• Eastern Point Lighthouse, marking the entrance to Gloucester Harbor
• Ten Pound Island Lighthouse, located on a small island within the harbor
• Gloucester’s historic beaches and rugged coastline
• Historic waterfront homes and estates, including the renowned Sleeper-McCann House
• The working Gloucester waterfront and surrounding harbor
• Numerous schooners sailing throughout the harbor as part of the Gloucester Schooner Festival

• No food is included. Feel free to bring your own picnic!
• The price of drinks is not included in the cost of your ticket – please bring a credit card to purchase on board.
• Credit Cards are the only form of payment accepted on your cruise. Please plan accordingly.
• Please bring valid identification with you. Identification is checked prior to boarding for guests interested in an adult beverage.
• Gratuity is not included in the price of your sail.
• Beverages and Coolers: Outside adult beverages and coolers are not allowed aboard.
• We reserve the right to add a 15% gratuity for parties of 12 people or more, regardless of whether they are booked together or not.

• 63 Rogers Street, Gloucester, MA 01930

Call us directly at (617) 951-2460.

• Serene Sunset Sail

  Travelling on a sailing boat gives a sense of serenity while also being close to the elements. The views around the harbour and back to the city are beautiful. The crew and particularly our captain, Alison, were professional, knowledgeable and very friendly. Sipping a glass of wine while watching the changing colours across the harbour as the sun went down is a truly fabulous way to end a great day of sightseeing in Boston.

  – Paulwelch0

• Perfect Experience

  The two hours we spent on the sailboat were the most relaxing two hours I have had in some time. It was absolutely beautiful, the staff was helpful and kind and the next time I am in Boston I will be going on another sail. Highly recommend this experience to anyone visiting Boston, or even locals looking for a relaxing activity away from the craziness of the city.

  – mroyal87

• Everything we hoped for!

  What a beautiful night it was for a sail. Plenty of wind to allow the great crew to do their thing. Pushing 10 knots on smooth water is a quiet, thrilling yet relaxing time. The sunset was fantastic, wish we could post a picture here.

  – SCALEF

• Great Night

  It was one of the most fun filled nights on the water I’ve had in a long time. Sailing around Boston Harbor, going by the Islands what more could you want for a summer. Boston has the most beautiful skyline. I will be back before the summer is over.

  – harrow

• Wonderful Date Night

  This was a great way to spend an evening getting to see a different side of Boston. The crew was super friendly; pointing out landmarks and making sure we got a great sunset photo. They even provided blankets to help ward off the chill. It was a great date night and wonderful way to spend our last night in Boston.

  – Shellev

• Wonderfully relaxing evening

  I took my husband on this sail as a birthday surprise. We had a fabulous time. It was so relaxing and the wind was perfect for a great sailing experience. The Captains and staff were super friendly, knowledgable and were a very positive addition to the experience. I would do this again in a heartbeat.

  – Kpoll325

An option to reschedule or convert to a gift certificate is available up until 24 hours prior to departure. We are not able to offer refunds. Requests for cancellation, rescheduling or conversion to gift credit must be sent by email to [email protected]. Most activities run regardless of weather conditions. In the rare situation where the seller is forced to cancel the event, ticket-holders will be allowed to reschedule to another time (subject to availability), receive credit for a future event, or receive a refund.

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 credit for a future event, or receive a refund.

All participants are required to have tickets for this event. According to the U.S. Coast Guard capacity rules, all passengers including infants and toddlers must have a ticket.

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.