Boston Yacht Charters

Rich in history and with a decidedly cosmopolitan flair, Boston is the crown jewel of New England. And during the summer months, this Shining City Upon a Hill is the region’s sailing hub. Crewed charters depart Boston Harbor, allowing visitors to explore the splendor and natural beauty of Massachusetts.

Boston offers quick access to yachting hotspots like Nantucket, Martha’s Vineyard, the Elizabeth Islands, and Newport, RI, (through the Cape Cod Canal), and the city is a key hub for Cape Cod yacht charters. Boston charters offer guests an endless array of itinerary options.

Whale watch in Massachusetts Bay, where grey whales and humpbacks spend their summers. Explore the historic villages of the Bay’s South and North Shores, like Plymouth or Salem. Or take a shore break and explore Boston’s museums, world-class dining scene, and cultural hubs. Bottom line: A yacht charter in Boston opens a world of possibilities to explore and experience New England’s natural, cultural and historical sights and sounds.

Boston Yacht Charter Highlights

  • Hip, upscale restaurants, and excellent food
  • World-class museums, aquariums, and tours
  • Access to all of New England
  • High-end boutiques and shopping
  • Sportfishing in nearby Cape Cod Bay
  • Whale watching in Massachusetts Bay
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Boston Yachting Season

Boston’s yachting season mirrors that of New England; it wakes up in early spring, but doesn’t hit its stride until mid-summer. July and August are the region’s busiest months for crewed yacht charters, with the season stretching into late September.

Throughout the summer and fall, Boston hosts a wide range of yachting events, including regattas and boat shows. Peak season runs from the Fourth of July until late August, and demand for luxury charters is also higher around major events, including the nearby Newport International Boat Show.

Cruising Conditions

Boston is blessed with pleasant spring and summer weather. In July and August temperatures hover in the 70s and 80s, with plenty of cooling winds.

The region is a sailor’s dream. Thanks to the relatively sheltered waters of Massachusetts Bay, Cape Cod Bay, Nantucket Sound and Buzzards Bay, Boston charters are generally met with calm, smooth sailing conditions.

Boston harbor

Boston Yacht Charters: Things to See & Do

Whether you prefer to stay close to beautiful Boston Harbor and explore the city or seek adventure on the high seas, Boston charters are full of excitement. Top attractions and must-do activities include:

See the Red Sox at Fenway

Legendary Fenway Park is the oldest stadium in baseball and has been hosting the Red Sox every summer since 1912. Taking in a game at Fenway is a Boston bucket list experience. One tip: Plan for a pub crawl before or after the game. You’ll find numerous Irish pubs in the neighborhood.

Indulge in Boston’s Dining Scene

Boston is heaven for foodies. And all across the city, you’ll find a wide range of dining experiences, from the exquisite 3 Michelin-star cuisine at Menton, to the lobster roll shacks like Yankee Lobster. Throughout the region, you’ll find the best of the best in seafood: lobster, clam chowder, fish and chips, and clam bakes.

Take a Walk Through History

Boston’s Freedom Trail is a network of churches, museums, and historical markers that tell the history of the American Revolution. From the Old State House, where the Declaration of Independence before it was signed, to Paul Revere’s house, a walk along the trail brings the city’s history to life. You’ll find a variety of self-guided or guided options.

Shop Boston’s Upmarket Boutiques

Boston offers a wide range of markets and high streets to explore. Try Newbury Street – the so-called East Coast Rodeo Drive – for designer boutiques and high-end restaurants. Other options include Faneuil Hall and Quincy Market, for an eclectic selection, or Copley Place for designer fashions.

Tour Boston’s World-Class Museums

Boston is home to some of the best museums on the East Coast. Whether you’re a history buff, or want to take in the arts, you’ll find a range of options. For natural history, visit the Boston Aquarium or the Harvard Museum of Natural History. Try the Institute of Contemporary Art or the Museum of Fine Arts, Boston if you fancy the arts. And the Boston Tea Party Ships & Museum is a great stop for history.

Take to the Beaches of Massachusetts Bay

Explore the waters and beaches around Boston Harbor. You’ll find many quintessential New England beaches, with their dunes and wind-swept white sand. Singing Beach of Manchester-by-the-Sea, Spectacle Island (just outside of Boston Harbor), and Head of the Meadow in Truro are all must-see beaches.

Whale Watching in Cape Cod Bay

Whale watching season in Boston runs from mid-March through October, with many popular feeding grounds north of the city along the North Shore of Massachusetts Bay. In particular, explore the waters of the Stellwagen Bank, a protected area, where humpback and finback whales are a common sight.

Explore Nantucket, Martha’s Vineyard, and the Elizabeth Islands

The Cape Cod Canal connects Boston to all of New England’s world-renowned sailing destinations. As such, many Boston yacht charter itineraries include stops in Nantucket or Martha’s Vineyard, as well as in the Elizabeth Islands. Newport is another must-stop on a Boston yacht charter.

Book Your Boston Yacht Charter

Set sail from Boston on a private crewed yacht charter. Boston is an ideal sailing hub for New England; explore all of the region’s revered sailing grounds on a Boston charter, including Nantucket, Martha’s Vineyard, the North Shore of Massachusetts Bay, Cape Cod and Newport. Book a boat rental with Worldwide Boat today.