Best Spots of Boston and the North Shore

Singing Beach

119 Beach Street, Manchester-by-the-Sea, MA 01944

Where Noah proposed! Make a day out of it: browse for your beach read at Manchester by the Book, stop for food at Laughing Gull Cafe, and don't forget ice cream at Captain Dusty's! See the link for beach parking info and walk-on rates (or go free after 5PM).

Food: La Victoria Taqueria

6 Wallis Street, Beverly, MA 01915

This tasty little taqueria is our FAVORITE local bite. Get your food to-go and bring it to nearby Dane Street Beach for a scenic picnic. Within walking distance of the Commuter Rail.

Food: Anmol Restaurant

258 Rantoul Street, Beverly, MA 01905

The finest Indian food around.

Seafood: Woodman's of Essex

119 Main Street, Essex, MA 01929

Chowdah, fresh lobstah, and fried clams by the waterfront . . . the full New England coast experience!

Cape Ann: Manchester By the Book

27 Union Street, Manchester-by-the-Sea, MA 01944

This charming used bookstore was Anne's first workplace after college. Fiction, first editions, classics, sci-fi, history, kids, cookbooks, mystery, architecture, gardening, philosophy, nature . . .

Cape Ann: Bearskin Neck

Bearskin Neck, Rockport, MA 01966

A jetty of artist studios, shops, and Rockport's iconic Motif #1.

Cape Ann: Halibut Point State Park

Gott Avenue, Rockport, MA 01966

Beautiful walking paths and rocky coastal views.

Cape Ann: Hammond Castle Museum

80 Hesperus Avenue, Gloucester, MA 01930

Like Isabella Stewart Gardner, John Hammond was an eccentric art collector. He built a medieval-style castle on the ocean to fascinate guests and showcase his art. The architectural style varies wildly between rooms; you may feel like you're walking through a rich person's fun-house! Be sure to snap a pic in the courtyard and test out the acoustic magic in the library's whisper ceiling.

Cape Ann: Crane Estate (Castle Hill)

290 Argilla Road, Ipswich, MA 01938

This striking old mansion and lawn appear in a scene from the 2019 Little Women movie.

Beaches: Crane Beach

Ipswich, MA

Huge sand dunes with stunning views of sea and sky.

Beaches: Wingaersheek Beach

Gloucester, MA 01930

Enjoy soft sand and explore tide pools. Anne took some late-night trips here during college and saw faint bioluminescence in the water!

Beaches: Good Harbor Beach

99 Thatcher Road, Gloucester, MA 01930

Great waves for boogey boarding, and you can walk to Salt Island at low tide.

Boston: Isabella Stewart Gardner Museum

25 Evans Way, Boston, MA 02115

The most interesting art museum you'll visit. Isabella Stewart Gardner built her home in the style of a Venetian palace and filled it with one of America's finest private art collections. Anne loves the courtyard garden and Spanish cloister, while Noah wants to get a tattoo of the Saint Michael Archangel painting in the Tapestry Room.

Boston: Boston Public Library - Central Library

700 Boylston Street, Boston, MA 02116

One of the coolest places we've seen in Boston! You could spend hours looking at all the art inside.

Boston: Mike's Pastry

300 Hanover Street, Boston, MA 02113

A Boston classic. We visited on our first day as an official couple, and it's a necessary stop for all friends who visit. NOTE: They only accept cash.

Boston: New England Aquarium

1 Central Wharf, Boston, MA 02110

Buy tickets for the full experience, or stop by on your walk around Boston to see the live seal exhibit outside the entrance.

Boston: USS Constitution

Boston, MA 02129

Climb aboard "Old Ironsides," the oldest commissioned ship in the US Navy (yes, it is STILL floating and functional). Admission is free with a suggested donation to the USS Constitution Museum. An awesome adventure for kids and history lovers.

Commuter Rail (Newburyport/Rockport Line)

A great way to get between Boston and other local towns, weekend passes on the Commuter Rail are $10! Download the MBTA mTicket app for train tickets and stop at . . . 

Boston: The end of the line is Boston's North End, a hub of great Italian food. Walk to the aquarium, historic Freedom Trail spots, and Boston Public Garden. Or, hop on the T (subway) to see more of the city! 

Salem: Full of great food and eerie history. Tour the House of Seven Gables, have a tea party at Jolie Tea Co, or (our favorite) tour the Peabody-Essex Museum. 

Manchester: Singing beach, Captain Dusty's, and Manchester by the Book are all within half a mile! 

Rockport: Walk (0.9 mi) to Front Beach, downtown Rockport, and Bearskin Neck for stunning ocean views, thriving artist galleries, and seafood. 

Newburyport: As far as old-brick downtowns go, Newburyport is the cutest! You'll have to walk just over a mile from the station. We love coffee dates at Coffee Factory and Plum Island Coffee, or seafood at Loretta.