Where to Go Sailing in Boston

Best Boston sailing schools, lessons, clubs, charters

Sailing in Boston Harbor at dusk
Sailing in Boston Harbor at dusk

If you love sailing, Boston offers plenty of opportunities.

You can learn to sail, advance your sailing skills, arrange boat charters, and enjoy other water sports such as kayaking and windsurfing - even if you're here for just a short visit. 

Boston's waterfront location puts sailing, kayaking, and boat charters right on your doorstep. 

And if you visit the city frequently, you might even consider a membership in a Boston sailing club where you'll get boat access or fractional sailboat ownership.

Here are five Boston sailing school options, boat charters, and clubs for you to consider.  

Have fun sailing and kayaking in Boston!


Boston Sailing Center

Sailing in Boston at Boston Sailing CenterHeadquartered in a Louisiana riverboat docked at Lewis Wharf on Boston Harbor in the North End, Boston Sailing Center offers a wide range of sailing lessons as well as club memberships. 

Although Boston Sailing Center's regular season runs between May 1 and November 1, special "frostbite" racing, seminars, navigation classes, social activities, and even charters to warmer waters extend the fun through the winter months.

Founded in 1977, this popular Boston sailing club offers unrestricted sailing along the historic waterfront and around the Harbor Islands.  You can also take overnight trips to Marblehead and longer trips to places like Provincetown on Cape Cod, Nantucket, Martha's Vineyard, and Newport. 

A number of sailing club membership options are available, depending on the type of vessel you want.  You also get boat privileges for a period of time after taking classes.

Serious sailors love the Boston Sailing Center memberships.  In addition to basic sailing skills, classes include specialized skills, navigation, and racing.  Individual lessons are also available.  And for the ultimate experience, join one of the winter Caribbean cruises and learn to sail in tropical waters.

Boston Sailing Center's memberships and instructional programs are understandably geared toward residents, who of course will be here for more than just a few days.  But if you're visiting for only a short time, you'll still find some attractive options here.

If you're visiting Boston, choose a 1-week class, or take a private lesson for just an afternoon to jump-start your skills and fit with your schedule.

You can also charter a boat for a reasonable hourly fee, which is based on the size and type of boat.  A 2-hour minimum applies for Boston boat charters.

Finally, for not much more than you'd pay for chartering a boat for 3-4 hours, you can opt for a "mini" 30 day membership.  The fee for this also depends on the size and type of boat.  Even if you use the boat just for a day, you may come out ahead.  And if you're going to be here for 30 days - well, that's even better!

Essentials:  Boston Sailing Center

Location:  Lewis Wharf, North End, Boston
More information:  617-227-4198; website 
Nearest T station:  Blue Line/Aquarium
Hotels near Boston Sailing Center:

  • Fairmont Battery Wharf Hotel - North End luxury hotel near Lewis Wharf - Rates/reviews
  • Millennium Bostonian - 7-8 minute walk through the North End to Lewis Wharf; near Faneuil Marketplace - Rates/reviews
  • Marriott Long Wharf - Located on the edge of the North End, next to the New England Aquarium - Rates/reviews


Boston Harbor Sailing Club

The Boston Harbor Sailing Club located on Rowes Wharf near the Boston Harbor Hotel offers lessons plus the possibility of boat rentals and charters.  Rentals are available only when its 60+ vessels aren't being used by club members.  To rent a boat, you need to have certifications or experience appropriate for the size vessel that you want to take out.  You can also charter a boat.

Boston Harbor Sailing Club offers weekend and week-long lessons - so if you want to learn how to sail, check out their schedule and plan your Boston visit accordingly.   And if you want the advantages of fractional sailboat ownership, check out their club options.

Club memberships, rentals, and lessons are all reasonably priced.

Essentials:  Boston Harbor Sailing Club

Location:  Rowes Wharf, Downtown Boston Waterfront
More information:  617-720-0049; www.bostonharborsailing.com 
Nearest T station:  Blue Line/Aquarium, Red Line/South Station
Hotels near Boston Harbor Sailing Club:

  • Boston Harbor Hotel - Luxury hotel next to Rowes Wharf- Rates/reviews
  • Hilton Boston Financial District - 5-minute walk to Rowes Wharf - look for attractive weekend rates - Rates/reviews


Black Rock Sailing School

The Black Rock Sailing School, located on Fan Pier in the South Boston Waterfront, offers both year-round lessons (including advanced class in the Caribbean during winter months), charter trips, and a couple of different club options to give you access to sailboats and yachts with the advantage of fractional sailboat ownership at a reasonable price.

Classes are small - typically a maximum of 3 people plus the instructor, although an exception will be made if two couples want to do a class together.  Private lessons are also available.  You can earn ASA (American Sailing Association) certification here.

Black Rock offers a variety of class formats, including 3-day "long weekend" classes designed especially for Boston visitors who make the classes the focus of their vacation here.  Black Rock will also customize to fit your needs.

Essentials:  Black Rock Sailing School

Location:  Fan Pier, South Boston Waterfront
More information:  617-639-3016; www.blackrocksailingschool.com 
Nearest T station:  Silver Line/Seaport (connect at Red Line/South Station)
Hotels near Black Rock Sailing School:

  • Renaissance Hotel - About 2 blocks from Fan Pier - Rates/reviews
  • Intercontinental Boston - About a 5-minute walk across the Moakley Footbridge to Fan Pier - Rates/reviews
  • Langham Hotel - 7-8 minute walk to Fan Pier - enjoy their spa after sailing - Rates/reviews

Community Boating - Sailing on the Charles River

Community Boating, located on the Charles River Esplanade near the Charles Street pedestrian bridge, is one of the most popular programs in Boston for sailing, kayaking, and windsurfing lessons for kids and adults. 

Sailing in Boston at Community Boating
Sailing in Boston Harbor at Dusk

Begun in 1936, the non-profit Community Boating is also the largest, oldest, and one of the best public sailing program in the United States.

The Junior Program offers sailing, kayaking, and windsurfing classes from mid-June through mid-August for kids between 10 and 18, plus unlimited use of the boats.  To participate, kids must be able to swim 75 yards.

All instructors are US Sailing Level One certified, and many of them learned to sail here themselves. 

Kids pay a membership fee, and can take as many classes as they want.  They also get unlimited use of the boats, windsurfers, and kayaks from 9am until 3pm Monday through Friday. 

Beginning classes last a week, and more advanced classes are even shorter. 

Community Boating Boston is easily reached by the subway or by walking, and while your children are out on the water, you can explore nearby Beacon Hill and other parts of the city.

Or you can also join them on the water.  Membership fees for the Adult program for those are also reasonable, and give you unlimited classes and unlimited access to the boats from April 1 through October 31. 

Insider Tip

If you're planning a visit to Boston and your children want to participate in this program while you're here, have them pass the 75-yard swimming test before you leave home and bring the required documentation with you.  You'll find requirements in the Handbook in the "Youth" section of the Community Boating website.

Essentials: Community Boating Boston

Location:  Boston Esplanade.  Use the Charles Street footbridge to cross Storrow Drive, take the left stairs down the footbridge, and the Community Boating boat house is straight ahead.
Nearest T station:  Red Line/Charles-MGH
Membership fees:  Kids, sliding fee based on family income; Adult fees also reasonable - see website for details
More information:  617-523-1038; website
Hotels near Community Boating:

  • Liberty Hotel - Near the Charles Street Footbridge - Rates/reviews
  • Beacon Hill Hotel - Few blocks from the Charles Street Footbridge - Rates/reviews
  • Wyndham Boston Hotel - Also a few blocks away - 5 minute walk to the Footbridge - Rates/reviews
Community Boating boat house in Boston Massachusetts, next to Charles River


Courageous Sailing in Charlestown Navy Yard

With a fleet of over 70 sailboats in all sizes, including large cruising boats, the non-profit Courageous Sailing Boston located in Charlestown Navy Yard offers one of Boston's best values with its sailing programs for kids and adults, day sailing options, and racing.

Courageous Sailing Center in Boston's Charlestowan Navy Yard
Courageous Sailing in Charlestown

Most adult sailing classes take only a weekend (Saturday and Sunday) to complete, making this a great excuse for spending the weekend in Boston.  If you need a customized curriculum, the staff is happy to discuss your requirements.  Although Courageous Sailing offers membership options, you do not have to be a member to take a course.

Memberships are reasonably priced, and range from 1-day to annual options.  The membership fleet is available for daily sailing from May through October, and frostbite racing continues through the winter. 

Courageous Sailing's kids' programs emphasize learning sailing and water safety skills, along with building leadership skills. 

If you are an experienced sailor visiting Boston for just a short time and want go explore Boston Harbor and the Harbor Islands, try the one-day option.  Not a sailor?  Not a problem!  Courageous also offers charters for up to 4 people - call ahead to reserve.

Essentials:  Courageous Sailing Boston

Location:  Pier 4, Charlestown Navy Yard
Nearest T station:  Orange and Green Lines/North Station (walk across the Charlestown Bridge)
Water Shuttle: Take the MBTA Water Shuttle from Long Wharf (Downtown) to Pier 3 in Charlestown and walk over to Pier 4
More information:  617-268-7243; website

Hotels near Courageous Sailing School:

Constitution Inn in Charlestown Navy Yard in BostonConstitution Inn - In the Charlestown Navy Yard, a short 4-5 minute walk to Pier 4.   Affordable rates and a great gym make this one of Boston's best bargain hotels.  Location also convenient to the USS Constitution, and just a short walk to Bunker Hill.  Rates/reviews  |  More about the Constitution Inn

Marriott Residence Inn in Charlestown, across from Boston MAMarriott Residence Inn at Tudor Wharf - Short walk to Courageous Saiing on Pier 4, TD Garden, and the North End.   Affordable rates for suites make this a top family choice.  Gorgeous harborside dining.  Rates & Reservations   |   More about the Marriott Residence Inn at Tudor Wharf


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