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Frequently Asked Questions

  • What do I need to bring?
    While one really doesn't need much for a sailing lesson, there are a few things that will make your experience safe and comfortable. Lifejackets must be worn during lessons, and are required for our guests 18 and under for charters. We also recommend bringing water shoes, sunglasses, a hat, towel, water bottle and sunscreen. Water shoes are required for all children who participate in lessons. In the Spring or Fall, a sweatshirt and/or windbreaker is a good idea; it is always cooler out on the bay than on land!
  • How are lessons scheduled?
    The best way to schedule a lesson or charter with us is through our online booking system. If you are interested in a date/time that is not listed, are interested in departing from your waterfront home, would like to use your boat for a lesson or charter, or have any other questions, please send us an email or give us a call at 631-745-8273. You can also book by calling Silly Lily Fishing Station at 631-878-0247. If the weather looks at all questionable the day before a scheduled lesson or charter, we will be in touch to cancel, reschedule, or to make a decision closer to the scheduled time.
  • I have never sailed before! Are there any requirements before I book?
    That is no problem at all! If you are interested in a Motor Boat Charter, Sunset Cruise or Sail, Swim & Beach day, we will do all of the work! If you are interested in a sailing lesson or motor boat lesson, that is exactly what we are here for! The only prerequisite is that you know how to swim. While it is extremely unlikely that anyone would end up in the water inadvertently, there is always a small chance. Lifejackets must be worn by children under 18 at all times; we have plenty available for your to borrow if needed. For kids, it is preferable that they are comfortable in and around the water. If they are not, we will be sure to take things slowly and our sailing lesson will only occur if the conditions are perfect.
  • What about weather?
    Sailing is a very weather dependent activity; it must be suitable for the student so that the sailing experience is safe, enjoyable, and provides a good learning environment. We monitor the weather closely and will always confirm that the conditions are suitable for sailing the day before a scheduled sailing lesson or bay cruise. We have an AI interfaced home weather station on Moriches Island Road that you can view here and the corresponding SailFlow station which we use to monitor wind speed and forecasts. While we do our best to monitor and predict the weather, mother nature is mother nature, and she requires us to be flexible.
  • Are you licensed and insured?
    Yes. All sailing instructors and captains are licensed by United State Coast Guard and have up to date First Aid & CPR certifications. All of the charters and sailing lessons offered by Moriches Island Sailing are insured by Markel Marine.
  • How and when are payments made?
    Payments may be made by cash, check, or Zelle at the end of each lesson. Cash is preferred. For students who are taking more than one lesson each week, payments may be made at the conclusion of the final lesson of the week.
  • How many people may participate in a sailing lesson or bay cruise?
    Our 19' Flying Scot and 24' Eastern can comfortably fit four passengers. If the group is a mix of kids and adults, or adults are willing to squeeze, we can take up to seven people total (six passengers, one instructor/captain). Due to USCG regulations, we cannot have more than six passengers under any circumstances.
  • I have more than six people in my group. Can you please make an exception?
    No. The USCG prohibits uninspected passenger vessels from carrying more than six passengers. Any small vessel that offers to take more than six passengers is likely in violation of USCG regulations and exposing themselves to large fines and penalties. If you have a party of more than six, we may be able to do two trips, or go in two groups on two boats. If you'd like to have more than six passengers on one vessel, you'll have to go to Sag Harbor or Hampton Bays. Other than fishing "party boats," there are no vessels that can legally accomoate groups larger than six in Moriches Bay.
  • I would like to buy a lesson or charter for a friend. Do you offer gift cards?
    Yes! You can request a gift card by submitting a form on our gift card page in the top menu bar. You can gift a full lesson or charter, or a dollar amount.
  • What time of the year do you sail?
    While our start and end dates vary each year, typically we sail from mid May until October. Our busiest time of year is from late June until Labor Day.
  • Will you teach me on my boat?
    Generally the answer is yes, provided that it is a boat we are familiar with and feel comfortable teaching and sailing on. Please send us an email if you would like a lesson on your boat.
  • Do I need to worry about getting seasick?
    In short, no. Seasickness typically happens on larger boats in the open ocean when a boat begins to roll in the ocean swell. While it could happen, we have never had a guest become seasick on Moriches Bay. The only reason for concern is if you are extremely sensitive to seasickness and have felt unwell on small boats in bays in the past. Even if you have felt seasick on a large boat in the ocean, it's very unlikely that you'll become seasick on Moriches Bay.
  • Do I need to sign a waiver?
    Yes, each student or passenger must submit a waiver, or have one filled out by a parent or guardian if under the age of 18. The waiver must be submitted digitally through Smartwaiver. Hard copies are not available. Please be sure that you and every other person in your group has submitted a waiver. If we do not have a waiver on file for each participant, you will need to fill one out on your phone, which will cut into our time on the water.
  • Can I arrive to the lesson early? What if I am running late?
    We will always be ready to start the lesson at least 5 minutes before the scheduled time; if you are there and ready, we are happy to begin early. Please make every effort to arrive early or on time; due to our busy schedule we are unable to adjust the end time of a lesson due to a late arrival.
  • What is your cancellation policy?
    All lessons and charters are weather dependent; if we need to cancel due to weather, or you need to cancel or reschedule and give us more than 48 hours notice, there is no charge. Cancelling or rescheduling with less than 48 hours notice will result in a $100 charge. No shows will be charged the full price of the lesson or charter.
  • Do you provide other marine services?
    Depending on your location and type of boat, we may be able to help you set up, launch, maintain and haul your boat. When our students reach the point of sailing on their own, we often help them find a boat to purchase and work with them to get it set up for smooth sailing! Please email us at if you'd like a hand with your boat.
  • Do you offer kitesurfing lessons?
    We love to kite, but we aren't quite ready to offer lessons yet. We hope to start in the summer of 2024. For now, please get in touch with our friends over at Hampton Watersports for kiting lessons. They are located in Southampton and can be reached at 631-283-9463.
  • Do you offer sailboat rentals?
    We do not rent our sailboats, but our friends at Silly Lily Fishing Station rent Sunfish and Flying Scots, the same sailboats we teach our sailing lessons on! You can book a rental from Silly Lily Fishing Station here. Silly Lily also rents small motorboats, they're a great way to get out on Moriches Bay!
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