Day Sail on schooner Adirondack III

Classic Harbor Line

Zerve Seller: BostonSail
Activity #4059

Available Dates & Times Price Duration Tickets Available
All times listed are Eastern time zone
Gift Certificates:


Our classic afternoon day sails are the perfect way to see the sights of Boston Harbor. There is no better way to enjoy the day than sailing aboard the schooner Adirondack III, which is the most elegant sailing excursion you will find in the harbor. Adirondack III is a classically styled 80-foot pilot schooner with long sleek lines. She is smooth and gentle sailing vessel with some speediness to boot.

Within minutes of leaving the dock, you'll forget the distractions of life on land, as you experience the joy of a leisurely sailing cruise. 

Enjoy the historic scenery of Boston Harbor
  • Our first sights, on our day sail, will take you past the Boston Seaport District. There's much to be seen here as the area is featuring many new constructions as well as old. We will point out The Moakley Federal Courthouse at Fan Pier, our World Trade Center, and Harpoon Brewery
  • As our trip extends, we will get into the Inner Harbor Islands. We'll get as close as we can to some of our historical islands including: Castle Island featuring Independence Fort and the Donald McKay Monument, Spectacle Island, and Long Island with the Long Island Head Light House.
Your knowledgeable captain and crew 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! 

Adult beverages are available for purchase while soda and water is complimentary: 
  • Domestic Beer $5.00
  • Local/Micro Brews $5.00   
  • Wine $5.00/glass
Come enjoy the ride, see the sights and have a drink with us!

What Is Not Included?

  • No food is included. Feel free to bring your own picnic!
  • The price of drinks is not included in the cost of your ticket, so please bring extra cash. Water will be provided on board at no cost. 
  • Gratuity is not included in the price of your sail.

Meeting Location

Rowes Wharf--near the Boston Harbor Hotel (Boston, MA) (Exact meeting location details will be provided immediately upon purchase of tickets.)
65 Reviews Rating: 4.6 4.6 out of 5.0
Verified Customer Reviews
Always from real, paying customers
# of Reviews Positive
= Overall
% Positive Average
Last 3 months 0 0 0 = 0 0% 0.0
Last 6 months 0 0 0 = 0 0% 0.0
Last 12 months 43 99 1 = 98 98% 4.6
All 65 156 1 = 155 98% 4.6
65 Reviews
Displaying 1 - 10
Sort by: Date Attended Gender Age Where From Group Type
Rating: 4
relaxing afternoon sail
Mon, Oct 13, 14  3:30 PM Male 60-69 Domestic Tourist(s) Unspecified
The sail aboard the Adirondack III was a relaxing afternoon of sailing around Boston harbor past many interesting sights.

The crew was professional and efficient in their duties, which made for an enjoyable tour.
Rating: 5
Adirondack's last cruise of the season
Mon, Oct 13, 14  3:30 PM Female 60-69 Local Couple on a Date
An unusual warm October day dragged us out for one last summer sail. Beautiful boat inside and out, sailed like a dream. Skilled captain, informative , enthusiastic and well -trained crew made for a perfect day on the water. Have a safe trip heading south avoiding the hurricaine's swells!
Rating: 4
safety concerns
Mon, Oct 13, 14  3:30 PM Female 40-49 International Tourist(s) Family With Children
lifejackets are terrible and staff were unenthusiastic about providing them.
Rating: 5
Great Time
Sun, Oct 12, 14  3:30 PM Female 50-59 Domestic Tourist(s) Family Without Children
We really enjoyed this three hour harbor tour on the schooner. The skipper was very informative and entertaining. The thing that impressed me most was the rescheduling. It was going to be a rainy day on Saturday. I was called on Friday and asked if I would be interested in rescheduling for a Sunday sail or a refund, since the weather wasn't going to be pleasant. I really appreciated this. The woman on the phone was very accommodating to add another member to our party that would be with us on Sunday. This is a great company that is interested in the enjoyment of the guests. Thank you.
Rating: 3
It was not expected SAILING - merely MOTORING.Fake
Sun, Sep 28, 14  3:30 PM Male 50-59 Local Couple on a Date
The whole idea was to really go sailing on a yacht. There was enough wind to get impression OF A LIFETIME. But it was all fake "sailing", just moving using a yacht's engine. They could at least make a short, limited demo on maneuring under sails, to make even slight impression and however limited experience of real sailing. Captain was talking a lot, but was not heard in front of the yacht, he should use megaphone. We missed almost all info on objects around the bay. Few times there was narrowly avoided collision with other boats. There was no respect or care for the passengers, just alcohol and soda instead. This business should be inspected and fined. VERY DISAPPOINTING, VASTE OF TIME AND MONEY. One could go on a speed boat and watch whales, for example - would be better spent time. Ugly lies and liars everywhere. ****, no peace for the wicked.
Rating: 5
Great wait to see Boston from the water
Sun, Sep 28, 14  1:00 PM Female Unspecified Local Couple on a Date
Our second trip on this boat! Love the small group and the information given while sailing. Would definitely recommend.
Rating: 5
Great Activity
Fri, Sep 19, 14  3:30 PM Female 30-39 Unspecified Group of Friends
Small group. The workers were very knowledgeable and friendly.
Rating: 5
Don't miss this trip!
Sun, Sep 14, 14  3:30 PM Female 40-49 Unspecified Unspecified
This was the best thing I did on my trip to Boston. I travel to Boston frequently but had never done this. The 80 ft. schooner is in immaculate shape and the crew is amazing. There was plenty of room and they even had my favorite craft beer, Harpoon UFO White! We went all around the harbor, and I heard things about Boston I'd never heard before. I'd do this again in a heartbeat! Apparently this company has boats in Newport and Key West, so I'll be going on those in the future. Great job guys!!
Rating: 5
Great ride and terrific staff
Mon, Sep 1, 14  3:30 PM Male 50-59 International Tourist(s) Couple on a Date
There isn't much that's wrong with being on a sailboat on a beautiful sunny afternoon. The boat was comfortable and the captain gave us lots of interesting tidbits of information about the area. I was particularly impressed with how the staff helped my wife get on the boat. She was wearing a back brace and when they saw that they sprang into action without me having to ask for assistance. They showed that they knew what they were doing in helping her get on and off the boat easily.

The only knock I have is that we were told to wait for the boast at Dock B. We thought we were at Dock B but the boat was moored a few feet away from where we were and we couldn't see it from where we were sitting. Clearer instructions on where to wait would have helped. They were organized well enough to know they were short two people, so it wasn't a big problem.
Rating: 5
This was one of the best part of our summer.
Sat, Aug 30, 14  3:30 PM Male 60-69 Local Group of Friends
Displaying 1 - 10 of 65
Ratings and Reviews for:
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 $38. However, with a validation from Classic Harbor Line it will be $32. After 5PM weekdays and anytime on weekends the rate is $18, but with a validation it will be $12. 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?
For children between the ages of 3 and 14 you should purchase a reduced-price child ticket. Children ages 2 and younger ride for free, but you’ll still need to enter the appropriate number of infant tickets labeled “Free” when making a purchase. All passengers must have a ticket, regardless of age, so please make sure your entire party is accounted for when booking.
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. If the date you are looking for is not currently listed in the schedule, please check back on this website, or contact Classic Harbor Line by clicking “Contact BostonSail.” Many people also use the “Email a Friend” link to send themselves an email so they can easily return to this page for schedule updates.
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 sails?
Food is not served on the sails. Feel free to bring your own picnic with you on the sail!
How about drinks? Should I bring those?
No, it is illegal for you to bring your own alcohol on board. All of our sails include soda and water, and there will be champagne, wine, and beer 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?
While there is no age limit for the sails, all attendees under 18 must be accompanied by a parent or guardian.
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...) Light weight, plastic ponchos are 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.
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. If you are interested in booking a private sail, please contact us by clicking “Contact BostonSail” to the left of the page.
Is smoking permitted during the sail?
No, smoking is not permitted anywhere on the boat.
Are pets allowed on board?
Unfortunately, pets are not allowed on the sails, other than service dogs
Are gift certificates available for this sail?
Yes, gift certificates are available for the daytime sail on the Schooner Adirondack III, and they make a perfect gift for holidays, birthdays or any other occasion! To purchase a gift certificate for this sail, please click on the "Gift certificates: Purchase" link in the box above.
What if I want the gift certificate emailed to the recipient instead?
That's no problem, either! When you purchase your gift certificate, just select the option to have the certificate emailed directly to the recipient and provide their email address. You'll even be able to decide whether you want the email sent immediately or if you'd prefer to schedule it to be emailed on a future date. (For instance, if you want to buy it today so you don't forget, but you don't want it emailed to the recipient until their special day!)


Refund/Rescheduling Policy

Non-refundable, cannot be rescheduled.
Once purchased, tickets cannot be refunded and cannot be rescheduled because your space is being guaranteed at the event.

Other Policies

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

Classic Harbor Line

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.

Sailing in this schooner is a delight. She moves through the water efficiently and beautifully; we take great pride in sharing her with you.

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. Do not hesitate to ask our crew about the boat or any of the Boston sites.
Please call Zerve at
1 (800) 979-3370
to get more information or
book this activity now
Dismiss this message forever close