Windjammer and Sailing Cruises in Massachusetts

schooner passes Ten Pound Island light

Enjoy sailing and  the natural beauty that surrounds you, while looking for lighthouses? Most sailing adventures and cruises are provided either along Buzzards Bay, outlining Cape Cod, between Hyannis Harbor on Cape Cod out to Martha's Vineyard or Nantucket Island on longer excursions, or out of Provincetown Harbor on the tip of Cape Cod. Boston Harbor provides quite an area region for sailing, and up north visitors can find sailing tours around Cape Ann out of Gloucester Harbor. 

Some of these sailing cruises are aboard traditional sailing vessels and authentic windjammers, also known as "tall ships" in Massachusetts. Sailing cruises mentioned below usually offer many types of excursions. Some of these vessels participate in various regional events, like the Gloucester Schooner Festival, while others provide 2-hour day and sunset sails for guests. These boats will usually pass by various lighthouses, although wind direction and weather is always a major factor in New England in determining the daily route.

Liberté, The Schooner
Three-masted sailing schooner departs 3 times a day, seven days a week, from Falmouth Harbor; sailing conditions depend on route. Sailing may include around Woods Hole, Elizabeth Islands, or out to Martha's Vineyard, around Oak Bluffs and Vineyard Haven. Depending on weather conditions, may be able to view Nobska Light, East Chop Light, West Chop Light, and possibly Tarpaulin Cove Light.

227 Clinton Avenue
Falmouth, MA 02540
Phone: (508) 524-9121
E-mail: Theliberte@gmail.com

 

Bay Spirit Tours on a Catamaran
The Bay Spirit is a 63-foot catamaran that was originally built in Florida, and was used by the Florida Aquarium for dolphin watching tours. Today she provides guests lighthouse sailing tours, sunset cruises, music cruises, and sailing charters around Hyannis Harbor. The Lighthouse Harbor Tour is a narrated cruise that passes by Point Gammon Light on Great Island, (weather dependent), and passes by Hyannis Harbor Light. They cruise through the old Hyannis Harbor in Hyannisport where visitors can catch a glimpse of the Kennedy Compound. For specialized charters, the Bay Breeze is a 45-foot Lock Crowther designed catamaran with an extra wide deck and can carry up to 25 passengers.

Slip # 1, 180 Ocean Street1
Hyannis, MA 0260
Phone: 508-771-0107
Email: info@bayspirittours.com

 

Schooner Bay Lady II
Afternoon and sunset sailing excursions from Provincetown Harbor to Cape Cod Bay may pass by Long Point Light and possibly Wood End Light. Provincetown, on the tip of Cape Cod, is one of the few places on the East Coast where guests can view the sun setting in the West over the water.

20 Berry Lane
Provincetown, Mass. 02657
Phone: (508) 487-9308
info@sailcapecod.com

 

 

Liberty Fleet of Tall Ships
Built in 1982, the 67-foot Schooner Liberty Star provides up to 42 guests with 2-hour public themed sails that include Boston Harbor Day Sail, Boston Harbor Sunset Sail, and Pastries and Prosecco, along with events like Fourth of July Fireworks Cruise, Harborfest Fireworks Cruise, and the Annual USS Constitution Turnaround Sail. Boston Harbor lighthouses may be viewed depending on weather and route. Private charters are also available.

Fan Pier Marina, Boston, MA
Boston, MA 02129
Phone: (617) 742-0333
Email: liberty@libertyfleet.com

 

Sailing Schooner Fame
Replica of the first American privateer sailing schooner during the War of 1812. Daytime and sunset 2-hour sails out of Salem Harbor. Depending on weather, may pass by Derby Wharf Light and Fort Pickering Lighthouse, and possibly out to Hospital Point Lighthouse.

Pickering Wharf Marina
86 Wharf Street, Salem, MA 01970
Phone (978) 729-7600
schoonerfame@gmail.com

 

schooner passes Hammond Castle in northern Massachusetts

Schooner Thomas E. Lannon
This 2-masted 65-foot fishing schooner (90-feet overall) is covered in hardwoods like white oak and elegant mahogany, with masts made of Douglas fir. She has mostly 2-hour public sails, which include sunset, music, star gazing, moonlight, and fireworks cruises, along with Tuesday Special and Sunday morning sailing cruises. Charters are also available. Coming out of Gloucester Harbor, visitors may be able to see Ten Pound Island Light and Eastern Point Light.

63R Rogers Street Rte. 127, Gloucester, MA 01930
Phone: (978) 281-6634
Email: info@schooner.org

 

Books to Explore

book of the rise and demise of the largest sailing ships

This book is available in paperback, hardcover, and as an eBook for all devices.

my ebook on apple books

The Rise and Demise of the Largest Sailing Ships:
Stories of the Six and Seven-Masted Coal Schooners of New England

In the early 1900s, New England shipbuilders constructed the world’s largest sailing ships amid social and political reforms. These giants of sail were built to carry massive quantities of coal and building supplies and measured longer than a football field! These true stories include competitions, accidents, battling destructive storms, acts of heroism, and their final voyages.

 

 

Lighthouses and Coastal Attractions of Southern New England:
Connecticut, Rhode Island, and Massachusetts

This resourceful book provides special human interest stories from each of the 92 lighthouses along the southern coast, with plenty of indoor and outdoor coastal attractions and tours, and helpful contact info for your vacation plans. You'll also find info on haunted lighthouses, sailing, whindjamming, and whale watching tours among other of events along the coast.

Look inside!

book of lighthouses, tours, attractions, and contact information in southern New England

 

 

Lighthouses and Coastal Attractions of Northern New England:
New Hampshire, Maine, and Vermont

This book provides human interest stories from each of the 76 lighthouses in northern New England, along with plenty of coastal attractions and tours near each beacon, and contact info to plan your special trips.

Look inside!

book northern New England lighthouses and local coastal attractions

 

 

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