Welcome Aboard!
Picture yourself relaxing on the deck of this beautiful 65- foot schooner as she sails out of Gloucester harbor on a light southwesterly breeze.
Join us for a sail and get a taste for what it was like to sail on a fishing schooner a hundred years ago. Help the crew raise the sails, or just sit back and take in the sights and sounds of Gloucester’s coastline.
“Such an easy, relaxing, and incredibly worthwhile experience! The crew is very friendly and will take great care of you while you’re on board. This was our first visit to Gloucester together, and I’m glad we were able to share this experience with family.”
– Noah S
Specialty Sails & Deals
In addition to our one and a half-hour public sails, we also offer several “Specialty Sails”. Some are longer and offer dessert or music. Some offer pricing specials.
Congratulations to Captain Heath, winner of the Destination Excellence Frontline Hospitality Award from the North of Boston CVB! 🎉
Thank you to everyone who voted, and to the North of Boston CVB for the nomination.
This award celebrates the frontline hospitality rock stars who bring their best to every interaction and go above and beyond for visitors to the North of Boston. After 30 years in the business, that’s Captain Heath to a T. Whether he’s sharing his deep knowledge of the water, sailing, and Gloucester’s waterfront history, cracking a joke (he’s a pretty funny guy), or just making sure everyone has the best day possible on the water, he does it with warmth and a smile. He truly cares about people, and it shows.
We’re so proud of you, Cap. Well deserved! ⚓ @visitnorthofboston
Captain Heath has been nominated for the North of Boston Frontline Hospitality Award! This award recognizes frontline hospitality rock stars — the people who bring their absolute best customer service skills to every interaction, and regularly go above and beyond to provide an excellent experience to North of Boston visitors. He works tirelessly to give visitors the best experience possible on the water, while keeping everyone safe and entertained! Help us give him the recognition he deserves — a vote takes just a few seconds. ⛵️Link in bio!
Our time at the Sail Boston 250 Tall Ships event was a blast! What a privilege it was to be in Boston Harbor with these magnificent vessels from all around the world for the week. Thank you to Sail Boston for hosting us, and thanks to our amazing crew who worked so hard this past week to give everyone the experience of a lifetime! #sailboston2026 #sailing⛵️ #sailboston
Happy 250th America! #4thofjuly
Boothbay Windjammer Days 2026 was so much fun! Shoutout to @friendsofwindjammerdays for putting on a really great event, as always. #sailing #windjammerdays #boothbay
Gift Certificates
Gift Certificates are limited to the terms and conditions included with the certificate. Per Massachusetts State Law, Gift Certificates are good for 7 years from the issuance date.