Written by Missy Johnston

New England Lighthouse

Many of us travel to learn more about the culture and history of different parts of the world. Compared to other countries, America is still a young, fledgling country, which means it has plenty to offer those interested in exploring its roots. When we look back at America’s beginnings, New England was front and center. The area is brimming with colonial history, so it’s a fabulous choice for those looking to explore the past while also enjoying relaxation and vacation fun.

Experiencing colonial America on a crewed yacht charter cruising in New England is one of the best (and most enjoyable) ways to explore this region. It’s also an opportunity to feel like a real colonist traveling by sea from port to port, just as was often done in colonial times. Not to mention, a private charter yacht cruise through New England is the perfect combination of colonial history and modern-day luxury, with as much beach and water time as you desire mixed in. Some travelers may be close enough to drive to a point of departure for a New England charter yacht trip, making it an even more attractive option. But it’s also easy to book a flight, and well worth it, as New England has plenty to offer to charterers from all over the world.

With so much to see and do in each location, we’ve selected a few highlights (with a bit of colonial history) about each stop to give a sense of all that awaits. Even better, we have also included links to additional resources we’ve compiled. Feel free to dig deeper into the stops that really pique your interest. And, of course, we’re here to help you every step of the way to create a truly personalized New England yacht charter vacation.


boston harbor rowes wharf

Boston Harbor

Board your luxury charter yacht in Boston. The city was founded in 1630 by the Puritans who fled England in pursuit of religious freedom. As a colonial town, it was a major center of activity during Revolutionary times, as the colonists fought for their freedom from British rule. After docking downtown, head ashore to see the many historic sites and explore the culture of the city.

Many of the sites to see in Boston are within walking distance of harbor marinas as colonial Boston was right on the water, making it possible to navigate the city on foot, just as the colonists did so long ago. We recommend taking a walk along the Freedom Trail. Start at the North End (known as “Little Italy”), which was once the center of colonial life. Visit Paul Revere’s home and Bunker Hill. Take a break from history when you get to Faneuil Hall and the old market area near the harbor and visit the many shops, restaurants, and bars—perfect for a souvenir or a classic New England meal.

Another more modern-day experience awaits in Boston Commons. This beautiful city park has a large pond; take a ride in the famous Swan Boats. You don’t want to miss it! There’s also plenty of culture in which to indulge, including the Boston Symphony Orchestra and the Museum of Fine Arts.


Salem, Friendship of Salem, sailing ship and Museum

Salem, Friendship of Salem, Sailing Ship and Museum

How can the infamous Salem Witch Trials not come to mind about this next stop on your New England yacht charter itinerary? This historic town is the next port on your colonial adventure, even though it’s north of Boston. The Salem Witch Trials took place in the 1600’s, and the town has embraced its place in this moment in history. We recommend exploring the Salem Witch Museum to immerse yourself in the full story of this historic event. Featuring life-size sets and narration, you’re sure to feel bewitched.

Speaking of “Bewitched,” be sure to snap a photo or a selfie with television’s beloved Samantha Stevens. There is a statue of Samatha in Salem, where several episodes of the show were filmed. Another great spot to visit is “The House of the Seven Gables,” which was the setting for Nathaniel Hawthorne’s famous novel. A tour here is filled with rich tidbits of Salem history.

There’s still more to see in Salem. The beautiful harbor off Congress Street features a replica of a merchant ship. It was ships such as these that were used in the spice trade, in which Salem merchants played a prominent role in the 18th century and gained great wealth, as seen in the 19th century town houses built along certain wide boulevards in town. Last not but not least, those with a sweet tooth on board must make a quick stop at Ye Olde Pepper Companie on Derby Street. This little gem is the oldest commercial candy store in the country. It’s sinfully delicious!


Rocky Sea shore and cruises in Plymouth, Massachusetts, USA

Plymouth, Massachusetts

Just before the 17.4-mile-long Cape Cod Canal, visit Plymouth. This colonial landmark is often thought of as the spot the Pilgrims first landed in the New World. Although the real location the Pilgrims landed is Provincetown at the very tip of Cape Cod, Plymouth runs deep with colonial heritage and history

Enjoy an interactive experience at Plymouth Plantation, a living museum featuring period actors speaking in the English dialect from the time. There is also an Indian village with period actors. Or, hop aboard the Mayflower II, a replica of the original vessel that carried the Pilgrims across the vast ocean. Another spot to see in town is Sparrow House. Dating back to 1640, this house is now a museum and art gallery.

Plymouth also has many beaches for those looking for some sun and sand. Long Beach is a barrier beach stretching for three miles. Have some fun here, or go for a hike in the 12,000-acre Myles Standish State Forest park. If wildlife sparks your interest, be sure to visit the Tidmarsh Wildlife Sanctuary.

And don’t forget to enjoy the culture. Take in an outdoor concert or live music at one of the local restaurants. There’s also a summer stock theater in a show barn if you’re looking for something a little more rustic.


Main Street Nantucket

Main Street Nantucket

For those who really want to get a sense of what New England colonial life was like, then Nantucket is a must stop on a New England yacht charter trip. This crescent-shaped island is small—just 3.5 miles by 14 miles—but it has been named a National Historic District. That means little has changed over the years. Step ashore and be greeted by seaside cottages and old-fashioned gas lamps lighting up the cobblestone streets at night. It’s a true step back into colonial times. Feeling like a colonist yet?

Nantucket prospered from the whaling industry in the late 1700’s and early 1800’s, but as the whaling ships grew in size, they became too large to access Nantucket’s harbor. After whaling activity declined, it’s almost as if the little island fell asleep, frozen in the 19th century. Today, that same harbor is filled with charter yachts and pleasure boats, coming to enjoy this quaint island and a glimpse back in time.

Nantucket Town is filled with the homes of the wealthy from long ago. Look up at the rooflines to see the famous “Widow’s Walks,” a high perch where wives could watch for whaling ships returning with their seafaring captains to the harbor. To really understand whaling, be sure to visit the Whaling Museum in town.

There are some modern upgrades in town as well, mostly in the form of chic boutiques and art galleries; however, behind all of the colonial buildings and cottages are the old English gardens filled with hydrangeas and other seaside flowers peeking through picket fences. And, of course, don’t forget about the beaches. Swim in the still waters of Nantucket Sound or jump the waves in the Atlantic on the ocean side of the island. The choice is yours as you cruise around the island and explore the beautiful beaches.

Martha’s Vineyard

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Martha’s Vineyard, Oak Bluffs Gingerbread House

“The Vineyard” lies off the southern coast of Cape Cod, and it’s the next stop on your colonial yacht charter itinerary. As the largest island in southern New England, it’s easy to spend a few days exploring this spot during your private charter.

Earlier in its history, Martha’s Vineyard was known for whaling and fishing, but now (as many of us know) it has become quite the hot spot for a summer getaway, especially for royalty, presidents, and the rich and famous. Interestingly, a large portion of the island’s interior is a state forest, but the summer living in the coastal towns is marvelous—and the different harbors are simple to reach via private charter yacht.

Even though the town is associated with the wealthy and elite who vacation here, the vibe is actually quite relaxed. There’s nothing stuffy about the Vineyard. In fact, it’s an ideal island in which to escape, perfect for the lazy days of summer.

The Edgartown Yacht Club (located in the most popular town of the same name) hosts a sailing regatta every summer, which is a fun event if your charter trip happens to coincide at the same time. And Edgartown itself is like taking a walk through history, thanks to its cobblestone streets and historic buildings.

Oak Bluffs is another well-known town. Be sure to visit the religious retreat filled with little Victorian summer cottages covered with gingerbread trim. The protected harbor in this town makes it an ideal spot to anchor overnight. Whether you cruise from harbor to harbor or tour the island by bicycle or bus, there is plenty to choose from while visiting the Vineyard.

Block Island

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Block Island, Southeast Lighthouse

It’s an easy sail from Martha’s Vineyard to Block Island as long as the current through Vineyard Sound is caught in the right direction. A quiet island just 12 miles off the southern coast of Rhode Island, while it may be small in size compared to some of the other stops on your New England yacht charter itinerary, the “Block” is big when it comes to beauty and spectacular views.

Block Island was one of the first locations settled in the early 1600’s, and its lighthouses have welcomed many a maritime visitor over the centuries. Your captain can anchor your charter yacht in the Great Salt Pond, which is also a perfect location for jumping into the water for a swim.

Your captain will have no trouble finding a quiet beach for you and your guests, as there are 17 miles of beaches to choose from. Many have lighthouses, bluffs, and fragrant beach roses, trademarks of New England beaches. We suggest getting your feet sandy at Crescent Beach. This is some of the best beachfront in New England, stretching 2.5 miles along the island’s east coast.

Be sure to visit the Southeast Lighthouse, situated on top of breathtaking Mohegan Bluffs. Go for a hike along part of the 32 miles of nature trails, or rent a bicycle for more exploring. Bicycling is one of the most popular ways to get around the “Block.”


Newport Mansions Rhode Island

Newport Mansions

Now it’s time to sail on to the City-by-the-Sea. While this may be near the end of your colonial adventure, Newport, Rhode Island is by no means the least important colonial port. The city is teaming with maritime and colonial history, and it is the main New England port for yachts. In fact, be sure to check out all of the charter yachts lined up along the docks in the marinas ringing the harbor.

The main harbor in Newport is one of the deepest water harbors on the East coast of the U.S., which made it an important spot for the clipper ship triangular trade with the Caribbean. It is this natural deep water aspect of Newport harbor that made the city a popular and very busy colonial port as clipper ships could sail right up to the wharves and unload. As such, it’s no surprise Newport became a wealthy trading city and one of the most important ports in colonial America where various businesses developed, making candles, distilling rum, printing newspapers and books, and making other goods. In pre-Revolutionary War days, Newport was a more important city than even Boston or New York City.

Bowen's Wharf in Newport

Bowen’s Wharf in Newport , RI

During the Revolutionary War, the British blockaded this important port, bringing all business and life to a standstill. Many of the colonial buildings from that time period remain today, with Newport having the largest stand of colonial buildings still in use today out of any location in the U.S., all of which are still clustered around the harbor. Step ashore and step back into time, once your charter yacht docks in the harbor.

In the late 1800’s and early 1900’s, the wealthy summered in Newport, and the city blossomed with the Gilded Age. The mansions built by these wealthy visitors along the top ridge overlooking the harbor and along the southern coast were quaintly referred to as “Summer Cottages.” An intense social life paying homage to those considered the leaders of society took place in a small section of Newport throughout July and August, with nightly balls that rivalled the events that took place at the height of Versailles in the 1600’s.

Newport Harbor

Newport Harbor

Today, Newport is a main center of New England yachting and yacht charter activity. It has been home to the America’s Cup Races, and may become its home again in the future. Many regattas take place throughout the summer, and a summer station of the New York Yacht Club overlooks the main harbor.

It’s just a short step off your charter yacht to enjoy the variety of shops and restaurants clustered around Newport harbor. Dig into fresh lobster or a clam boil at a local restaurant—or have your private chef create classic New England fare right on board. After a bite to eat or some shopping, we suggest exploring colonial Newport on foot. Perhaps take a guided tour of the grand mansions and imagine yourself living like some of the famous Americans that came before and “summered” in Newport, including Commodore Vanderbilt, the Astors and John F. and Jackie Kennedy.

Beautiful lighthouse by the ocean at sunset

Castle Hill Lighthouse, Newport, RI

One of the biggest advantages of traveling is the immersion in the local culture and history. New England is particularly special in that many locations have preserved much of their colonial heritage. Regardless of where you call home, don’t miss an opportunity to soak up the colonial experience of New England in an unforgettable way—in luxury while enjoying modern-day amenities on your private charter yacht. Contact us with any questions about this colonial yacht charter adventure, so we can help you make your own mark in history.