gloucester. *mention the Gloucester Elks when booking a reservation!
Good Harbor Beach
Wide flat beach excellent for walking, body surfing, volleyball. Lifeguards, food, changing rooms, restrooms, fee for parking.
Cape Ann Harbor Tours
Cape Ann Harbor Tours is Cape Ann’s longest running boat tour company and offers the only tour that completely circles Cape Ann.
Mile Marker One Restaurant & Bar
Eat, Drink, Dance, Swim, Chill! Serving breakfast, lunch, dinner, cocktails and on our decks or in our dining room, year-round.
Seaport Grille
Seaport Grille takes pride in using the freshest ingredients and its passion to deliver superior food in a welcoming atmosphere.
Hammond Castle Museum
If you are a fan of history and architecture, you have to make a point to stop at Gloucester’s Hammond Castle. Constructed by the eccentric inventor John Hays Hammond in the 1920’s, Hammond Castle serves as a beautiful showcase for Hammond’s impressive collection of Roman, Medieval, and Renaissance artifacts.
Tonno Gloucester
Italian cuisine relies on quality ingredients sourced from local vendors for the freshest taste. As such, Tonno relies on only the freshest ingredients sourced in the Boston area. Featuring special catches right from the harbor, you can trust in Tonno to deliver an authentic Italian meal in one of the oldest U.S. settlements.
Eastern Point Lighthouse
You can drive out to the light, park and take the half mile walk out on the dog bar breakwater to the Dog Bar Lighthouse. It’s a beautiful area and a great spot for a sunset or sunrise.
Wingaersheek Beach
Known for its long sand bar at low tide, Wingaersheek is a great spot to spend a Summer day in Gloucester.
Dogtown Commons
Dogtown Common provides hikers with an incredible 3,600 acres of mysterious woods, large boulders and carved stone to explore.
Causeway Restaurant
If you want a classic seafood platter with fried clams, haddock, shrimp and fries, then you should visit The Causeway. It’s a no-frills Gloucester institution that cranks out some really good eats.