BOSTON sailing Tours

Private Sailing Charters for up to 6 guests around Boston Harbor & Islands.

Boston Sail Tours

Sailing Charters Boston Harbor

Sailing Charters for up to 6 guests around Boston Harbor & Islands

Explore Boston Harbor and

the harbor Islands

with Boston Sail Tours


Welcome to Boston Sail Tours, your premier private sailboat charter. Whether you're planning a special occasion or seeking an escape into nature, our tours are designed for you.


Why Choose Us?


1. A variety of unique tours


An island destination. A nature lover's dream, only accessible by private boat. Yours for a full day!

We are the unique sailing tour that offers an exploration tour of the pristine Lowells, Grape and Bumpkin Islands only accessible by private boat. You will be able to disembark and discover secluded beaches, nature and wildlife including deer. This extraordinary experience is only a 1.5-hour sail from downtown. 


A half day sailing experience around the Islands. A tour in the past.

Let us take you back in time. We will pass the unchanged stone fortress and rugged coastline of the islands. Experience the pristine islands aboard a traditional sailing vessel as if you were seeing them 200 hundred years ago. You are welcome to take the helm!


Two-hour private harbor sail: Available Morning, afternoon, and sunset.

Bring your favorite food and beverages or take advantage of our complimentary refreshments., 

Celebrate birthdays, anniversaries, engagements or simply enjoy your special moment and the breathtaking view of the city skyline. Daytime and sunset sails are available.           


2. Easy booking and fair prices 


  • Ease of Booking: Secure your spot with ease— reservations can be made up to one hour before departure.
  • Minimal booking deposit
  • Comprehensive cancellation policy 
  • Best prices: We strive to offer the best prices to ensure that our tours are accessible to everyone. 


3. Bathroom and comfort Onboard

Enjoy a ride on a sailboat impeccably maintained and specially designed for comfort at sea with a spacious cockpit and full-size bathroom.


4. Our boat is part of local naval history

Our boat Francesca is a cutter Ketch (2 masts and 4 sails) with a clipper bow, a traditional design by John G. Alden Design Co. (1909 -2008) of Boston. The firm is part of local history and was the Longest operating naval architecture company in the US. The boat design can be viewed at MIT museum in Cambridge. 


5. The longest Sailing season

Our sailing season runs from Marathon Day on April 15 through the Beautiful New England leaf season on the fall. This period offers the most pleasant weather and ideal sailing conditions allowing you to enjoy the natural beauty and serenity of the area fully.


6. A flexible daily schedule

  • We sail every day from 10 Am to 10 Pm
  • Departure every hour on the hour.


Ready for an unforgettable journey? Book your private sailing charter through our website or contact us at 617-279-3981 and experience the unique charm of Boston Harbor and its islands with us.

Explore Boston Harbor and the harbor Islands

with Boston Sail Tours


Welcome to Boston Sail Tours, your premier private sailboat charter. Whether you're planning a special occasion or seeking an escape into nature, our tours are designed for you.


Why Choose Us?


1. A variety of unique tours


An island destination. A nature lover's dream, only accessible by private boat. Yours for a full day!

We are the unique sailing tour that offers an exploration tour of the pristine Lovell's, Grape and Bumpkin Islands only accessible by private boat. You will be able to disembark and discover secluded beaches, nature and wildlife including deer. This extraordinary experience is only a 1.5-hour sail from downtown. 


A half day sailing experience around the Islands. A tour in the past.

Let us take you back in time. We will pass the unchanged stone fortress and rugged coastline of the islands. Experience the pristine islands aboard a traditional sailing vessel as if you were seeing them 200 hundred years ago. You are welcome to take the helm!


Two-hour private harbor sail: Available Morning, afternoon, and sunset.

Bring your favorite food and beverages or take advantage of our complimentary refreshments., 

Celebrate birthdays, anniversaries, engagements or simply enjoy your special moment and the breathtaking view of the city skyline. Daytime and sunset sails are available.           


2. Easy booking and fair prices 


  • Ease of Booking: Secure your spot with ease— reservations can be made up to one hour before departure.
  • Minimal booking deposit
  • Comprehensive cancellation policy 
  • Best prices: We strive to offer the best prices to ensure that our tours are accessible to everyone. 


3. Bathroom and comfort Onboard

Enjoy a ride on a sailboat impeccably maintained and specially designed for comfort at sea with a spacious cockpit and full-size bathroom.


4. Our boat is part of local naval history

Our boat Francesca is a cutter Ketch (2 masts and 4 sails) with a clipper bow, a traditional design by John G. Alden Design Co. (1909 -2008) of Boston. The firm is part of local history and was the Longest operating naval architecture company in the US. The boat design can be viewed at MIT museum in Cambridge. 


5. The longest Sailing season

Our sailing season runs from Marathon Day on April 15 through the Beautiful New England leaf season on the fall. This period offers the most pleasant weather and ideal sailing conditions allowing you to enjoy the natural beauty and serenity of the area fully.


6. A flexible daily schedule

  • We sail every day from 10 Am to 10 Pm
  • Departure every hour on the hour.


Ready for an unforgettable journey? Book your private sailing charter through our website or contact us at 617-279-3981 and experience the unique charm of Boston Harbor and its islands with us.

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