Boston to Gloucester, MA

The roots of America's heritage run so deep in Boston it would take months to explore just the historical attractions and never experience the city’s other amazing offerings. And if you travel just north of Boston, you find several vibrant communities with their own rich past and unique charm. Cruise to the following three New England towns and discover spectacular scenery, 1600-era buildings, and gourmet eats along the Atlantic coastline.

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Day 1: Portsmouth

Boston to Portsmouth, NH —53 NM

Settled in the early 1600s, Portsmouth remains a working seaport where tugboats nudge ships through the Piscataqua River currents. Its invigorating blend of historic buildings, sidewalk cafes and unique artisan boutiques have earned Portsmouth a Distinctive Destinations title from The National Trust for Historic Preservation. Strawbery Banke Museum in the heart of downtown is an authentic outdoor history museum and a main stop on bike tours of historical neighborhoods. Listen to spooky tales of ghosts, witches and murderers on a self-guided haunted walk to locations in the city’s sordid past including the Old Red Light District and African Burying Grounds.

Chef-owned restaurants and local pubs serving imaginative, locally sourced dishes highlight the culinary scene. There are more restaurant seats than residents! Black Trumpet Bistro & Wine Bar is housed in one of the early 19th century buildings of the old Merchants Row. A shiny patina on the walls is believed to be remnants of linseed oil used for candle making. The wine bar overlooking the water has a curated selection of 12 organic wines by the glass, as well as craft cocktails. The chef, a James Beard award semi-finalist, creates a varied seasonal menu that includes soft shell crab and crispy duck breast.

Started in the early 1800s, Portsmouth’s brewing industry is booming today. Loaded Question, one of many small craft brewers, snugged into the historic west end Button Factory, has a quaint taproom and a spacious outdoor garden.

Wind back the clock in old-world luxury at Wentworth by the Sea, an imposing 19th century resort that commands the island of New Castle, one of New Hampshire’s oldest settlements. Dine on mussels and lobster rolls at Longitudes overlooking the marina.

Where to Dock: Safe Harbor Wentworth by the Sea

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Day 2: Newburyport

Portsmouth to Newburyport, MA — 16NM

Nestled on the shore where the Merrimack River embraces the Atlantic, Newburyport is a travel gem whose unique charm and stunning scenery is anchored in a rich maritime heritage characteristic of coastline communities.

Adorned with seasonal flower baskets, historic Federal mansions line the brick sidewalks leading to the harbor of this enchanting sea captain’s town. Less popular than other classic seacoast stops, the compact downtown has a relaxed pace through quaint little shops, boutiques and art galleries lined up along the main streets or tucked into side alleyways. Amid the upscale shops is long-standing Richdale, a retro convenience store selling a bit of everything including penny candy and imported spirits.

Like many coastal towns, dining options are varied. The Grog Restaurant has a cozy pub ambiance and reliably good fare. Located in a huge (it has more seats than locals) old warehouse, Black Cow adds dishes like pumpkin ravioli, poke bowls and Mussels Cioppino to its standard American menu. For fresh-catch seafood in a lobster shack atmosphere, stop by Bob Lobster to watch the sunset over Plum Island Marsh.

For a once in a lifetime experience, climb 55 winding stairs to an eight-foot diameter room atop Newburyport Lighthouse to experience an unforgettable meal with a view.

Where to Dock: Newburyport Harbor Marina

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Day 3: Gloucester

Newburyport to Gloucester — 15 NM

Cape Ann, the “Other Cape,” offers superb seafood and lovely beaches sans the tourists that crowd Cape Cod. The Cape is home to Rockport, a quaint artists’ colony filled with colorful galleries, and Gloucester, America’s oldest working seaport. The area has a wild and unique nature as much of its rambling 41 square miles of land and water remain undeveloped.

Steeped in fishing lore, Gloucester’s lively waterfront is the homeport of Wicked Tuna, a long-running reality TV series. The show follows a group of salty fishermen whose livelihood is catching bluefin tuna the way it’s been done for centuries—by rod and reel, one fish at a time.

From the famous Man at the Wheel Statue and the Gloucester Fishermen’s Wives Memorial on Western Avenue, stroll eastward along Rogers Street through the historic district.

For “the bread of the fishermen” try Virgilio’s Bakery & Deli which offers 22 sandwiches on 18 different still-warm breads. They’ve been serving the local favorite, the St. Joseph’s Sandwich, since 1961.

Do not pass up Turtle Alley Chocolates whose tag line is, “Life is Short. Sin a Little.” Savor the signature turtles, bold salted caramels with lavender and rosemary, or peanut butter cups with bacon.

The Cape Ann Museum showcases the work of painters, sculptors, and craftspeople including Winslow Homer and Edward Hopper, who have been inspired by the scenery and character of the area.

Just south of the city center, Harbor Loop circles past mounds of lobster traps, a historic dory shop, the Whale Center of New England and Maritime Gloucester, a working waterfront, maritime museum and sea pocket aquarium. The site includes the country’s oldest continuously operated marine railway and a fully restored public pier.

Huge crowds descend on the area on Labor Day weekend for the annual Gloucester Schooner Festival. This capstone to the summer is steeped in maritime heritage and jam-packed with events and opportunities to get up-close and personal with these elegant vessels.

Where to Dock: Cape Ann Marina