Sail Boston Harbor on Historic Schooner Denis Sullivan
Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for all fitness levels; most of the sail involves relaxed sitting, with optional light activity for sail-raising.
Overview
Set sail aboard the historic Denis Sullivan and explore Boston Harbor up close. Enjoy skyline views, fresh sea air, and support ocean education programs with this private two-hour adventure.
Details
Discover the unique experience of sailing Boston Harbor aboard the historic schooner Denis Sullivan with World Ocean School. This private two-hour Harbor Sail invites you to engage hands-on by helping raise the sails or to simply relax while taking in breathtaking views of Boston’s iconic skyline. The vessel itself is a meticulously crafted replica of a Great Lakes cargo schooner, providing an authentic, nostalgic maritime ambiance that enhances your connection to the sea. Throughout the journey, a cash bar offers refreshments, making it easy to unwind as you glide past Boston’s historic waterfront landmarks. Beyond the beauty and adventure, every ticket supports educational programs dedicated to ocean stewardship, meaning your time on board directly benefits ocean conservation and youth learning initiatives. Whether you're a seasoned sailor or a first-timer, this accessible, engaging sail lets you enjoy fresh sea breezes, stunning panoramic vistas, and a memorable taste of Boston's maritime heritage.
Adventure Tips
Arrive Early to Settle In
Plan to arrive 15 minutes before departure to get comfortable, meet the crew, and receive a safety briefing.
Dress in Layers
Boston Harbor can be breezy, so dress in layers to stay comfortable in changing weather conditions.
Bring a Camera
Don't forget your camera or smartphone to capture stunning views of the Boston skyline and harbor landmarks.
Stay Hydrated and Use Sunscreen
Even on cooler days, the sun reflects off the water, so drink water and apply sunscreen before your trip.
Local Insights
Hidden Gems
- Spectator Boat Passage near Fort Independence
- The lesser-known Rose Kennedy Greenway at the harbor edge
Wildlife
- Harbor Seals
- Great Blue Herons
History
The Denis Sullivan is modeled after 19th-century Great Lakes cargo schooners, connecting Boston’s maritime past with modern sustainable sailing education.
Conservation
World Ocean School emphasizes ocean stewardship, educating riders on marine ecosystems and minimizing environmental impact during each sail.
Frequently Asked Questions
Photography Tips
Best Times
Best Viewpoints
- Aboard the schooner deck facing Boston skyline
- Approaching Long Wharf
- Near Fort Independence with water reflections
What to Photograph
Recommended Gear
Windbreaker Jacket
Protects against wind and sea spray while sailing.
Comfortable Closed-Toe Shoes
Provides safety and stability on the deck during the sail.
Sunglasses
Shields your eyes from glare reflecting off the water.
summer specific
Water Bottle
Keeps you hydrated throughout the sail.