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    Annapolis Sailing School

    4.7 (51 reviews)
    Open 9:00 am - 4:30 pm

    Services - Annapolis Sailing School

    Boat charters

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    Getting a little lesson at the helm from our awesome captain
    Eric F.

    I took Annapolis Sailing School up on their new "Evening Sail" option this past weekend, and boy was it a blast! We got a couple of friends together and loaded up a cooler full of drinks (BYOB) and dinner food, and set sail under the twilight sun. The cruise lasted roughly 3 hours and our captain took time to teach us little nuisances of both the Bay and the boat (Beneteau 37) we were sailing on... I highly highly recommend this excursion and will be back to take advantage of this, and the other options offered at Annapolis Sailing School in the very near future! Thanks again Captain John!!

    View from the classroom to the boats and boat dock.

    I can't say enough good things about this place - but I'll try. Last week I had basically no sailing experience whatsoever, and just completed their 5-day Basic Keelboat Certification class. I had two wonderful instructors: John & Gary. I'm not qualified to judge their sailing skills, but they're both great teachers - which is even more important. They're very knowledgeable about all things saling, and have the patience and temperament necessary to the task of teaching novices. Everyone at the school was incredibly friendly and helpful. The instruction was appropriately paced, blending classroom with hands-on sailing. When I finished the class and got my certification, I joined their "keelboat club" - which will allow me, for a flat fee, to rent a boat (availability guaranteed) on 72-hours notice, anytime I want, for the next year. I got a 10% discount for signing up shortly after completing the class. Pointers: While they have 3-day classes covering the same material, I personally felt I needed every bit of the 5 days to reach a point where I would even consider taking a boat out on my own. Others probably feel differently. The incremental cost of the additional days makes it well worthwhile. Also, I imagine the bay is a zoo on weekends. I took a week of vacation and was glad I did. I also stayed in town (I live in Silver Spring) to avoid the exhausting commute back and forth. Read up in advance to get the most out of the class. The volume of information is pretty overwhelming. If you know the terms and basics going in, you'll be way ahead of the curve, avoid wasting precious time and get the most out of the actual sailing. As a caveat... I was extraordinarily lucky in that: 1) we had absolutely perfect weather all week; and 2) I was the only student in my class (I appreciated the fact that they didn't just cancel it).

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    3 years ago

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    4 years ago

    Hilary Ranney-Howes really is the best instructor you can ask for. Fair winds and following seas!

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    5 years ago

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    9 years ago

    Great sailing school. Knowledge and friendly instructors...you can't beat sailing in the Chesapeake!

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    Page 1 of 2

    Ask the Community - Annapolis Sailing School

    Review Highlights - Annapolis Sailing School

    My son and I took the Basic Sailor ASA 101 course here last weekend (early August), and we had a GREAT time.

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    Annapolis Electric Boat Rentals

    Annapolis Electric Boat Rentals

    (41 reviews)

    On April 5, 2026, I made online reservation for a boat at 10 AM April 6, and was charged $423 at…read morethat time. At 8 AM the following day, I received a voicemail, an email, and a text message from the company stating that they were closed Monday and I should not have been allowed to make a reservation via their own website,. Obviously there would be a full refund, and they were very apologetic. I never received the refund and contacted them twice more during the next six days. Today I received an email from Benjamin. Tiederman stating that I would only be refunded 50%, which would not be received for another five days. This is fraud and theft, Along with basic incompetence and lack of ethics. I had to eventually submit a charge back to my credit card company, which will cost them extra money in fines instead of doing what they stated they would do. I've never left a negative review on any site so congratulations Annapolis electric boat rentals.

    This was a great opportunity from start to finish. Reserving was easy, and during the process I…read moremade a change due to the weather and that was easy. Driving an electric boat was a first and it was easy. I've been boating since 2012 and driving this boat was not only easy but fun...and but the way despite sailing since 2012 I'm still slightly step above a novice. The Captain/owner is a great guy, professional, and thorough. I didn't think this was a thing for me where I would want to come back and do it again but I feel like I'll be back this summer. I highly recommend it! Great experience and the perfect way to celebrate a birthday.

    Wilma Lee Skipjack Cruises - More sunset

    Wilma Lee Skipjack Cruises

    (7 reviews)

    We took Wilma Lee out for our rehearsal dinner and had an absolutely wonderful time. Such a great…read moreway to show people Annapolis. The staff was fantastic, it's byob and food which worked out great for us. The pricing was also very reasonable, we were impressed with all aspects. Will certainly do again.

    We booked the Fireworks from the Bay cruise on the Wilma Lee. It was the best experience ever. We…read morehave done the other sailing cruise from Annapolis several times, but this was so much more enjoyable. The boat is a historic vessel, the crew is knowledgeable and friendly, and they really put in a lot of effort to make it an amazing experience. We boarded at 7:15 pm, received the safety briefing from the captain, and learned the history about skipjacks oystering on the Bay. The ticket price included drinks (a nice selection of beers, wines, soda, and hard seltzer). Music (oldies favorites) was playing. They had prepared little goodie bags that included swag like little pinwheels and glowsticks and a bagged snack. They also passed out individual small charcuterie boxes with skewers of meat, cheese, and olives, plus a separate container of tiny crackers. The captain let people help the crew unfurl the sail, and he took us way out to see a visiting frigate. There were views of the Bay Bridge and lots of other sights. Around 9 pm, the boat was back in position for a great view of the fireworks. There is nothing like seeing the fireworks from the water. And the ticket cost goes to a good cause--maritime education and preserving this unique vessel.

    Sail Away Catamarans - F. P. Helia 44

    Sail Away Catamarans

    (7 reviews)

    Chartered a catamaran for a week in Nov 2024 from Sailaway Key West. Booked in March…read more Unprofessional outfit: boat we chartered was not available, but an on paper good alternative was offered. Then the price of the crew was increased. Excuse was that the person who we booked with in March was no longer with the company. Lot of work to redo all the work we had done in March to find the charter we wanted - anyone who has tried to book one knows it's much smoke and mirrors, the same boats are rented out by different outfitters, everything is a little different between each and it's hard to get a full picture of total cost, and to compare apples to apples and not something else. Document every conversation and detail of what you agreed upon with Sailaway (or any other company) or they'll change the game. Arrived in Key was as agreed upon. Boat reeked of sewage. Captain had been on the boat for ten minutes several days before our charter, that's it. Said it reeked then too, but didn't do anything about it. Captain had almost no contact with Sailaway, it was the first time they worked with them. Captain ended up calling marina engineer and it turned out that half of the boat had not been pumped out. Additionally, the captain's cabin bathroom was broken, and the toilet didn't flush. You can imagine. It all got fixed but it was a stinky hassle and we started our charter several hours late. Sailaway overcharged us in their electronic system and ghosted us upon repeated request to resolve. Jennifer, owner of the company, acted unprofessionally and winged it to provide a charter boat and an ok but inexperienced crew she had never met, nor taken the time to get to know. It came out all right by helping out on the fly, but Sailaway was disappointing and there was no communication with, nor support for the crew from them either. The situation would have been salvageable if Jennifer had responded to our emails and calls to resolve the issue and accept feedback as we asked her to do. But she didn't, which leaves us with a bad feeling about her and her company.

    Keegan Smith has been absolutely incredible to work with during all the stress of planning a unique…read moreand fun wedding. He has anticipated our challenges and calmed my fears. We have not even held our charter and I feel compelled to write this review. Not only has Keegan handled my concerns as the bride, he has fielded questions from other members of our charter with ease. I am sure the charter will be amazing, and I will provide an updated review after the event, but I 100% recommend Sail Away Catamarans and ask to coordinate it through Keegan!

    Annapolis Sailing School - boating - Updated May 2026

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