Captain Dave is the kind of guy that not only oozes knowledge of sailing, the route, and surroundings on your trip, but he also fit into to group seamlessly and doesn't feel like an outsider... and that makes it feel like you're on the water with a bunch of friends and one just happens to own a boat. First, we had to reschedule our trip from last year as I was hospitalized and unable to make the original trip. My wife contacted Dave and they refunded us initially without hesitation. These are not only professionals, but people with kind, large hearts. The policy could have easily taken our money but we were able to reschedule and not have to pay any additional fees or money given our extenuating circumstances. The boat is clean, well-kept, and the comms and instructions were passed along early and with plenty of detail to leave no room for misinterpretation. Payment and scheduling were easy (as my wife told me, at least) and expectations were set as to what was (and was not) provided in the cost. As far as the value and trip itself, it's money well spent. We've done dozens of chartered routes along the coasts as well as in the Caribbean when we travel. Captain Dave was easily in the top 3 in terms of overall experiences and how effortless the day felt. It wasn't too long or too short, and Dave made sure to capture plenty of moments and memories for us instead of all our photos missing one (or more) members of the group. We also got to stop at 2 of the islands and swim around for a bit at each of them before returning back to the docks. There were 6 people in our group and we had plenty of space for all of us, 3 backpack/YETI soft coolers, and about 4 bags of food/snacks. There is also a shaded area if you forget sunscreen and/or just need to get out of the wind or sun. If you're curious or wondering if you may enjoy an experience like this, my best advice to you is just book it and don't overthink it. It surpassed all my expectations and was a blast of a way to spent a hot, sunny Saturday in the summer. Given the other reviewers' experiences, it doesn't seem like anyone has had a bad experience with any of the captains either. If you have anywhere near the experience I did, you'd be okay with paying double what we did for the day... it's just that much fun. Thank you to everyone at Classic Sail for the kindness, understanding, and above all - the awesome product/experience. You've made a few new fans in the Boston area!!! read more

What a great experience! We sailed with Captain David on a beautiful day in early May. Because my partner has such a strong desire to learn to sail, he asked a lot of questions to learn about the vessel and different verbiage. David enthusiastically answered every question, while also giving us lessons on different sights around the sail. Highly recommend - hope we can make it back another day! read more

Classic Sail - Boat Charters Near Me - Boston, Massachusetts

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Amazing! So fun! Saw parts of Boston that we wouldn't otherwise see any got to raise the sail!

This was probably one of the best days I can remember. If you are just contemplating doing this, do this! You will not regret it! And use this company, family owned and operated with someone who is the epitome of achieving their dream! The boat is wonderful and his own labor of love. We had an exceptional day of weather on our four hour journey out to the Boston islands. As a family now of six with the addition of my two daughters-in-laws, we have traveled the world together and everyone agreed this will be a memorable day we will all cherish. I wish Captain Dave much success and am grateful for his expertise and passion! Don't go with some corporate entity, go with someone who truly loves what he does. read more

Spent the morning and early afternoon with David on a private charter with my wife for my birthday. Though the wind was light the experience was full and informative. The Skip Jack is awesome and truly unique. A wonderful surprise and experience. read more

Nice evening and very informative about history of city and how the ward was transformed, fun night out with my husband read more

Classic Sail - View of Boston - Boat Charters Near Me - Boston, Massachusetts

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We booked an afternoon private sail on a sticky July day. We met David and proceeded to have a relaxing and informational inner and outer harbor tour. David is knowedgeable, friendly and clearly an outstanding sailor. We were super thrilled to have him as our captain. I booked the entire tour online and Classic Sail was responsive and responsible. We met David at the appointed hour and jumped right onto the boat. I highly recommend him and the tour for a fun and unique way to experience Boston. Thank you so much! read more

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Such a lovely way to spend the afternoon! We were a group of 6 friends and did the two hour charter. There was plenty of room onboard the beautiful boat, gorgeous views and David was great. Loved every minute. read more

Classic Sail - View of the city from the harbor - Boat Charters Near Me - Boston, Massachusetts

Not sure what to say but the boat ride was good enough, small and quaint the owner and deck crew were nice.

The Captain and crew were wonderful. From booking to sailing to the return to the dock. They were knowledgeable and attentive. Would definitely recommend and am considering going back for the 4 hour sail. read more

What a wonderful tour and a great time. Captain David was wonderful, so kind and so knowledgeable. My son is 15 and he has been sailing for a couple of years now. Captain David really took him under his wing and gave him so much knowledge and experience. We appreciate that so much. We had an amazing 1/2 day charter on the Captiva we sailed out to the harbor islands and our son and the Captain even took a VERY CHILLY swim. Beautiful day and we would highly recommend Classic Sail Boston. Thank you!!! read more

We were in Boston the last week of June 2024, and wanted a private tour of Boston Harbor. The 2-hour tour on the Captiva (the 45-foot Skipjack) was truly perfect. It was just our family of 3 and Captain David. It was also a gorgeous day to be in the Harbor, and he took us to see all the best sights. He even had our son help him with the sails and it was a blast. As we did the car and walking tours around Boston, the sights from the Harbor gave an even better perspective. This is a must-do if you are ever in the Boston area! read more

Classic Sail Boston is a fantastic way to have a special date. The sailboat is beautiful and David, the captain, is very knowledgeable/helpful/easy going. I will definitely be booking again. read more

Hi, Thanks in advance for reading. Had such an incredible surprise proposal on David's boat! I was deciding between Classic Sail and another local charter for our special day and am so genuinely happy that I chose to work with David. The Yelp reviews speak for themselves. David is all about customer service and wants his clients to have a memorable trip. Earlier in the day David accommodated me by going along with the surprise (pretending my client could no longer attend the sail) and had me drop off cheese, wine, and champagne at his residence. Had such an incredible time and recommend David wholeheartedly. You will not be disappointed. Finally, the boat is beautiful and you're able to walk around which is the cherry on top. Thanks, David!!! read more

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Really great night out with the girls. This is where we got started before dinner and then drinks. The staff was great and very accommodating. They offered champagne which was great. I would recommend this to anyone looking for a great night in the harbor. read more

This was most definitely the highlight of our Boston trip! So much of this town is walking and exploring... which has its merits... but I can't think of a better, more relaxing way to see the shoreline of Boston! Captain David made our trip so exclusive, fun and adventurous! We started out on a two hour tour at 10 in the morning... brought our own snacks, booze, and music. After loading up and launching off, we took a tour around the harbor, seeing all the sights, dangling our feet off the side and learning a little bit about how to sail! We got to see a closeup view of a extravagant yachts and the historic ships in the Navy Yard. This tour was amazing... 2 hours of relaxing fabulousness that we we're sad to see end! Highly recommended for anyone who wants to see Boston from a completely different and relaxing perspective! read more

Classic Sail - Boat Charters Near Me - Boston, Massachusetts

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What an amazing time we had for a 2 hour sunset cruise. Captain Dave was friendly, knowledgeable and created a fun and relaxed atmosphere. His sailboat is beautiful and plenty big enough for 6 of us. We couldn't have asked for a more beautiful night celebrating a birthday. We will definitely be sailing again! Thank you so much for a wonderful evening! read more

Classic Sail - Boat Charters Near Me - Boston, Massachusetts

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We had a rare couple of hours away from a busy conference and loved getting out on the water with David and his gorgeous boat. We wished we'd booked the half-day sail in retrospect, so when in doubt, book the longer tour. David let us "help" sail and was a most gracious host. read more

Did a 2 hour sunset charter and will never do again. This sailboat didn't feel safe the bathroom was dirty and captain Dave was by far the worst captain I've ever dealt with on a charter. Don't waste your money on this sailboat there are a ton of better options on the harbor. Stay away from this sinking sailboat. read more

Amazing experience on with Classic Sail Boston. Highly recommend for anyone interested in a special outing on Boston Harbor, a truly unique and special experience. Booking was very easy and seamless - their website shows all of the available times and pricing. There was plenty of communication leading up to the trip. Captain David was great day off, making the trip super smooth. We brought wine, cheese, and crackers which really topped off the experience. read more

Excellent views! The captain David was super friendly and the whole experience seemed so natural! Been on so many motor boats around the world - Africa, Asia ... But being on a sailboat is completely different!! Can't wait to bring my family on the tour soon! read more

Classic Sail - Views from the boat is amazing! We decided to head out at 6:00pm (August) perfect weather and a beautiful sunset! - Boat Charters Near Me - Boston, Massachusetts

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We did a half day boat ride with Dave. We had a great time. The weather was great and because of the longer time we got to really see Boston from the water. We did a similar half-day boat ride last summer in a different city, so I have that experience in the back of my mind as I am writing this review. The reason for the 4 in stead of 5 stars is because that boat was a little bigger and better accommodations. If I hadn't had that experience first I would give this 5 stars. There isn't anywhere really comfortable to sit, so I would highly recommend you bring towels/blankets (we didn't since we were traveling and our AirBnb didn't have them) so the deck was pretty hot. Also Dave says he has soda and refreshments, but really it was whatever he had in his own personal cooler. I would have preferred the description say bring absolutely everything you want because the captain won't have it. There is a bathroom, but it's not a full bathroom with a door, not a big deal, just something I didn't know ahead of time. Overall it was a really nice day. Dave was professional. I would recommend him to others looking for a simple day on the water. if you're looking for something a little fancier, this boat might not be it. read more

Fantastic time out on the water!! Captain David is very knowledgeable and gave us a relaxing experience out around the islands near Boston. 10/10 recommend read more

We had the best time today going out on Classic Sail Boston's sailboat Captiva. I decided to book the charter for my husband and father-in-law for Father's Day. As soon as we arrived on the boat, David immediately made us feel comfortable, gave us the history of the boat, and asked what we wanted to do during our charter. We had our 9 year old son with us. Dave included him in all aspects of manning the boat and answered his dozens of questions. Our son had the best time, and was super sad when our 4-hr charter ended. Overall, my entire family truly enjoyed the charter- truly a testament to Dave's welcoming personality. We will definitely be booking again soon! read more

We had one of the most amazing nights in Boston on the Nanatasis with a crew of two, Captain Craig and Kyla. The boat is beautiful and well-kept. Craig was so friendly and immediately made me feel at ease when I expressed concern about getting seasick (which I did not). Kyla memorized all of our names and was very attentive to our needs. The night really lent itself for a twilight sail. The sunset was absolutely breathtaking and the ocean was calm enough for a smooth ride. We would definitely recommend Classic Sail to anyone looking to charter a sail boat. We plan on making this a yearly tradition! Thank you so much again, Craig, for making our night so memorable. read more

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We had a great time sailing for my dad's 70th birthday celebration! Captain Dave was an excellent sailor with a lot of knowledge about the harbor. Would recommend this to anyone looking for a unique experience in the city. The boat is beautiful and everyone in my party enjoyed this cruise around Boston harbor. Thank you for making my Dad's birthday so memorable!! read more

Classic Sail - Boat Charters Near Me - Boston, Massachusetts

Cannot recommend Classic Sail enough! Dave was an absolute delight - not only did he accommodate rescheduling and tough schedules to work around, he was really a joy to be around. Since it is small quarters, the captain can really make or break a trip and he definitely just enhanced the experience. SO much fun :) Thanks Dave!! read more

Can't say enough good things about captain Dave and his wife. Our girls trip wouldn't have been complete without our sailing trip. They supply everything from cups and ice to water and a wireless speaker for our music. Captain Dave found us all the best photo ops (which was key) and was great to chat with. Would highly recommend. Can't wait to come back! read more

Classic Sail - Boat Charters Near Me - Boston, Massachusetts

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What a great day! Beautiful boat and amazing captain! My 86 yearly old gma loved it:) She had open heart surgery this year- if she can do this, anyone can! It was a smooth sailing fun day. Thank you so much captain Dave! read more

Classic Sail - Best Father's Day! - Boat Charters Near Me - Boston, Massachusetts

We had the best experience on Classic Sail with Captain Dave. The boat was gorgeous and we learned so much about the Boston Harbor, the history of oyster catching and their unique boats, ocean conservation and info about the local area. Dave was great with our kids and involved them in hoisting the sail, steering the boat and engaging with them throughout the trip. We were able to bring dinner on the boat and enjoy the beautiful harbor in a fun, laid back, informative and memorable way. Many, many thanks to Dave for making this such a great experience. We definitely recommend it. read more

Classic Sail - Boat Charters Near Me - Boston, Massachusetts

If you are looking for a sailing tour in and around Boston, look no further--Classic Sail Boston is your best option! From the time you first talk to Katie, to the end of the trip, the service was incredibly friendly, helpful and responsive. Their sailboat is a classic with plenty of room to enjoy the day or evening regardless whether you are two or six in your party. David is a wonderful skipper who makes the trip interesting and fun regardless of the weather conditions. I cannot recommend more highly this family owned business--you will have a wonderful day! read more

By far my favorite thing I have done living in Boston for the last 2 and a half years. We had some incredible views of downtown Boston, and awesome swimming stops around some of the islands outside the harbor. Not to mention, the boat is so beautiful. Captain David is an amazing guide, and made the entire trip so much fun! He has a gift for sailing and entertaining, and I didn't want the cruise to end! I couldn't have thought of a better way to spend my birthday with friends! If you are considering a harbor cruise definitely choose Classic Sail Boston. read more

This sailboat ride was hands down our favorite thing we did while in Boston last week. Captain Dave and Lana were awesome guides and great conversation; very knowledgeable about the harbor, history, etc. Our family of 6 thoroughly enjoyed the 2 hour sail and took snacks and drinks along. Thank you for a wonderful experience! You are very good at what you do! read more

We had an amazing experience aboard this gorgeous sailboat! The beautiful boat was spacious and very enjoyable. Captain Dave was extremely knowledgeable and very accommodating. I would highly recommend this experience when in Boston! read more

Wonderful experience for my dad's 80th birthday present. The boat is beautiful and Dave is terrific. We all had a blast.

This was our second time cruising on the sunset cruise. 4 years ago, I proposed to my wife. This time, we invited two other couples. The weather was perfect. The captain is entertaining and accommodating. He maneuvered through the regatta and handled the rude boaters like a pro. We will do this again! read more

I have booked this 3 separate times and will definitely be back! Each experience has been amazing. Dave is extremely nice, accommodating, and very flexible with whatever your group is looking for on the trip. Will be back soon. read more

My daughter and a few of her friends celebrated her birthday last weekend on a Classic Sail Boston sunset cruise and they had an amazing time. Though it's only been a few days since their outing, they're already planning their next charter trip. David made such a great impression on them and ensured they had a memorable experience. I'm so glad that we chose Classic Sail for my daughter's special day. I'll make sure I'm on the boat for our next charter! read more

Wow, I truly cannot say enough good things about Classic Sail Boston. My sister, mom and I booked a sail a couple of weeks ago for Mother's Day, and it was perfect from start to finish. We had originally booked it for a Saturday during the day but it turned out to be a yucky, rainy day. Captain Dave was super accommodating and fit us in for the next day (meaning he had to drive from a family function and come meet us. Seriously. He's the best)! We ended up with a beautiful, sunny day to enjoy out on the water. Captain Dave was so friendly, and he talked with us the whole time! Not to mention offering seltzer, blankets, a bathroom and anything else we might need while on the boat. The sail was itself smooth and the view was incredible. Every second out on the boat was beautiful. The thing that separates Classic Sail from other companies is truly the customer service. Dave really cares about getting you out for a sail that will make you love sailing, not about just booking your sail whenever and taking your money. You can tell he truly loves what he does, and he does it so well. We will undoubtedly be back for another sail! read more

I found Classic Sail Boston from their website and called them to propose to my girlfriend while sailing on Boston Harbor. It was perfect--literally perfect. They were terrific--they offered to bring anything I needed so that the surprise wouldn't be ruined, so they brought red wine, three different kinds of cheeses, green olives, and crackers for us, at my request. They also brought blankets in case we got cold and a bluetooth speaker so I could play a music playlist from my phone. The boat is also perfect. It is a classic, restored sailboat in beautiful condition and it is incredibly romantic. It is also the perfect size so that you can share the private moment but also be on a boat that is a romantic and intimate size. Dave and Craig were warm and friendly, and extremely helpful. We set up a cue and they timed it and positioned us perfectly, and then took pictures from the back of the boat while my girlfriend and I shared the private moment out of earshot at the front of the boat. My now fiancée described it as "perfect, I couldn't have imagined anything better". We both loved it! Afterward, they took more photos as well and sent them to us. We were so thrilled with them and the boat, we will probably go out on it with them again. It was perfect. I wish I could give it higher than 5 out of 5. read more