August Adventures Sailing on Denis Sullivan in Boston Harbor
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels; participants should be able to move safely around the deck.
Overview
Join the World Ocean School for a memorable family sail aboard the Denis Sullivan in Boston Harbor. Experience hands-on sailing, beautiful skyline views, and quality time on a historic schooner.
August Adventures aboard Denis Sullivan
All Ages • Free! Sponsored by Highland Street Foundation
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About This Adventure
Experience the thrill of sailing aboard the Denis Sullivan, a stunning Great Lakes replica schooner, during our Family Sails in Boston Harbor. Join the crew in raising the sails or simply soak in the breathtaking skyline. This unique adventure is perfect for local families seeking memorable moments together. Reserve your spot today!
Reserve your spot today!
Duration
2 Hours
Boarding will begin 15 minutes prior to start of sail.
6/23/25 Update: August Adventures aboard Denis Sullivan is currently SOLD OUT. We are offering standby boarding first come, first serve to those who were unable to reserve tickets. Please come to the Moakley Courthouse Docks 10-15 minutes prior to either sail. Spots are not guaranteed.
If you are running late, please call 617-816-9247 at least 15 minutes prior to the start of your sail, otherwise, your spot may be given away. If you are unable to make the sail, please give us a call, so we can open up the spot.
About
We are thrilled to offer Family Sails as part of August Adventures 2025, sponsored by Highland Street Foundation. Join World Ocean School for a two-hour sail aboard our schooner Denis Sullivan!
Come aboard this Great Lakes replica schooner to enjoy a cruise around Boston Harbor with family and friends. You can join our crew in raising the sails of our tall ship—or just relax and enjoy the beautiful Boston skyline with your family. These special sails are intended for local families to experience this authentic adventure in Boston Harbor. As space is limited for the sails, please only reserve space if you intend to participate, and let us know in advance if your plans change so we can accommodate others.
The schedule for each event is as follows: 10am-12pm Family Sail
1pm-3pm Family Sail
Please note, we will be offering standby boarding first come, first serve, beginning 10 minutes prior to the sail departure time. Guests who are unable to reserve a spot for the sail are encouraged to gather at the top of the gangway for standby participation.
Given that we will be accepting standby passengers, if you are running late to the check-in (15 minutes prior to sail time), please call (617) 816-9247 to confirm your participation, otherwise your spot may be given to another passenger.
More Info: A cash bar with a range of nonalcoholic beverages are available for purchase aboard the vessel during the sail.
Adventure Tips
Wear Comfortable Non-Slip Shoes
Deck surfaces can be slippery, so sturdy non-marking footwear helps keep you safe while moving around.
Bring Sunscreen and a Hat
Protect yourself from sun exposure during the sail, especially on clear summer days.
Dress in Layers
Even in summer, coastal breezes can be cool; layering allows you to adjust comfort levels throughout the sail.
Arrive Early for Check-In
Plan to arrive 15 minutes before departure to complete check-in and get briefed on safety procedures.
Local Insights
Wildlife
- Ospreys
- Harbor seals
History
The Denis Sullivan is modeled after 19th-century Great Lakes schooners, vessels crucial to regional trade and transportation.
Conservation
World Ocean School promotes sustainable sailing practices focused on protecting Boston Harbor's marine ecosystem.
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Adventure Hotspots in Boston
Frequently Asked Questions
Recommended Gear
Non-slip Sailing Shoes
Ensures safety and stability on the wet deck.
Layered Clothing
Adjusts easily to changing weather and cool ocean breezes.
spring specific
Sunscreen
Protects skin from sun exposure during open water sailing.
summer specific
Water Bottle
Keeps you hydrated throughout the sail.