Discover Historic New England

USS Constitution
Donovan Reeves, Unsplash

It’s time to go back to where it all began. Visit New England to be immersed in American history, from the arrival of the Puritans in 1620, through the Revolutionary War, and beyond. Discover some of America’s “firsts” when you complete the New England History Itinerary, brought to you by Ocean Havens.

Start your journey in Provincetown, the harbor in which the Mayflower Compact was signed, and step foot in beautiful Cape Cod. Spend some time exploring historic landmarks before traveling into Boston Harbor and visit landmarks that played a vital role in the nation’s founding. End your journey in Portland, Maine - home to its own Freedom Trail and historic sites with a rich maritime background. 

Pilgrim Monument overlooking Provincetown Marina

Day One: Pilgrim Monument and Provincetown Museum

Where to stay: Provincetown Marina

Built to commemorate the Pilgrim’s landing in 1620, climb to the top of the Pilgrim Monument and tour the museum to learn more about the history of the nation’s beginning!

While in the neighborhood, spend the day at Race Point Beach, sign up for an Art’s Dune Tour, shop the stores and galleries on Commercial Street, and grab a bite to eat at the Lobster Pot.

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MacMillan Pier

Day Two: MacMillan Pier

Where to stay: Provincetown Marina

Named after Naval Reserve Rear Admiral Donald B. MacMillan, who made 30 voyages to the Arctic over the course of his 46 years in the Navy. From what he learned on his expeditions, MacMillan was able to produce dictionaries and maps for languages and areas previously unknown.

While you are there, visit the Atlantic White Shark Conservancy, an exciting museum for people of all ages to learn about the magnificent apex predators. MacMillan Pier is also the place to climb aboard a whale watch!

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Long Point Light Station

Day Three: Long Point Light Station

Where to stay: Provincetown Marina

Make your way to the very tip of Cape Cod! Built in 1827, the Long Point Light Station has long guided mariners into Provincetown Harbor. The light house has undergone renovations over the years and was automated in 1952. 

While you’re there, visit Long Point Beach. Take some time to browse the Provincetown Art Association and Museum, with plenty of exhibitions planned for this summer, there is always something new and interesting to see.


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USS Constitution
Donovan Reeves, Unsplash

Day Four: USS Constitution

Where to stay: Charlestown Marina

Nicknamed “Old Ironsides,” the USS Constitution is the oldest commissioned naval ship still afloat. Visit the museum to learn more about her history and climb on board to be immersed in American History. 

While in the neighborhood, visit the Boston Museum of Science, or catch a game or concert at TD Garden.

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Paul Revere Statue

Day Five: Paul Revere House

Where to stay: Boston Yacht Haven Inn & Marina

Before making his famous “midnight ride,” Paul Revere lived in this Boston home. Visit the museum to learn about the man who made history, and the true story that unfolded April 18th, 1775.

While in the neighborhood, visit the New England Aquarium, Union Oyster House, the Rose Kennedy Greenway, and Faneuil Hall.

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Boston Tea Party Museum
Jonathan Sherman, Unsplash

Day Six: Boston Tea Party Museum

Where to stay: Fan Pier Marina

Throw tea into the harbor! At the Boston Tea Party Museum, you will have the opportunity to climb aboard an 18th century replica vessel, just like the revolutionaries did back in 1773.

While in the neighborhood, browse the Institute of Contemporary Art, swing on the Lawn on D, and find fun at King’s Entertainment or Puttshack.

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Harvard University
Somesh Kesarla Suresh, Unsplash

Day Seven: Harvard University

Where to stay: Boston Yacht Haven Inn & Marina

As the first college established in America, Harvard is famous for its illustrious history and notable alumni. A short cab ride or ride on Boston’s public transit system, known as “the T,” will bring you ride to Harvard Square. Take a tour of the campus, and be sure to snap a photo with the John Harvard statue while you are there!

While in the neighborhood, visit the Art or Natural History museums, see a show at The Sinclair, and grab dinner and drinks at Felipe’s Taqueria (their rooftop is open for the summer!).

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Portland, Maine

Day Eight: The Portland Observatory

Where to Stay: Fore Points Marina

As the only historic maritime signal station that still exists in the United States, the Portland Observatory is bound to catch the eye of anyone arriving in the harbor. What started out as a subscription for owners to be notified when their ships arrived has turned into a National Landmark and popular attraction in Portland. Climb to the top and experience the incredible view!

While in the neighborhood, visit the Victoria Mansion and tour its extraordinary interior design, or take a short ride to the Maine Classic Car Museum to learn more about automobile history and see the classic cars on display.

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Maine Lobstering

Day Nine: Maine Lobstering

Where to Stay: Fore Points Marina

An industry with an illustrious history, learn more about the lives of Maine Lobstermen aboard a lobstering tour. You are bound to encounter lots of marine life and be met with stunning views along the coast.

While cruising around Casco Bay, take an excursion to Fort Gorges. This former military fort has been transformed into a beautiful park and makes a great place to explore and spend the day. When you return to land, take a short ride to the LL Bean Flagship Store and be sure to snap a photo in front of the iconic Bean Boot!

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Portland Freedom Trail

Day Ten: Portland Freedom Trail

Where to Stay: Fore Points Marina

As you wrap up your visit to Portland, set out to tour sites along the historic Portland Freedom Trail. Some highlights include the Secondhand Clothing Store of Lloyd Scott, Franklin Street Wharf, and the Friends Meeting House.

While in the neighborhood, grab a bite to eat at TWELVE after working up an appetite exploring the freedom trail.  This building is over 150 years old, and while it was originally a pattern storehouse, it was disassembled and rebuilt in a new waterfront location to become the fine dining location it is today. Also visit the home of famous poet, Henry Wadsworth Longfellow.

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Map of Historic New England Itinerary

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