easy
2–3 hours
Suitable for all fitness levels; comfortable seating and gentle movement on the schooner.
Discover Boston’s maritime history on the Schooner Adirondack Oyster Sail. It’s a unique experience combining scenic harbor views with fascinating stories of oyster harvesting and naval traditions. Perfect for history lovers and outdoor adventurers alike!
Classic Day Sail with Freshly Shucked Oysters
Experience the ultimate Boston Harbor adventure with our Sailing & Oyster Tour! Sail past iconic landmarks while savoring freshly shucked oysters and shrimp, paired with wine. Enjoy wildlife spotting and learn about the rich history of oysters in Boston. This unique blend of sailing and culinary delight promises unforgettable memories!
To participate in the tasting you must purchase "A tasting" in the extras of the purchase page.
Included with the tasting:
In addition to the tasting:
Your knowledgeable captain, crew, and Harpoon Brewery representative are always ready to answer your questions about the sights and history of Boston Harbor and its surrounding areas. From interesting facts to old-time legends, the maritime world of Boston has many great stories to offer. Ask them anything you'd like to know!
Come see the sites and enjoy a beer tasting while sailing!
Feel free to join us on the sail even if you do not wish to participate in the tasting. Please let us know if you are not interested in the beer pairings when purchasing tickets.
Light bites will be available aboard, but please feel free to bring your own picnic!
The beer tasting is not included with your ticket. To participate in the beer tasting you must purchase "A Tasting" in extras section of the purchase page or notify us in the message to sellers that wish to purchase a tasting when you arrive.
Domestic Beer $6.00
Local/Micro Brews $6.00
Wine $6.00/glass
Water and soda will be provided on board at no cost.
Gratuity is not included in the price of your sail.
Do sails sell out frequently?
Sails often sell out, and are rarely open for booking more than a week in advance. Check the website or call the week of the date you would like to attend to check availability for public trips and to book as early as possible.
What happens if the sail is sold out?
Unfortunately, we do not have a wait list for our sails, so please book well in advance.
Is there parking and how much is it?
Limited metered parking can be found around Rowes Wharf. Regular daily rate at the Boston Harbor Hotel is $42. However, with a validation from Classic Harbor Line it will be $36. After 5PM weekdays and anytime on weekends the rate is $20, but with a validation it will be $14. Please be sure to ask our ticket representative for a validation when you check-in.
What type of ticket should I buy if I'm bringing a very young child?
Sorry, children are not allowed on this event. Only adults 21 and older. On that note, please be sure to bring valid identification such as: a driver's license or passport to back up your age.
Why doesn't the schedule list weekdays for more than the next couple of weeks?
The schooners are a very popular choice for private charter sailing, so weekdays are added as they become available for the public, which may not be until just a week or two before the sail date.
What exactly do we see on the sail?
While each sail may differ due to wind and other conditions, we try to follow our regular route, which involves heading East out of Harbor, passing the financial district and making our way towards the islands that dot Boston Harbor and then coming back to Rowes Wharf and taking in all that the Boston Skyline has to offer.
Is food served during the sail?
This sail will feature some small bites - either a cheese and cracker platter or a platter from one our fabulous neighborhood restaurants. The platters will only provide you with a small snack. You are welcome to bring your own picnic with you or we recommend eating before your excursion.
How about drinks? Should I bring those?
No, it is illegal for you to bring your own alcohol on board. If you wish to participate in be beer tastings please purchase the Tasting extra. The tasting extra includes 5 4-oz beer tastings from Harpoon Brewery. You may purchase additional beers after the tasting for $5 each. we will also have wine and champagne available for purchase.
Is the Schooner Adirondack III safe?
Absolutely. The Schooner Adirondack III is a safe and gentle vessel. Along with your captain, there is a minimum of two crew members on every sail to make sure you feel comfortable and at home on the water. We are stocked with water, beverages, blankets, pillows, and life jackets, should you feel you need one. There IS also private marine head (bathroom) below.
How steady is the sailing? Am I likely to get seasick?
The Schooner Adirondack III is a steady, gentle vessel. It is very rare for our guests to become seasick. While most people do not experience any sea sickness on the schooner, you may want to consider light medication if you normally take it for motion sickness. We cannot officially advise you to take any medication, however.
Is there a bathroom on the boat?
Yes, the boat is equipped with a bathroom that is accessible at all times. We call them "marine heads" and they are unlike the bathrooms you use at home. Using a marine head involves pumping, and there are simple directions posted in the bathroom on how to use it.
Is there an age limit for these sails?
Yes, you must be 21 or older to attend.
Can I stow anything (eg, my briefcase) during the sail?
There is an area below deck where you may store your belongings. Please keep in mind that this area is not guarded, so we cannot take responsibility for any broken, lost or missing items. But we have not had any problems with items being left on prior sails.
Where does the sail finish?
Our sails will end at the same pier from which they departed, Rowes Wharf.
Can I get a refund or reschedule my tickets after buying them?
Because we are guaranteeing your space on the sail, tickets cannot be refunded or rescheduled once purchased.
Do you ever cancel sails due to bad weather?
The sail usually runs in light rain and other moderate weather situations. The only time we cancel a trip is in the event of severe or unsafe weather conditions. Our captains monitor the radar to watch fronts and cells in the area on days when inclement weather is possible. Cancellations are made on the day of the sail, by the captain, up to one hour prior to sail time. If you have purchased tickets for a sail that is canceled, you will have the opportunity to reschedule your tickets (subject to availability), receive credit towards a future event, or get a refund.
What happens if it starts raining when we're out on our sail?
Don't worry, we won't melt! Trips with a little wetness have proven to be some of the most memorable bonding experiences for our guests. (This all depends on attitude of course...) We have ankle-length, button-down raincoats available for all of our guests aboard the Adirondack III in the case we are caught in a rain-shower.
Is gratuity included in the price of the sail?
Gratuity is not included in the price of the sail. Parties of 12 or more will be contacted directly by Classic Harbor Line within 48 hours of purchasing tickets to provide credit card information for an additional charge of 18% gratuity.
Are the schooners handicap accessible?
No, unfortunately the schooners are not wheelchair-accessible.
Can I book a private charter sail?
Yes, private sails on the Schooner Adirondack III can be a unique and elegant event for your group.
Are pets allowed on board?
Unfortunately, pets are not allowed on the sails, other than service dogs.
Is smoking permitted during the sail?
No, smoking is not permitted anywhere on the boat.
Are gift certificates available for this sail?
Unfortunately, gift certificates are not available for the beer tasting. However, gift certificates are available for the Day Sail and Sunset Sail on the Schooner Adirondack III, and they make a perfect gift for holidays, birthdays or any other occasion!
Non-refundable and cannot be rescheduled Once purchased, tickets cannot be refunded and cannot be rescheduled because your space is being guaranteed at the event.
All participants are required to have tickets for this event. According to U.S. Coast Guard capacity rules, all passengers including infants and toddlers must have a ticket.
Activity may be canceled due to severe weather The activity usually runs in light rain and other moderate weather conditions, but the seller may cancel the activity up to an hour before the start time in the event of severe or unsafe weather conditions. If the seller cancels the event, ticket-holders will be allowed to reschedule tickets (subject to availability), receive a credit for a future event, or receive a refund.
Parties of 12 or more will be contacted for an additional gratuity charge of 15% Classic Harbor Line will contact you directly within 48 hours of your purchase to take your credit card information for the additional charge. You must be reachable at the telephone number and email you provided.
Beverages and Coolers Outside adult beverage and coolers are not allowed aboard. Please bring valid identification with you. Identification is checked prior to boarding for guests interested in an adult beverage.
Check-In Upon arrival to our location, please check–in with our ticket representative inside the ferry terminal to receive boarding passes.
Classic Harbor Line’s Adirondack III features teak decks, mahogany-trimmings, and just under 2,000 square feet of canvas to escort you through Boston’s historic harbor!
Though it is a light and lively sailing vessel, it is also quite comfortable, with ample deck space and seating for up to 42. It was designed and built by Scarano Boat Building of Albany, NY for taking groups of people on spectacular sightseeing adventures.
The Adirondack III is operated by Coast Guard-certified captains and an extremely friendly and talented crew. Our crew is known for their amazing hospitality, and are professionally trained and experienced in sailing our vessels well and safely.
We started the Harpoon Brewery in 1986 because - like today--we loved beer and wanted more quality choices. There was only on problem: we were beer lovers, not brewers. We knew what we wanted to drink, but we needed some help actually brewing it. So we enlisted out first brewer, took over some warehouse space on the Boston waterfront, and began introducing fresh, local craft beer to Boston drinkers. We tried to do it in a way that captured the spirit of fun that had brought us to beer in the first place. From the waterhouse, surrounded by fish companies on the docks of South Boston (neighboring what is now the Seaport District), we couldn't imagine that craft brewing would become what it has today. We look forward to sharing a pint with you!
Get to the dock at least 15 minutes early to secure a good spot and enjoy the harbor scenery before departure.
Weather on the water can be unpredictable; wear layers and bring a light jacket even in summer.
Capture stunning views of Boston Harbor and take memorable photos of the schooner and city skyline.
Tours can fill up quickly during peak seasons, so reserve your spot early to avoid disappointment.
Boston’s oyster industry was once a vital part of the local economy, with oyster beds flourishing in the harbor since the 19th century.
Efforts are ongoing to restore native oyster populations and maintain clean harbor waters, supporting local ecosystems.
Protect yourself from sun exposure during prolonged time on the water.
summer specific
Stay dry and comfortable if weather turns rainy or windy.
spring|fall|winter specific
Wear non-slip shoes suitable for being on a boat.
Capture memorable views of Boston Harbor and the schooner.