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Boston Sailing Trips

  • Classic Tall Ship Cruise in Boston Harbor
    Likely to Sell Out

    Classic Tall Ship Cruise in Boston Harbor

    Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Get away from the hustle and bustle of...
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     90 to 120 minutes  Free Cancellation  Instant Confirmation
    from
    $35
    Details
    from
    $35
  • Sightseeing Day Sail around Boston Harbor
    Likely to Sell Out

    Sightseeing Day Sail around Boston Harbor

    Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of...
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     90 to 120 minutes  Free Cancellation  Instant Confirmation
    from
    $66.54
    Details
    from
    $66.54
  • Sunset Sailing Cruise on a Tall Ship in Boston Harbor
    Likely to Sell Out

    Sunset Sailing Cruise on a Tall Ship in Boston Harbor

    If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $68
    Details
    from
    $68
  • Boston Harbor Sunset Sail Tour
    Likely to Sell Out

    Boston Harbor Sunset Sail Tour

    Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon....
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $82.27
    Details
    from
    $82.27
  • Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

    Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

    What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $75
    Details
    from
    $75
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Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Boston Sailing Trips?

A: According to verified reviews on City Boat Tours and TripAdvisor, the best Boston Sailing Trips are:

Q: What are the best kid-friendly options for Boston Sailing Trips Tours?

A: According to verified reviews on City Boat Tours and TripAdvisor, the best kid-friendly Boston Sailing Trips are:

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Q: Which Boston Sailing Trips have Instant Confirmation?

A: Boston Sailing Trips with Instant Confirmation include:

View all Tours with Instant Confirmation

Q: Which Boston Sailing Trips have Free Cancellation?

A: Boston Sailing Trips with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation

Q: Got any more Boston trip ideas?

A: We sure do. Check out our curated lists of hand-picked Boston Tours.

View all Boston Trip Ideas

Q: What are the most popular styles of Tours and Activities in Boston?

A: Based on our sales data over the past year, the most popular styles of tours and activities in Boston are:

View all tour styles in Boston

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City Boat Tours wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through City Boat Tours over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.