Water Activities & Boston Sailing Tours: Harbor Adventure
Difficulty
easy
Duration
2 hours
Fitness Level
All fitness levels welcome; moderate comfort on a boat is helpful
Overview
Set sail on Boston Harbor with Boston Sailing Tours—an unforgettable two-hour cruise that combines city views with nautical fun. Perfect for celebrations or a relaxing escape, this adventure offers stunning scenery and a personalized experience on the water.
2-Hour Day/Sunset/Night Sail
For all ages! • 2 Hours • Up to 6 People
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About This Adventure
Experience the beauty of Boston Harbor on a relaxing two-hour sail, perfect for special occasions like birthdays or proposals. Enjoy stunning views of iconic landmarks such as the USS Constitution and Castle Island while bringing your favorite food and music aboard. Create unforgettable memories on this unique sailing adventure.
Day/Sunset Sail Monday - Friday $545
Weekends, and Holidays $595
Night Sail Fridays & Saturdays 8:30 pm - 10:30 pm $795
20% is due at the time of booking. The remaining balance is due at the time of the charter.
Departing Location
Boston Sailing Tours departure location is at Courthouse Docks, Located Across From Marcelino's Seaport - 2 Northern Ave, Boston, MA 02210. All trips will depart from this location. Paid public parking is available. MAP
Duration
2 Hours
About
Spectacular views of the Boston Harbor skyline, a very relaxing sailing experience for your special event. The perfect stage for a unique moment… Birthdays, proposals, memorials, or simply cruising along.
This is a complete tour of the inner harbor. You will sail by the USS Constitution, the North End, the Seaport District, Castle Island, and East Boston.
What to Bring
CONSIDER TO BRING Sailors should dress for safety, comfort, and weather. In spring and fall, dress in layers and bring a jacket or sweatshirt; it can be cooler at sea than on land.
In summer, bring a hat, sunglasses, and sunscreen.
For safety and comfort, soft-soled shoes like boat shoes or sneakers are the preferred footwear aboard the Francesca. You will be asked to go barefoot for safety reasons if you wear hard-soled shoes or high heels on board.
What Not To Bring
'Per Federal regulation no marijuana or marijuana-containing products no illicit drugs
Food, Drinks, Music
• You’re welcome to bring your favorite food, drinks, and music. • We recommend easy-to-eat items and canned drinks. • We do not have a formal table in the cockpit • We have complimentary water and sodas on board
FULL GUEST INFORMATION
Adventure Tips
Arrive early for the best seats
Getting to the boat early ensures you secure a prime spot with the best view and space to relax.
Bring layers for comfort
Bring weather-appropriate clothing, as it can get breezy on the water during the sail.
Photos at sunset are stunning
Plan the sail during sunset hours for the most dramatic skyline photos.
Sample local seafood afterwards
Combine your sail with a visit to waterfront restaurants for a full maritime experience.
Local Insights
Wildlife
- Seagulls
- Harbor seals
History
Boston Harbor has been a vital maritime hub since colonial times, shaping the city’s economy and culture.
Conservation
The harbor is actively managed to preserve water quality and protect local wildlife.
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Adventure Hotspots in Boston
Frequently Asked Questions
Recommended Gear
Sunscreen
Protect your skin during the daytime sail.
summer specific
Windbreaker or light jacket
Stay comfortable on breezy evenings or in case of light rain.
spring; summer; fall specific
Camera or smartphone
Capture the city skyline and harbor vistas from the water.
Hat and sunglasses
Shield yourself from sun exposure while enjoying the cruise.
summer specific