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Boston Harbor Sailing Cruise

Sail Boston Harbor on a classic schooner, enjoying iconic views and a relaxing atmosphere. Perfect for families and friends seeking a unique perspective of the city.

Boston
1 hr 30 min
3.38Rating:
2 providers combinedLast updated: March 29, 2026

Provider Score Distribution

Cumulative distribution showing how many tours score at or below each rating on each provider platform in Boston.

Provider Scores

Viator logo
4.77
542 reviews
GYG logo
4.76
227 reviews

Important Information

  • Children must be accompanied by an adult
  • Minimum drinking age is 21 years
  • Dress for cooler weather on the water
  • Service animals allowed, no pets
  • Arrive 15-30 minutes before departure
  • Boarding begins 5 minutes prior to departure

Experience the charm of Boston Harbor on a classic sailing cruise. Choose between a 1.5 or 2-hour journey aboard the elegant Adirondack schooners. As you sail past landmarks like Castle Island and the Inner Harbor Islands, feel the wind in your hair and the thrill of the open sea. The knowledgeable crew is ready to answer your questions about the sights and history of Boston Harbor. Enjoy the option to purchase beverages onboard, and bring your own picnic to savor while you relax. This Boston Harbor Sailing Cruise is perfect for families and friends looking to enjoy the city's stunning waterfront from a unique perspective. Book your adventure today and create unforgettable memories on the water.

Pros

  • Sail past Boston's iconic landmarks
  • Feel the wind in your hair on a classic schooner
  • Admire the Inner Harbor Islands
  • Enjoy beverages available for purchase
  • Relax as the crew answers your questions
  • Capture stunning views of Boston's skyline

Includes

  • 1.5 or 2-hour sailing experience
  • Captain and crew
  • Soda and water

Excludes

  • Food
  • Gratuities
  • Beverages available for purchase by credit card
  • Personal expenses

FAQ

  • What Should I Bring?

    Bring a photo ID, a water bottle, and dress for cooler weather.

  • Are Pets Allowed?

    Only service animals are permitted; no pets or emotional support animals.

  • Can I Bring My Own Food?

    Yes, you are welcome to bring your own picnic aboard.

  • Is There a Restroom on Board?

    Yes, restrooms are available on the schooner.

  • How Do I Pay for Drinks?

    Beverages can be purchased onboard with a credit card.

$66.54
3.38Rating:

Tour Highlights

  • Sail past Boston's iconic landmarks
  • Feel the wind in your hair on a classic schooner
  • Admire the Inner Harbor Islands
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