This was one of the highlights of our trip to Boston! The…read morecrew was incredible to watch as they worked the sails. The deckhands were full of energy, especially Alex--you could tell he truly loves being out on the water. He also took the time to point out and explain the landmarks we passed while sailing around the harbor. I can't recommend this experience highly enough!

The day sail was awesome! Kira and Alex were so nice and really knew what they were doing. The…read moreservice was quick and exceptional. I would definitely come back on this boat! They made the ride fun :)

We were guests for a wedding aboard one of Anitas boats last night. It was perfection! A lower…read morelevel with dance floor, seating, food and a fully stocked bar. Upstairs, where the ceremony was held, had beautiful views of the Boston Harbour. Both levels had clean restrooms :) Anita greeted everyone on the dock, and flawlessly coordinated the music. A lot of details can be lost, but I can't think of one Anita missed. I highly recommend.

When i booked that charter in February - i was told we would have music for the charter to hear…read morethe concert- we would have a buffet and the boat seated 25- 30. It took 6 emails and calls to get corect directions t for the pick up dock - NO MAP...the boat has 43 people on it the upper deck steps said 5 adults only there were eleven of us - 7 tanding to eat because there was no seating. the food was marginal - we a choice of water or cans of pop. There is no way there were 43 life rafts for any emergency - people from California Colorado were also dumbfounded- Do not take this charter -

Captain Dave is the kind of guy that not only oozes knowledge of sailing, the route, and…read moresurroundings 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!!!

What a great experience! We sailed with Captain David on a beautiful day in early May. Because my…read morepartner 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!

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.

I mistakenly bought tickets for the wrong day and they made it super easy to move the tickets to…read morethe day we came. It took five minutes and we made it on the boat! The tour guide was very enthusiastic and knowledgeable which made the entire experience more rewarding. We managed to see plenty of whales and had a blast! The food isn't anything special but there were some good canned drinks that I tried. Just eat before you come or bring something with you onto the boat.

My boyfriend and I went on this whale-watching tour together, and it became one of the most…read moreextraordinary experiences we've ever shared. We learned so much about whales, their behavior, and the marine environment, which made every sighting feel even more meaningful. We were especially fortunate because the whales were unusually active that day, and we even witnessed some rare sightings. Watching these magnificent animals move through the ocean was breathtaking, the kind of experience that makes time stand still for a moment. Beyond the excitement, the tour gave us such a beautiful and romantic day together. Being out on the water, learning, laughing, and witnessing something so remarkable side by side felt truly magical. We'll cherish these memories forever.

If you love sailing, appreciate history, and enjoy "life at sea" you need to book an excursion on…read morethe Fame or Liberty Star or both as I did! The captains and crew are great, and the feel and sights are excellent. Me and my walking stick were welcomed and helped every time I sailed with them over a period of six days while staying in Boston for the 4th of July!!! I could be a seriously be a stowaway. Read about each ship online, book your cruises and ENJOY!!! Photos: sail "with" the USS Constitution July 4th, reflection of our tall ship in the glass (sorry I do not remember name of building), the sails and rigging! Photo 1 in review by J Diane Farris Photo 2 in review by J Diane Farris Photo 3 in review by J Diane Farris

Summer break trip to Boston and of course we had to try the tall ship cruise by the Boston harbor…read more This is a 1.5 hours time cruising out into the harbor...passing the airport, terminal, Castle Island, and around the Spectacle Island. We went for the late afternoon time slot because it rained a little bit in the morning. Luckily no more rain in late afternoon and while the weather was cool and cloudy, we still enjoyed the ride. Nice view and relaxing. Our boat wasn't packed with people so I think that also made a difference where folks were spread out sitting around the tall ship. The captain and 2 crews were professional and friendly. They offered a complimentary drink if you would like one. Note that this is not a historical tour. But if you want a relaxing ride to enjoy the harbor view, give them a try.

The family and I had an amazing time on Artemis sailing with Captain Rick and his wife Deb. What…read morean amazing experience to sail on such a beautiful yacht and with such wonderful people. If you've never sailed or are an experienced sailor, you will truly enjoy this great experience and discover Gloucester and the surrounding area. This sailing yacht is super stable, fast and fun. Make new friends, new experiences and memories! Sail Artemis!

From the owner: Set sail for an unforgettable experience aboard ARTEMIS, a 65-foot high-performance sailing yacht…read moreoffering luxury sailing tours along the stunning coast of Gloucester, Massachusetts. Meal included. Maximum of 6 guests. Daysails, sunset sails and more. Enjoy 3-hour or 4-hour excursions for 1-6 passengers featuring breathtaking coastal views, smooth sailing, and farm-to-table meals that elevate your journey. Departing from Historic Gloucester, you’ll have the chance to explore ports like Marblehead, Salem, and Beverly, soaking in the beauty of New England’s waters. With 45 years of combined boating experience, Captain Rick & Deb Miles ensure a safe, comfortable, and truly special adventure. Whether you’re looking for relaxation, exploration, or an elevated sailing experience, ARTEMIS is the perfect choice. Contact us today to plan your custom voyage and experience sailing at its finest! Learn more at Artemissails.com

This boat is soooo fun ..what a great day we had sun was out and we ate and drank boating around…read morethe harbor for a few hours listening to music .we even got off at spectacle island for a little swim .. The captain and he's first mate couldn't have been nicer or more helpful..cannot wait to book again soon ..

HIS PICTURE WITH HIS SON IS TOTALLY MISLEADING-AS HE SON IS TALL & ATHLETIC AND IN HIS TWENTIES…read more.. Always trying to fool his clients....Older boats often having mechanical problems..Used to rent at Rowes Wharf Hotel boat docks..but they refused to let him use their facilities because he was using the hotel for changing and washing up,,Along with excessive use of docks by piling up all his boat equipment on the private docks which was not allowed and getting a lot of complaints about his temper tantrums which we all experienced..Never go out with him again...Has a personality problem..Tried to pick up the younger woman on our trip as well...Beware...he has parked his boats now illegally along the Aquarium Dock,,,,

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.

Spirit of Boston Company, REVIEW: August 7, 2026 dinning…read moreexperience. I am writing to provide feedback regarding my recent dining experience on the cruise this past Friday. First, the table layout requires attention. Tables should not be placed near the entrances or exits, as this positioning lacks privacy and allows passing guests to crowd those dining. We requested a table change, and the floor manager promised to move us once a table became available, but she never followed up with us. Second, the food quality was disappointing. The steak was tough, and all of the food, including the steak, was served at room temperature. Additionally, the dinner rolls were cold, making it difficult to spread the butter without tearing the bread. Third, the service was severely delayed. Our waiter took our order but did not return with our drinks until I reminded him 20 minutes later. We could see our drinks sitting at the bar during this time. Overall, I would rate the service a 6 out of 10, and the food a 7 out of 10. On a positive note, the DJ was outstanding. The music selection appealed to everyone and created a wonderful, inclusive atmosphere where all the guests enjoyed dancing together. The entertainment easily deserves a rating of 10+. I hope this feedback helps improve the dining experience for future guests. Best regards,

Went on my first dinner cruise with my husband to celebrate our upcoming wedding anniversary and it…read morewas wonderful! Our server Jane was very nice and made sure we had everything we needed as our set meal choices were brought to us. The presentation of the food from the appetizers, entrees and desserts were well presented. We had the opportunity to explore the open view area of the ship to get some great pictures of the skyline and photos of us too. The staff around us were all friendly and had smiles too. As we left the two hour cruise they offered a treat to leave with (a cookie) but we were both full from everything we had already served us. I would definitely do this again.

Spectacular views of Boston with just the right vibes. For a cruise, it was fun but as a dinner…read morecruise, it wasn't as impressive. We boarded at 4pm and immediately went straight to dinner. I wished they mentioned it because we thought they would serve dinner after they sailed. Our server was nice and attentive. Food was okay and nothing to really boast about. We ordered jumbo shrimp cocktail but I guess it shrank on the way to our table. We were able to explore the boat though after dinner and soaked in the views. Overall, a fun experience but too overpriced for what it was.