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    Courageous Sailing

    4.7 (41 reviews)
    Closed 10:00 am - 8:00 pm
    Updated 1 month 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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    15 years ago

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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!

    Mentioned in 4 reviews

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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.

    Trinacria Fishing & Cruising Boston - Nice Fish

    Trinacria Fishing & Cruising Boston

    (4 reviews)

    North End

    Captain Riccardo and Judah did a great job with us. They worked hard, got us on fish and scored…read more Awesome job, looking forward to getting back on the water with Trinarcia again. Thanks for a great day on the water.

    I get nervous in the water whether it's on a boat or swimming...only because I can't swim and I…read morehave anxiety. My family and I had so much fun on Rick's boat. His boat is clean and steady. We went lobster fishing. The boat is so steady, it wasn't rocking around too much. Rick gave us each a job to do. One was to record how many lobsters in the trap, which were keepers and which we had to throw back because it was either female (breeder) or too small. I had the job of measuring the lobster for size. Rick taught us that if it's a breeder, you clip the tail to indicate that it's a breeder. My sister in law was recording the number caught in each trap. My brother in law helped with steering the boat (he has a boat too.) My husband helped with gathering the lobster trap with a pole. I didn't know pig skin is used as bait. Although I was nervous, Rick kept me busy with putting bands on the lobster claws. I became an expert at it. At the end of the day, Rick put our catch on the grill. Let me tell you, grilled lobsters are the best! Especially when it's fresh out of the ocean. There was also a small crab in the catch too. I had forgotten about being nervous in the boat. Definitely book a trip with Rick, he makes boating fun! Even for people with anxiety being in the water. I want to go boating again with Rick this summer! I'm not anxious with Rick. He's great! Maybe this time I'll learn to fish!

    Courageous Sailing - boating - Updated June 2026

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