Where to Go Sailing in Boston

If you love sailing, Boston's waterfront location 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. 

You can even try frostbite racing.

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!

Top photo: Sailing in the Charles River - that's Back Bay and Hancock Tower in the background

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Boston Sailing Center

Headquartered 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!

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More to Ways to See Boston from the Water

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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.

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Boston Harbor Sightseeing Cruises

Tour Boston by boat - the best way to see the city!   Check out these fun sightseeing, music, and entertainment Boston Harbor cruises on the Yacht Northern Lights and Schooner Adirondack III:

 Popular Cruises

• Northern Lights Sunset Cruise - Grab a refreshments from the bar and then relax as you watch the sun set on this sail around the Harbor, just in time to catch the USS Constitution fire its cannons as the sun dips down past the horizon
• Brunch Cruise on the Northern Lights - Savor a delicious 3-course brunch on this relaxing sightseeing cruise around Boston Harbor
• Boston Harbor Cruise on Northern Lights - Soak up Boston's unique sites and rich history on this comfortable sightseeing cruise around the Harbor - perfect friends and family experience!  Food and beverages available for purchase at the bar

 Holiday Cruises

• Holiday Brunch on the Northern Lights- See historic sights and panoramic views around Boston Harbor with friends and family as you enjoy this relaxing cruise with brunch, hot chocolate, and holiday cheer - Book now
• Holiday Cocoa & Carols Cruise on the Northern Lights - Sip hot chocolate and treats as you listen to jazzy holiday favorites on this festive cruise - Book now
• Holiday Sunset Cruise on the Northern Lights - Enjoy gorgoeous sunset views over the Boston skyline, a cup of hot chocolate, classic holiday hits as you cruise on the festively decorated 1920's style yacht around Boston Harbor - Book now
• Gift Card - Give the perfect holiday gift!  Shop now

New Year's Eve & New Year's Day Cruises

• New Year's Eve Cruise - Say goodbye to 2024 and welcome 2025 on this elegant Boston Harbor cruise with fireworks, live music, and gourmet appetizers; purchase the beverage of your choice onboard - or pre-order a bottle of Moet & Chandon when you book - Book now
• New Year's Day Brunch Cruise - Welcome the New Year with a tasty hot 3-course brunch on this relaxing sightseeing tour around Boston Harbor - perfect start to the New Year! - Book now
• Gift Card - Give the perfect holiday gift!  Shop now

Valentine's Day Cruise

• Romantic Valentine's Day Jazz & Champagne Tasting Cruise - Toast your valentine on this romantic evening cruise as you sample 3 champagnes and nibble on chocolate-covered strawberries while a live jazz band plays in the background.  Capacity is limited, and these special cruises always sell out early.  February 14 and 15

 

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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.   

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.

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. 

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Boston Hotels with Outdoor Swimming Pools

• Verb Hotel next to Fenway Park (shown in photo) - Find Lowest Rates
• Colonnade Hotel near Prudential Center - Find Discount Rates
• Revere Hotel in the Theatre District -Find Discount Rates
 

Find more Boston hotels with outdoor swimming pools 

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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.

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Courageous Sailing in Charlestown Navy Yard

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.

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Fun Things to Do and See in Boston

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