City Lights Sail

Classic Harbor Line

Zerve Seller: BostonSail
Activity #4094
  • Everyone says Boston is best seen from the water! See all of our city's greatest attractions on our one-of-a-kind sightseeing sail.

  • Spend a wonderful evening watching the lights dim over Boston as we set sail & witness a beautiful sunset across the city's horizon.

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


This serene sail allows you to experience Boston with peaceful tranquility. Enjoy the evening sea breeze swirling around you and all of Boston as your backdrop. Take-in the shimmering city of Boston on a smooth, gentle sailing vessel with some speediness to boot.

Adirondack III, an elegant 80 foot pilot schooner, will act as your chariot through the Boston Harbor waters. The Adirondack III offers a comfortable ride that is brisk and invigorating.

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

Enjoy the historic scenery of Boston Harbor:
  • Check out the evening lighting of the Bunker Hill Monument and Old Ironsides, also known as the USS Constitution in the Charleston Navy Yard
  • Enjoy the lighting on the iconic buildings and bridges of Boston Harbor such as: International Place, the arch at the Boston Harbor Hotel, the Marriott Custom House Tower, New England Aquarium, The Lenorad Zakim Bridge, and The Mystic Tobin Bridge
  • Enjoy the bustling evening along the North End waterfront.
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.
  • 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.)
23 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 1 3 0 = 3 100% 5.0
Last 6 months 1 3 0 = 3 100% 5.0
Last 12 months 14 34 0 = 34 100% 4.7
All 23 55 0 = 55 100% 4.7
23 Reviews
Displaying 1 - 10
Sort by: Date Attended Gender Age Where From Group Type
Rating: 5
Great ride, beautiful sights
Sat, May 21  9:00 PM Male 20-29 Domestic Tourist(s) Couple on a Date
Well done, don't change anything.
Rating: 4
Great night! Great trip!
Fri, Sep 4, 15  8:30 PM Unspecified 50-59 Local Couple on a Date
Nice night. Not a lot of wind, but the crew recognized that it was a low key crowd and went with the mood. Great drink service, relaxing cruise!
Rating: 5
Beautiful quiet night in Boston Harbor!
Sat, Aug 29, 15  8:30 PM Female 50-59 Domestic Tourist(s) Group of Friends
It was a pleasant night and there was a fabulous full moon. The schooner is not large but there was plenty of room for us to sit and when the sails were up and Capt Pete cut the engines it was wonderfully peaceful. The young mates are pleasant and helpful, there was a nice selection of beer and wine for $5 with free soda and water. We brought sandwiches for supper and it was heavenly. No commentary, no music, just a peaceful sail with quiet conversation The only thing I hadn't realized in advance is that it would be a little challenging for seven of us to converse with each other since we were all side by side. But we'd all be back - maybe for the sunset sail next time.
Rating: 5
Great Experience !!!!!!
Sat, Aug 15, 15  9:00 PM Male 50-59 Local Family With Children
Great time and crew was great. City lights were spectacular and lightening in the distance gave us an unforgettable night. The crew was constantly vigilant regarding the weather and never did we worry about our safety. A must do for locals and tourist alike !
Rating: 5
Tasteful and classy sailing excursion!
Fri, Aug 14, 15  9:00 PM Male 20-29 Local Couple on a Date
I was looking to take my girlfriend for a nice, quiet cruise on Boston harbor, and I was disappointed that all the options seemed to devolve into loud EDM dance parties. Thankfully we found this cruise and enjoyed a classy, romantic sail on the Adirondack III. The crew was friendly, personable, and took care of everything for us. I would definitely pay to do this again.
Rating: 5
Wonderful Trip
Fri, Aug 7, 15  9:00 PM Female 40-49 Domestic Tourist(s) Couple on a Date
We had such a lovely time on this night sale. The view was amazing and relaxing. The crew was very kind and hospitable and enjoyable to chat with. This wasn't a party cruise which was so much better to enjoy a nice quiet evening with a couple glasses of wine. I would definitely recommend this trip.
Rating: 5
Great Evening
Sat, Jul 25, 15  9:00 PM Male 40-49 Domestic Tourist(s) Family Without Children
My wife and I went on the City Lights cruise and it was perfect. The three member crew allowed us to simply sit and enjoy the sites. If we had a question, they answered it, but they just allowed everyone to take in the sites and relax. Blankets were available as it was a little chilly. One of the best things we did on our short holiday to Boston.
Rating: 4
Fri, Jul 24, 15  9:00 PM Male 30-39 Domestic Tourist(s) Unspecified
Peaceful and enjoyable
Rating: 4
Great tour, great views for the evening tour
Fri, Jul 24, 15  9:00 PM Unspecified Unspecified Unspecified Unspecified
Like I said, great tour of the city skyline at night with great views. However other guests were disruptive by means of overly loud young girl gaggle and "selfie" camera flashes.

Could have been a very romantic evening, just other guests were disruptive.
Rating: 4
Great Sailing experience
Sat, Jul 18, 15  9:00 PM Male 50-59 Domestic Tourist(s) Family With Children
Could have used a narration describing sites of the Harbor. However the sailing experience was fabulous. Quiet just the sound of the win and water hitting the ship....
Displaying 1 - 10 of 23
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.
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.
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 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 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.

Weather Policy

Activity may be cancelled 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) or receive credit for a future 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.
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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