Sunset Sail on schooner Adirondack III

Classic Harbor Line

Zerve Seller: BostonSail
Activity #4092

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


Experience a beautiful Boston Harbor sunset on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. You will be aboard the most elegant sailing yacht in town, Adirondack III, a classically styled, 80-foot pilot schooner. 
Adirondack III is the fastest and most elegant schooner in Boston Harbor. She offers a smooth and gentle sailing experience to her passengers as well as top notch customer service by her captain and crew. Enjoy a comfortable and relaxing ride for you and your loved ones.

Within minutes of leaving the dock, you'll forget the distractions of life on land, as you experience the ambiance of a sunset sailing cruise aboard a stellar vessel.

Enjoy the historic scenery of Boston Harbor
  • Our first sights, on our sunset 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 our World Trade Center and the Harpoon Brewery. 
  • Also on our route, we will sail past The Moakley Federal Courthouse at Fan Pier
  • 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 and soda 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.)
113 Reviews Rating: 4.7 4.7 out of 5.0
Verified Customer Reviews
Always from real, paying customers
# of Reviews Positive
= Overall
% Positive Average
Last 3 months 35 90 0 = 90 100% 4.8
Last 6 months 59 151 1 = 150 98% 4.7
Last 12 months 59 151 1 = 150 98% 4.7
All 113 288 1 = 287 99% 4.8
113 Reviews
Displaying 1 - 10
Sort by: Date Attended Gender Age Where From Group Type
Rating: 5
Perfect end to a great vacation.
Wed, Oct 7  5:00 PM Female 50-59 Domestic Tourist(s) Family Without Children
We thoroughly enjoyed this sail. The weather was perfect, the captain wad knowledgeable about the area. We would definitely do it again!
Rating: 5
Perfect View of the Harbor
Thu, Sep 24  5:00 PM Unspecified 50-59 Domestic Tourist(s) Group of Friends
Took the sunset sail on the Adriondack III. The skipper and crew took great care of us as we sailed along the harbor. There's nothing like shutting off the engines and letting wind fill the sails. We learned historical tidbits. Relaxing, informative, a great evening out.
Rating: 5
Great experience, very friendly crew
Thu, Sep 17  6:00 PM Female 30-39 Local Couple on a Date
We had a great time- we went mid September and it was perfect weather. The crew was great, really felt like they took care of us and also shared some interesting information about the harbor islands. Abby, one of the crew members, was great, we wish her luck as she applies for med school! Thanks again! We will def be back next summer!
Rating: 5
Great anniversary date!
Sat, Sep 12  6:00 PM Female 30-39 International Tourist(s) Couple on a Date
My husband and I were visiting Boston and planned this sailing trip. We loved the experience of a real sail instead of a motorized boat. The captain and crew were very friendly and all in all it was a romantic evening with great views of the city!
Rating: 5
Want to buy me a boat
Mon, Sep 7  6:00 PM Female 20-29 Local Group of Friends
This journey inspired me to buy a boat. I probably won't, so I'll be back! Excellent service, beautiful experience.
Rating: 5
Lovely way to end the summer!
Mon, Sep 7  6:00 PM Female 20-29 Local Group of Friends
We took the Adirondack sail on Labor Day and I couldn't recommend it more highly. The sail was smooth, the view beautiful, and the crew was so personable and fun. They also had a nice assortment of drinks at a very reasonable price point. 15 minutes into the sail we decided this needs to become an annual tradition...... so we will be back!
Rating: 4
Wonderful Sunset Sail on Boston Harbor
Sun, Sep 6  6:00 PM Male 60-69 Local Family With Children
Great sail, crew members are very helpful and friendly. This is our second sail and it will not be our last. One suggestion the captain needs a microphone because if you are sitting near the front of the vessel you cannot hear his commentary.
Rating: 5
Fantastic Experience!
Sun, Sep 6  6:00 PM Female 50-59 Local Group of Friends
We were celebrating our anniversary with my daughter and friends. It was a most enjoyable event. The boat is in superior condition, the crew knowledgeable and friendly - the sunset was glorious. What more could one ask for!

we will definitely share with family and friends and repeat our sail soon.
Rating: 5
A must do!
Sun, Sep 6  6:00 PM Female 40-49 Local Couple on a Date
This sunset cruise was amazing, the staff was very nice and worked very hard. We had a great time. My husband and I are already talking about when we can do it again.
Rating: 4
Fun start to Boston vacation!
Sat, Sep 5  6:00 PM Female 20-29 Domestic Tourist(s) Family Without Children
This was a really nice way to kick off my Boston vacation with my mom over the Labor Day weekend! The crew was very accommodating and warm. They provided us with blankets for the evening breeze, and told short stories about the surrounding islands. The only negative thing I would say would be that there was really not all that much to see. The act of going sailing was nice, and coming back in we got a nice sunset view of downtown... but we didn't really go anywhere. We sort of just made a circle around a barge. Most of the navigating felt like it was done purely to entertain us (crew running around, pulling on ropes), in reality we circled one (not very exciting) area. We did get a bonus airplane landing right above the boat though, so that was neat.

Overall, it was a lot of fun, relaxing and definitely worth it, but just don't expect to explore or learn about Boston from any sort of Historical perspective!
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Displaying 1 - 10 of 113
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 an age limit for these sails?
While there is no age limit for the sails, the goal of our sailing experience is to offer a calm, serene and peaceful time for all passengers. Parents, who know their children best, should make a decision as to whether they want to bring young children. All attendees under 18 must be accompanied by a parent or guardian and everyone must have a regular-price ticket.
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.
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 sail. 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 beer, 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.
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 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 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
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