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    Boston Harbor Sailing Club

    2.9 (14 reviews)
    Closed 9:00 am - 9:00 pm

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    Brendan M.

    This must be one of Boston's hidden gems. Did you know that for just $280 dollars you can rent a 40ft sailing boat (complete with engine and gas for easy navigation out of the harbour) for the whole day? So find a friend with a license and get down here. There are few things that can compete with spending a day sailing around the Boston Islands, especially at this time of year, when the water is not too cold for swimming.

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    1 year ago

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    2 years ago

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    2 years ago

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    7 years ago

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    20 years ago

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    11 years ago

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    18 years ago

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    10 years ago

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    16 years ago

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    12 years ago

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    11 years ago

    Disingenuous and misleading about vessel availability with memberships.

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    15 years ago

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    13 years ago

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    18 years ago

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    Ask the Community - Boston Harbor Sailing Club

    Boston Sailing Club compared to Boston Sailing Center? Any reason to select one over the other?

    Very different clubs. Go to BSC if you want to drink beer and mingle with other singles. They have a good racing program with a wait-list. BHSC is far better for cruising and day-sailing with family and friends. There's a good range of cruising… Read more

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    Boston Yacht Charters

    Boston Yacht Charters

    3.4
    (8 reviews)

    Planning a special event on the water? Don't look any further! Ann at Boston Yacht Charters was…read moreAMAZING in helping me plan a surprise private charter for my boyfriend's bday and our anniversary! Not only did she coordinate an amazing afternoon on the harbor with Captain Don on the Indiscretion, she became my Boston tour guide helping me plan the perfect trip and walked me step by step through transportation, restaurants, neighborhoods, live music venues, etc. She is a true Bostonian, LOVES her city and should be named Boston Ambassador Extraordinaire! Ann made sure we had our favorite snacks, champagne, glasses, etc. and Captain Don had a cooler full of beverages and even offered to cook on the grill for us while on our 3 hour trip around the harbor. We visited Boston over Halloween weekend 2021 which was late in the season to charter a yacht. Ann communicated with me almost daily leading up to the trip and worked with various captains to ensure I would be able to surprise my boyfriend with a special day on the water...we even worked together to move the timing of the charter during our trip ensure we had the best weather for our excursion. Ann met us at the dock, took photos and took care of all the details, making it a wonderful surprise, within our agreed budget and helpful in every way. Huge thanks to Ann for her OUTSTANDING customer service and genuine interest in helping me plan a day that my boyfriend (now fiance) and I will never forget, and a special trip that we will always cherish.

    Recently booked a company outing with Ann at Boston Yacht Charters and everything worked out great…read more We booked a 2.5 hour harbor cruise on the Timeless through Ann who coordinated everything for us and worked within our budget. All we had to do was show up at the dock. There was plenty of food and drink (both of which exceeded expectations) and the staff of the Timeless were extremely friendly and accommodating. This was our 3rd time working with BYC and i foresee us returning again.

    Boston Harbor City Cruises

    Boston Harbor City Cruises

    3.4
    (14 reviews)

    Took my husband on the Spirit of Boston the other day. It was his first time. The boat is huge,…read morethree levels! We arrived right before departure, they are very prompt so make sure you're on time. The buffet was good, lots of options! Certain dishes were bland, just need more seasonings. But overall I was stuffed! Desserts come after dinner is done. It has a full bar and live DJ for some dancing. We had a good time! It's definitely a Must-Do in Boston!! Parking tip - the closet garage is right across from the dock 155 Seaport Blvd.

    I recently took my visiting family on a Spirit of Boston Dining Cruise for Dine Out Boston, and the…read morespecial price of $55 per person was an absolute steal! The trip alone is worth more than $55, so the additional food was just a bonus. Based on the menu I saw online, I was expecting a 3-4 course meal, but I was pleasantly surprised to find that the dining experience was buffet style. This meant we got to sample a lot of the delicious food! My favorites were the salmon and the chicken, and for dessert, I really enjoyed the peach cobbler (not pictured) because I couldn't resist devouring it before snapping a photo. When the buffet first opens, people rush to the line and it gets a bit crowded. My tip: let the hungrier people go first to avoid the claustrophobia. We also purchased a margarita for two, which was so huge that the three of us couldn't finish it! We even got a margarita mug with the City Cruises logo as a souvenir. There was a DJ playing cool music while we ate, and the servers were fantastic, bringing us drinks and quickly removing empty plates. The best part was undoubtedly the nearly 3-hour cruise around Boston, where we got to see a lot of landmarks. My family loved it, and it will definitely become a tradition whenever they visit Boston.

    Boston Harbor Sailing Club - boating - Updated July 2026

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