Cancel

    Open app

    Search

    Waypoints Annapolis

    1.0 (1 review)
    Closed 8:30 am - 5:00 pm

    Services - Waypoints Annapolis

    Boat charters

    Waypoints Annapolis Photos

    You might also consider

    Recommended Reviews - Waypoints Annapolis

    Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
    Yelp app icon
    Browse more easily on the app
    Review Feed Illustration

    5 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    Ask the Community - Waypoints Annapolis

    Verify this business for free

    People searched for Boating 837 times last month within 15 miles of this business.

    Verify this business

    Annapolis Sailing School - At the dock with the training boats.

    Annapolis Sailing School

    (51 reviews)

    Stop thinking about it and just do it…read more Def a top flight sailing school in the Mid-Atlantic! I did the combined 101/103 course that allows you to take out a cruiser. The 101 course is great for newbies; the instructors are all highly experienced yet very patient with beginners, you'll have a great time for sure! Since I love cooking, I'm going to use the Scoville scale to compare 101 and 103. If 101 is just a mild bell pepper, then 103 is a jalapeño. Don't take it unless you're ready for a true sailing boot camp! It will kick your ass, especially if you've just come from 101, but you're going to learn A LOT that you can then take with you to digest and practice. You're going to be overloaded with a LOT of information, but just take some time at the end of each day to decompress and process what you've learned and you'll do fine. They are all very passionate about the art of sailing and push you hard to be the best sailor you can be. Def a great experience!!!

    I wanted to update my review of Annapolis Sailing School. There is one reason: my review last year…read moredidn't include Ian Morrison, the new Keelboat club director. It's been a terrific season at ASS. The winds have been so steady into August and the special events (blue angels, dinghy day, Monday night races) have all contributed to creating a real community there. Ian has helped take the club membership up a notch or two. As the club director he takes charge and delivers help and services for the club members and connects members together. "it's your clubhouse" he's said to me more than once. I've learned so much from him this year about rigging and racing. How I love Annapolis Sailing School. Thank you Rick Nelson for bringing Ian on board for us.

    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!

    Waypoints Annapolis - boating - Updated May 2026

    Loading...
    Loading...
    Loading...