Boston Harbor Cruises - Sunset Sail

From: $120   


Rowes Wharf - Boston, MA


Mid-May through Mid-October:
Wednesday through Sunday - 6:00 PM

Click here to see schedule.

Admire the city skyline and enjoy a magnificent East Coast sunset with the Boston Harbor Sunset Sail!
  • Experienced captain and crew will entertain passengers as you are guided through the harbor on this relaxing sailing excursion
  • Leave the city noise behind and breathe in the fresh air as you sail toward the Inner Harbor Islands, Christopher Columbus Waterfront Park and other harbor highlights
  • Whether you're visiting Boston or call Beantown home, this sunset sail is the perfect way to spend a romantic evening on the water!

More detailed description >

If you're looking for a unique and perfect date night, there's no better option than the Boston Harbor Sunset Sail.

Board the impressive, 80-foot schooner for a delightful two-hour cruise. Enjoy fresh air, feel the wind in your hair and watch the sun dip beneath the horizon with the Boston skyline as the backdrop.

Your seasoned captain and crew will point out historical landmarks of the harbor, which may include (and are subject to change):

  • Inner Harbor Islands
  • The Boston Fish Pier
  • Castle Island and Donald McKay monument
  • Charleston Navy Yard
  • Christopher Columbus Waterfront Park
  • The New England Aquarium

Make yourself comfortable and enjoy an evening of sailing the beautiful Boston Harbor!

Key Info >

Essential Information:

  • Food is not included on board; snacks and picnics are recommended
  • Soda & water are complimentary. Alcohol can be purchased by anyone over 21 with a valid photo ID
  • This experience is not suitable for young children
  • Passengers must arrive 30 minutes prior to departure time; boarding is 10 minutes prior
  • Captain and crew gratuity is not included, but is appreciated

2 Hours

Maximum Participants:
This sail has a maximum of 41 passengers.

This experience is to be enjoyed by the booked participants only.

Weather Dependent:
The experience usually runs in light rain and other moderate weather situations. A trip will only be cancelled in the event of severe or unsafe weather conditions. Cancellations are made on the day of the sail, by the captain, up to one hour prior to sail time. Always contact the experience provider with any questions regarding weather conditions. In the event the sail is cancelled due to inclement weather, passengers will reschedule directly with the experience provider.

What to Wear:
Dress is typically casual. The temperature can be cooler out on the water, so dress accordingly. Please wear only soft soled shoes such as sneakers, deck shoes, flip-flops, or sandals.

Booking Information:
For this experience, it is recommended to request bookings at least 14 days in advance.

Cancellation Policy:
Prior to scheduling/booking a date for this experience, Cloud 9 Living's standard return and exchange policy shall apply. Once you have scheduled a date and received a booking confirmation, no refunds will be given. Rescheduling is not allowed and all bookings are final. Failure to appear on your booked date will result in the loss of the value of your experience.

Experience ID:

View FAQ's >

  1. Is food served on board?
    Food is not served on the sailing experience. Complimentary soda and water will be served and alcoholic beverages are available for purchase. You may bring your owns snacks.
  2. Are there any age restrictions?
    This experience is not recommended for young children.
  3. Is the schooner handicap accessible?
    No, unfortunately the schooners are not wheelchair accessible.
  4. Will I get seasick?
    The Adirondack III is a gentle, steady vessel. Most people do not experience seasickness.
  5. Is there a bathroom on board?
    Yes, the boat is equipped with a bathroom that is accessible at all times.
  6. Is there parking close to the ship?
    Limited metered parking can be found around Rowes Wharf. There is also paid parking available at the Boston Harbor Hotel.

Customer Reviews:

  • Boston Harbor Sunset Sail

  • September 29, 2015

  • 4-half

  • Boston

"The sail cruise was very nice and all employees were very professional. I will definitely do this again and use Cloud 9 Living in the future. "

  • Boston Harbor Sunset Sail

  • September 09, 2015

  • 3-half

  • Boston

"This was a gift from our children, so I do not know how much it cost, but not sure it was worth it. They take you out from the dock, sail around a little bit and tell you about a few of the islands and bring you back. The staff was friendly, but had little interaction with the guests. The boat was nice, but not overly comfortable. "

  • Boston Harbor Sunset Sail

  • September 02, 2015

  • 4-half

  • Boston

"We had a wonderful night for a sunset sailboat cruise. The intimacy on the boat was perfect, just 40 people. The 2 deckhands (Abbey and, I wish I could remember his name) were fun to watch, personable, attentive and knowledgeable. It was captain Pete's birthday and he was a little surprised when I called it out for all to hear. His coworkers at the ferry terminal posted it on the message board. The sunset was terrific, the skyline lit up beautifully, perfect for a leisurely cruise. Awesome to see Royal Caribbean's 'Liberty of the Seas' pass us on the way out of the harbor. The only recommendation I would suggest is a lapel microphone with a small amplifier so the captain or deck hands could speak a little more about the harbor islands and some history. I'm from Boston so I know, but for vacationers I think that would be a nice touch. they seem to advertise it as a narrated cruise but it appears you have ask to get them speaking (unless the captain did and we couldn't hear because we at the front of the sailboat). We thoroughly enjoyed our night and we look forward to using Cloud 9 again soon."