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Cape Ann Circumnavigation Sail

Friday, September 10, 2021, 8am-3pm

These full day sails are perfect for those who would like to spend the day sharing sea stories, viewing the diverse land and seascapes of Cape Ann, seeing lighthouses, or just relaxing out on the water. If time allows we will stop in at Rockport for some time ashore or sail into the hole-in the wall at Lane’s Cove. Circumnavigation trips depart from Maritime Gloucester at 8am and return at 3pm (plus or minus) and offer those who come along a chance to really enjoy the Ardelle on an extended trip!

If the weather allows we will circumnavigate Cape, if not, we will head down to some other coastal community or off shore for a whale watch. Bring a picnic lunch and we will provide coffee and donuts and a lot of fun! Adults (16+) only. 

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Music Sail with Daisy Nell & Captain Stan & the Crabgrass Band                                                                                                                                                                            

Friday, September 10, 2021, 6-8pm

Daisy Nell & Captain Stan & the Crabgrass band specialize in traditional and contemporary songs of the sea and shore, with local Cape Ann flavor and lore.

Daisy Nell, native of Essex, MA, mainstay of the shipbuilding industry for over 300 years, brings alive New England's maritime history through traditional songs of the sea. A familiar voice on the North Shore music scene, she is known for her broad repertoire of traditional folk, chanteys, and contemporary songs. 

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Music Sails with Headlands


Headlands, featuring John Rockwell, Amy Rich and Eric Wilson all of Rockport, look forward to entertaining you with their musical renditions and powerful vocals on their maiden voyage aboard the Ardelle. The talented fiddle player, Melinda Kerwin, of the Kelly Girls, will play a few tunes with Headlands which always proves to be a musical experience not to be missed. Their sweet harmonies accentuate their song choices ranging from roots and Americana to a little bit of country. They love making music together and like nothing more than sharing their joy with music appreciators. 

Seamanship Sunday Mornings

Next session TBD

Through these 3-hour training sessions participants (18+) will have the opportunity to learn, practice and fine-tune a variety of seamanship skills. Each session will begin with a mug-up and introduction to the day's skill and weather. The vessel will then get underway, complete and log a safety drill and then participants will take turns practicing the skills of the day.

Please see the complete course description here. Each session is $80 or sign up for all 4 for $60/sessions.

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3rd of July Fireworks Cruise


Enjoy the spectacular Gloucester Fireworks from a front row seat aboard the Schooner Ardelle!


Blackburn Challenge Race Finish


Join us as we greet the Blackburn Challenge rowers as they approach the finish line in Gloucester Harbor! 

Named for Gloucester legend, Howard Blackburn, the Blackburn Challenge is a twenty mile rowing race that circumnavigates Cape Ann. Cheer on the rowers as they enter the final stretch! This sail provides a great opportunity to photograph the race finish from the water while enjoying the beautiful scenery of Gloucester Harbor.



Mother's Day Sail!  


Happy Mother's Day! Mothers sail free when accompanied by the purchaser of one full priced ticket. Limit one mom per full priced ticket purchase. Cannot be combined with other offers/discounts.

Father's Day Sails


Gloucester Harbor History Sails with Local Historian Justin Demetri

Wednesday, August 18, 2021, 6-8pm

Join us for an evening of sea stories and relaxation as we explore the history of Gloucester's iconic schooners and the International Fishermen's Cup Races with local historian and author Justin Demetri. 

Growing up "Down the Fort" in one of the many families that comprised Gloucester's Italian fishing fleet, Justin spent his childhood among the fishermen, the boats and the wharves. Justin's friendship with author and historian Joseph E. Garland sparked his love of writing, and appreciation for the special place he still calls home.

Justin holds a degree in Cultural Anthropology from the University of Massachusetts/Boston and is the Historian at Maritime Gloucester. 

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Happy Father's Day! Fathers sail free when accompanied by the purchaser of one full priced ticket. Limit one dad per full priced ticket purchase. Cannot be combined with other offers/discounts.


Music Sail with Down Home Swing

Friday, August 27, 6-8pm

DOWN HOME SWING delivers the finest in jazz, blues, country, and so much more, in a heartfelt and rousing way. Their act features traditional and contemporary tunes, thrilling harmonies, and expert picking, delivered with flair and enthusiasm. DOWN HOME SWING is Jay & Laurie and Chick & Ellen - two married couples, four professional musicians, friends for many years. When they began performing together as a quartet, their sound came together quickly, fed by their abiding friendship and stellar musicianship.  


Music Sail with Marina Evans

Wednesday, September 1, 2021, 6-8pm

A brave performer, composer, and traveler, singer/songwriter Marina Evans has traveled around the world with her music. Combining her background as a jazz singer with traditional folk americana and a pop sheen, Marina has refined her sound over many miles (and years!) on the road, the stage, and in the studio. A Cape Ann native, she now divides her time between her hometown and her adopted home of Florence, Italy, where she lives, writes, and records with her husband, producer, and musical partner Bernardo Baglioni. She returns to New England this summer for a limited number of solo shows where she will perform songs off her latest record, “Tide and Stars,” as well as debut some brand new original material. Visit for concerts, music, videos, and more.  


Schooner Challenge

Thursday, September 2, 2021, 5:30-7:30pm

Help us raise anchor, set the sails, and best our rivals! We will be joined in the Challenge by the schooners Thomas E. Lannon, Alert, Redbird, Bald Eagle and others. 

This will be a great opportunity to take photos of visiting schooners as we welcome them to Gloucester for Schooner Festival Weekend!


Greet the Fleet

Friday, September 3, 2021, 1:00-3:00pm

Join us as we welcome visting schooners to Gloucester Harbor for the 2019 Gloucester Schooner Festival!

A great opportunity for  schooner fanatics and photographers!





Heritage Day 1-Hour Sails!

Saturday, September 4, 2021, 10:45-4:45pm

The best deal of the weekend! Join us for a one hour sail in Gloucester Harbor to see the visiting schooners during Maritime Gloucester's annual Heritage Day Celebration!  Tickets are $20!

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Gloucester Schooner Festival Fireworks Sail

Saturday, September 4, 2021

Enjoy the spectacular Gloucester Schooner Festival Fireworks from a front row seat aboard the Schooner Ardelle!

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Gloucester Schooner Festival Parade of Sails 

Sunday, September 5, 2021

Join us as we participate with over 30 Schooners in the Gloucester Schooner Festival Parade of Sail! A great opportunity to see the schooners up close and photograph this spectacular event!

Sail is 2-hours and does not include the Schooner Race.