Boston Harbor Sunset Sails

Boston Harbor Sails aboard Roseway

Various Dates May through September

What better way to enjoy the summer in Boston than with a sail aboard Roseway? Join us for a spirited two- hour harbor sail aboard Boston’s only historic tall ship. Help us raise the sails, meet and talk with the crew, take the helm, explore below decks, or just sit back and enjoy the summer breezes and Boston’s beautiful cityscape. Walk across the gangway and gain a perspective of the city like no other - Roseway allows you to enjoy nature and celebrate the city!

These sails serve two purposes: they are an opportunity for World Ocean School to open Roseway to the public, sharing her unique role as an active National Historic Landmark, and they serve as a source of revenue for the World Ocean School’s ongoing educational programs. All proceeds support our programs.

Reservations are required.  Pick-up and drop-off at the Moakley Federal Courthouse Dock (2 Northern Ave.) in downtown Boston. Boarding begins 15 minutes prior to departure. Roseway sails rain or shine unless conditions are unsafe. In such cases we will contact you prior to the sail for re-scheduling.

Dates: See the drop-down menu on the right hand side of the page for available dates and times. We frequently add new sail dates, so check back often!    
Tickets: Purchase tickets using the checkout system in the sidebar. If you are unable to purchase them online call the office phone number during office hours.
Adults: $55 | Seniors (65 and above): $45 | Children (12 and under): $45

A couple of things to know before you purchase tickets:

  1. Beer, wine, soda, water and snacks are available for purchase on board. In order to consume alcoholic beverages on this sail, you must be 21 years of age. A photo I.D. will be required upon boarding. Due to our liquor license passengers are not allowed to bring their own alcohol aboard the vessel. 
  2. Tickets are non-refundable. If you find you are unable to use them, you can apply your tickets to another event or date; you can gift them to someone else to use; or you can turn them into a tax-deductible donation to the World Ocean School.

How to find us: Boston is a walking city with very limited parking, so we recommend you do not drive to the dock location. The Courthouse Dock is located less than a block from the Silver Line MBTA station, next to the old Daily Catch Restaurant at 2 Northern Avenue. 

The closest MBTA stops are:

  • Courthouse - Silver Line - about a 3 minute walk
  • South Station - Red Line, Silver Line, Commuter Rail - about an 11 minute walk
  • Aquarium - Blue Line - about a 13 minute walk
  • Downtown Crossing - Orange Line, Red Line - about a 16 minute walk

Questions? Contact us (617) 816-9247 or

The office is open Monday - Friday 9am-5pm; if you have questions about the logistics of your sail outside of those hours please call the boat phone 617-755-7241.