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    Courageous Sailing

    4.7 (41 reviews)
    Closed 10:00 am - 8:00 pm
    Updated 1 week ago

    Services - Courageous Sailing

    Boat charters

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    Courageous Sailing Center Pier 4 Charlestown
    Michael O.

    Courageous is the best sailing school in New England for your money. Great community, dedicated staff, awesome youth programs and sailing lessons for all.

    Boston, sailing

    This place is amazing! I was visiting from out of town and wanted to sail in Boston Harbor. The staff were very helpful and got me sorted right away. I was able to rent a Rhodes 19, which gave a surprising smooth sail. I enjoyed each moment on the water. Whenever I come back to Boston or know anyone wanted to visit Boston and sail, I will point them to Courageous Sailing! Special shoutout to Emiliano who took great care of me during my time at Courageous. Btw, did you know this place is a stone's throw from the USS Constitution, one of America's first and oldest Navy Vessels. You have to check that out when you visit!!

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    6 months ago

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    2 years ago

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    2 years ago

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    5 years ago

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    7 years ago

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    19 years ago

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    16 years ago

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    8 years ago

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    12 years ago

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    7 years ago

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    10 years ago

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    10 years ago

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    8 years ago

    Friendly service. Went out for a private sail. I'm hoping to get spend more time out on the water with them!

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    16 years ago

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    11 years ago

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    7 years ago

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    11 years ago

    Great place to get a membership and sail on in the Harbor. Much more reasonably priced than other options.

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    11 years ago

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    12 years ago

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    10 years ago

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    8 years ago

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    11 years ago

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    11 years ago

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    11 years ago

    Dave Dilorenzo runs an incredible program here. If you're interested in sailing, check out courageous. They bring passion to the sport.

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    18 years ago

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    10 years ago

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    11 years ago

    Took my husband for his 61th birthday gift. The experience was awesome as was our instructor Rick!!

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    Review Highlights - Courageous Sailing

    Whenever I come back to Boston or know anyone wanted to visit Boston and sail, I will point them to Courageous Sailing!

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    Come Sail Away Now - Tupelo Honey

    Come Sail Away Now

    (26 reviews)

    Charlestown

    I selected this company based on good reviews, but wonder if things have changed during the…read morepandemic and encourage you to proceed booking with caution as my experience trying to get on the boat was terrible and they held 50% of my total payment illegally. We originally planned to set sail, however, due to inclement weather reports on the day of the charter, we jointly decided to reschedule for another time and did not set the reschedule date at that moment because my party size was large, 15, and I needed to repoll the group on another feasible date. My group worked together to select a reschedule date, which the company made for a Saturday. The Tuesday before, we found out that one of our co-workers has COVID. As a result, all of us were potentially exposed. Out of concern for the safety of the crew and captain, I reached out by text message on Wednesday to inform them of the situation and figure out how to proceed. My coworker who had COVID also tried to contact you to find a resolution but could not reach them by phone. We received an email stating they unable to reschedule on this charter, and could do a cancellation that would result in a partial refund. They did not offer the option to reschedule to a fee, and said short of canceling, the charter would be scheduled to take place on Saturday with full awareness of the situation I expressed. I responded saying that we would like to proceed with Saturday in this case. I again emphasized that we had been exposed, and they cancelled without calling or communicating. After repeated calls and emails from Saturday to Wednesday, and finally a warning to report to the FTC for poor business practice, only half of my payment was returned. Nothing in the contract allowed them to retain it. So- beware. If you book, make sure you are going and don't expect your money back if you need to make a change for anything reasonable like being honest about a COVID exposure

    This is a harbor tour on a sailboat. The summer of 2009 was their first year in business and they…read moredon't sail in the wintertime. The sail boat, called the Tupelo Honey, can carry up to 12 people. I'd lived in Boston for several years but had never been on a sail boat there. I had previously been on boat cruises around the harbor. We were back in town for a visit and I saw an advertisement for this harbor tour. I absolutely love sailing and wanted to try it out. I called a day before we hoped to go on a sail and asked if they had any times available. Generally, the cost is about $25/person. But because we didn't have a large group, only two of us wanted to go, there was a minimum price to take the sailboat out. That was $140.00, which was fine with us. We had an absolutely fantastic time! The captain and other crew member were very hospitable, friendly and really easy-going. They asked us if we wanted to stay near the buildings to see the scenery or to go further out into the harbor and let us make the decision. I would definitely do this again and it was well worth the money. It couldn't have been better. Call at least a day in advance to make sure that they have room to take you out for a sail. Their website says that you can take a T-Boat (affiliated with the MBTA subway, the T) to a nearby pier and walk.

    Charles Riverboat - An intimate surprise engagement aboard Happy in Boston Harbor.
 @jasoncoreyphoto

    Charles Riverboat

    (151 reviews)

    East Cambridge

    We had a good experience with charles river cruise in our recent trip to Boston. The boat dock was…read morenext to a shopping mall with access to restroom, dining options and various shops. The receptionist was friendly. The tour guide was phenomenal. Bearing a great, easygoing and a bit sarcastic personality, she was engaging, knowledgeable, funny and honest about her delivery. I learned a few things about the city and the famous schools from her personal opinion. Very steady and peaceful ride. Clean and well-maintained boat with a bar. Be mindful it's hot inside the boat with the scorching sun in PM so bring water, sun screen and hat, dress lightly. It was our second day in town our bodies still adjusted humidity and heat, I felt I was about to get a heat stroke. It'd be nice if they consider AC operated boat in the future.

    We took the 90-minute Charles River Tour Cruise on Friday, August 1st--our first time using Charles…read moreRiver Boat Company. The views were nice, but the experience turned sour quickly due to a lack of passenger care and extremely poor customer service. Halfway through the ride, we were filming the scenery at the front of the boat when, without warning, the captain blasted an incredibly loud horn as a "greeting" to another boat far in the distance. It was completely unnecessary, and the sudden, deafening sound startled everyone around us. I almost dropped my phone into the water. We went inside for the rest of the trip because we no longer felt safe or relaxed. Later that day, we emailed the company with our concerns and offered to send them the video showing exactly what happened. They didn't care. Instead, the Director of Operations, Gibson Cushman, dismissed our complaint, quoted Coast Guard rules (irrelevant in this case), and refused a refund. He offered a credit for another cruise, which felt like a cop-out since we're not local. His response made everything worse--tone-deaf, defensive, and full of excuses. He even tried to blame us, saying passengers should expect loud horns at any time. I had ringing in my ear for 48 hours--if we'd known something like this might happen, we could've worn ear protection. Overall, it was a stressful and disappointing experience. Their focus clearly isn't on guest satisfaction or safety--only on covering themselves. We won't be returning and wouldn't recommend them to others.

    Courageous Sailing - boating - Updated May 2026

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