1. Classic Sail

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Boston, MA

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Classic Sail

4.9 (55 reviews)
Open • 8:00 am - 8:00 pm

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View of Boston
Wendy S.

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

Photos from our afternoon sail
Sally P.

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!

View of the city from the harbor
Rachel S.

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.

Charles C.

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!!!

Meg D.

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!

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!

Views from the boat is amazing! We decided to head out at 6:00pm (August) perfect weather and a beautiful sunset!

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Ask the Community - Classic Sail

Review Highlights - Classic Sail

“Captain Dave was easily in the top 3 in terms of overall experiences and how effortless the day felt.”

Mentioned in 23 reviews

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Narragansett Sailing Charters - Rich Munson & Jeanne LaChance, Co-Owners

Narragansett Sailing Charters

(1 review)

My adult-age sons and I just recently completed the ASA 103 Basic Coastal Cruising class at the…read moreschool. It was a really great experience. The class had just the right mix of some classroom and theory instruction along with a majority of our time spent on the water. I appreciate how much we repeatedly practiced the important and practical skills needed to operate a sailboat under power, including docking, standing turns, fueling, and more. We were also fortunate that our instructor, Captain Dave Pelkey, was in possession of vast sailing knowledge and experience, which he shared often, explaining the reasons behind everything we were doing, not only how to do it. I recommend the school to anyone seeking to increase their sailing knowledge and to get an ASA certification.

From the owner: Perfecting the sailing charter experience. We help you find the right boat and map out an…read moreunforgettable trip. Find Your Perfect Boat: We always have new and unique boats becoming available, including Catamarans, which are hard to find in New England. Map Out An Unforgettable Trip: Start out from a protected cove in Narragansett Bay with every amenity you will need before your trip available. Set sail through Narragansett Bay or head up to Martha's Vineyard. The beauty of the Atlantic and historic New England is special from a sailboat! Reserve Your Boat and Get Ready: It's our job to make sure you have a wonderful experience, from start to end. The boat will be in an individual slip to make loading quick and easy. Our staff will help everyone get comfortable with the boat. All boats are impeccably maintained so they are always ready to set sail when you are. Contact us or book online today.

Courageous Sailing - Our Youth Program kids set sail

Courageous Sailing

(42 reviews)

Charlestown

All about Sailing! Great People which focus entirely on…read moreteaching people how to sail and how to get better and better. CSC is an NPO dedicated to learn Bostons Children to sail. CSC has an extensive adult program, too. It's right there at the Navy Yard and you Sail in Boston Harbor and the Harbor Islands (depending on your flag rating). I enjoy coming down there to relax, de-stress and having fun! Thank you all from CSC for being there!

If you are an adult looking to learn to sail you have much better options, Please don't waste your…read moretime or money at Courageous Sailing. If you want to learn the basics of sailing at a fraction of the cost of courageous just check out Community Boating on the Charles River, it is only $275-445 for the entire year. With this you will have access to Mercury, laser, 420 (race boats), ideal 18, sonars & windsurfing. With courageous the learn to sail is scheduled for 2 weekends (4 days) with Community the classes are being held all the time and you can take them whenever you want, so you can avoid cold rainy days, and take the classes with different wind conditions (light, med, high) as many times as you want for no charge, unless its an advanced class which is only $50. When I took my learn to sail at courageous it was cold, rainy with fairly large waves. One of the people I took the class with actually started to cry. This is a non issue with Community because if the conditions are awful just come another day. After 1-2 years at community, if you like sailing you can go to a real adult school if you want to level up your sailing skills. Note the internal ratings at community and courageous have little to no value at other sailing organizations. If you are serious about sailing you need to build up your ASA certifications especially ASA 101,103 and 104, there are many ASA schools and you can take classes at different schools all across the country, Caribbean & world. Once you are ASA certified these credentials will follow you to other ASA schools & organizations. Once you reach ASA 104 you can apply for a type of international license. Also note that community has a much nicer facility and dock with actual restrooms with a shower. At Courageous they have portable toilets, no shower and 2 outdoor sinks which almost never have soap. These are the same sinks the staff preparing the cookout food uses. Also note that the traffic on the Charles is much safer vs the harbor, in the harbor you will run into huge tug boats and huge freight ships. On the Charles the boats need to pass under the bridges, so the biggest boats there are duck boats and some small/medium sized tour boats. Actual ASA alternatives to Courageous are First Reef Sailing in East Boston, one of the owners is Capt Paul Sullivan 5 time outstanding ASA instructor, they have the best learn to sail boat in the Boston Area Colgate 26, unlike Courageous the motors actually work & are reliable. If you are a student you can get a Colgate membership for 2K which I think they allow you to share with other members so better boat & may be less expensive vs Courageous also once you achieve 104 status (can do in one year) there is no range limit you just need to be back by sunset. They also offer memberships on cruisers & catamarans, these cost more like 10 K but you can also share those memberships. These are new boats almost everything works on them unlike courageous, And you can go on multi day to week long trips. Another ASA alternative is Reef Runner in Friendship Maine, one of the instructors there is 4 time outstanding instructor, its pretty close to Arcadia National Park. They are less expensive than Courageous and they quality of the instruction is vastly superior. Once you pass a class in an ASA school your log book will be signed by the captain, you will also receive an official stamp for your log book from ASA and the results will be uploaded to ASA so all other ASA organization globally will see your rating. Another tip is no matter where you sail keep a log book on the miles & a brief description of the trip

Frayed Knot Sailing Charters - Capt. Claude Beaudet & First Mate Judy
Photo By Nicholas Beaudet

Frayed Knot Sailing Charters

(10 reviews)

The Frayed Knot is a family owned and operated charter; Capt. Claude along with his wife and first…read moremate Judy are both experienced sailors. I reserved an evening cruise for a surprise engagement and they were both very interesting, polite and welcoming people. My guests were blown away by the experience and I hit it out of the park with my surprise, my fiance loved it. I spoke with Capt. Claude before hand and even though I didn't need to ask for much I felt that they were welcoming and would do anything to make the experience a memorable one. Even a last minute request made within reason was accomodated. First of all the boat is beautiful, and it's big and I think that 6-10 people could comfortably enjoy a cruise with out feeling cramped. Every one of my guests were excited and comfortable. ..light snacks were provided and drinks were made available even though this was BYOB. Don't worry about utensils like I did, there were glasses for the toast and champagne had i forgotten to get some. I will spare no praises in saying that they certainly made this experience as easy as possible for me and I appreciate it.

Our whole group would just like to send a huge thank you to Captain Claude and Judy for hosting us…read moreon the Frayed Knot for a spectacular afternoon of sailing a few weeks ago! Both Claude and Judy could not have been more kind and accommodating for our large family sailing excursion. The boat is absolutely gorgeous, spacious, and comfortable. Our hosts provided great amenities for our sail, were so wonderful with our 2 small children, who could not stop talking about how fun the sail was -- "best sail ever!" If you are looking for a spectacular, comfortable, educational, and above all, memorable sailing experience for your family or larger group, we highly recommend the Frayed Knot! We look forward to future family sails with Claude and Judy.

Adirondack III Sunset Sail

Adirondack III Sunset Sail

(10 reviews)

Waterfront

A MUST DO! A Beautiful Relaxing Sunset Sail of Boston aboard this beautiful white Schooner. We got…read moreDiscount Tickets @ Goldstar for The Schooner Adirondack III. Bring an extra Hoodie, it gets cold sometimes on the seas. When you arrive, bring your tickets to the office. You are then given an Adirondack Ticket. We boarded the all white vessel at daylight & the ship headed out from Rowes Wharf. Once they are quite a distance out they cut the motor & the ship sails on its own on wind power via its sails. You can see the planes taking off & landing from Logan Airport. This is a QUIET TOUR. The Captain & Crew are not tour guides talking every minute on a loud speaker. They Do Not Talk or point out Various locations. That being said You can ask questions which they will happily answer you. This Tour is meant for those who really want to Unplug from the Grid, & The Day to Day Stressful Lives of Modern Living & Experience a Relaxing Boat Trip & Nature. You can buy Wine & Beer on board but they give you Free Bottle Water. Feel free to bring your own snacks. There were lots of couples on board & some Single Friends too. It was so nice to see people not checking in with their phones every minute & just taking in Nature & interacting with Friends & Loved Ones. Everyone just used their Phones to take Pictures. They steered the ship in different directions so you could get some really great shots of the Sunset. They also gave out some blankets for those who were Cold! We finally sailed into Rowes Wharf as the Night fell upon the City. The reflection of the lights of the buildings on the water at Night was FANTASTIC! It was beautiful to see Boston @ 3 different times Daylight, Sunset & Nighttime. It was a 2 Hour Tour. They are all finished for the 2018 Season but they will reopen in May 2019. The Adirondack III is 80 feet long with a 16-foot beam. Her lines are modeled after an 1890s style pilot schooner. Adirondack III is long and lean with a spoon bow, which helps her ply through the waters much more effortlessly than the average schooner. It is an all-wooden vessel with a white glass overlay hull. The ship can hold up to 41 Guests. When you look above, you will find two towering Douglas Fir masts and nearly 2,000 square feet of sail stretching to the skies. They have a bathroom below deck too. It used to be, you had to have Mega Bucks & be really Rich to have the Good Life, not anymore. The Game has changed. You've been Upgraded. Now You Can Live Like a King on a Limited Budget

What a fantastic outing! We've been taking Adirondack III sunset sails for my (summer) birthday for…read moreyears now, and they just keep getting better and better. Within minutes of leaving the dock, it's like you're not in the city at all. The air is cooler and fresher, and you're out on the water (with someone else - or two someone elses - doing all the work)! The crew is professional and friendly - always offering to take photos and getting us our prosecco (hey, it's my birthday) promptly! Seeing the harbor islands, the other boats, and then the Boston skyline all lit up by the sunset behind it is just a peak experience! In fact, I'm thinking we should do this more often...

Classic Sail - boatcharters - Updated October 2026

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