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.)
66 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 12 30 0 = 30 100% 4.8
Last 6 months 12 30 0 = 30 100% 4.8
Last 12 months 50 123 0 = 123 100% 4.7
All 66 167 0 = 167 100% 4.8
66 Reviews
Displaying 1 - 10
Sort by: Date Attended Gender Age Where From Group Type
Rating: 4
Great crew!
Sat, Jun 27  6:30 PM Male 30-39 Local Couple on a Date
Weather wasn't perfect, but trip was still fun and worth it.
Rating: 5
Great sail!
Sun, Jun 21  6:30 PM Female 30-39 Local Family Without Children
We had a great time on the Adirondack! The crew was knowledgable and friendly and the cruise around Boston harbor was beautiful.
Rating: 5
Would go again!
Sun, Jun 14  6:30 PM Female 20-29 International Tourist(s) Family Without Children
I had a wonderful time and experience. Would definitely recommend to others and go again.
Rating: 5
Beyond expectations!
Fri, Jun 12  6:30 PM Female 20-29 Domestic Tourist(s) Couple on a Date
I was looking for a memorable birthday for my boyfriend. We happened to be in Boston for the weekend so we looked forward to make the best of it. He was not aware of my plans of going sailing so to him this all was a surprise. The experience was beautiful. The sail was smooth and you were able to capture key historical places in Boston. I loved my time there and staff was amazing. We picnicked and drank some prosecco. No food is offered so I made it my job to bring cheese, crackers, grapes and other finger foods. I recommend it --being that its a 2hr ride and during dinner time. it got a little cold but staff was prepared with blankets to keep you warm. The time of the day-- it being sunset gave room to enjoy the bright sun til it sets and great pictures can be taken. totally recommend it!
Rating: 4
Great crew, great boat
Thu, Jun 4  6:30 PM Female 60-69 Domestic Tourist(s) Family With Children
The crew was just great and the boat very well kept! Our only issue was the weather - it was cold and windy, however, we were provided with as many blankets as we wanted to keep warm. On a warmer evening it would be a lovely spot to relax after a busy day of touring.
Rating: 5
Relaxing cruise and amazing pictures
Fri, May 29  6:30 PM Male 40-49 Domestic Tourist(s) Couple on a Date
This was one of the best parts of our trip to Boston and the sunset pictures are amazing.
Rating: 5
Great time
Fri, May 29  6:30 PM Male 50-59 Local Couple on a Date
Surprised my wife for her birthday and we had a great time

The crew was the best and the whole experience was so fun and easy
Rating: 5
Sunset Cruise
Sun, May 24  6:30 PM Female 30-39 Local Couple on a Date
Incredible sunset sail. Wonderful and dedicated captain and crew! Really enjoyed the beautiful sights in the Boston Harbor as the sun was setting. Especially enjoyed watching the cannon at sunset in the Navy Yard!
Rating: 5
What a rush
Fri, May 22  6:30 PM Male 50-59 Domestic Tourist(s) Family Without Children
Leaning back with all the mad, swirling wind of the harbor thrust in my face I laugh to feel the rush as the boat heels over and slams into the water with white, foaming sea lapping at the gunnels. The flap of sail going suddenly taught with a CRACK! that startles my work numbed senses, and we really begin to move, to climb onto the water and shoot toward the horizon. It has been forever since a tour jolted me so firmly and made all the brilliant color and depth of Boston alive and new again. Get in, sit down, take the ride and feel new again, awake and full of life.

No kidding.

Rating: 5
Great relaxing way to see Boston
Fri, May 15  6:30 PM Female 60-69 Domestic Tourist(s) Family Without Children
Enjoyed the captain's commentaries-knowledgable, personable. Informal. Boat had comfortable seating. Blankets to curl up in if it got cool. Attentive staff. We were able to bring our own picnic; drinks were cold and reasonable. Had a unique leisurely view of the harbor and watched the skyline light up as we returned to the harbor. Would definitely do it again.
Displaying 1 - 10 of 66
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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