Whether you're a first-time sailboat buyer, a new boat owner, or an experienced cruiser looking to reduce maintenance costs, understanding the true workload of sailboat ownership is essential. The purchase price is just the beginning. One of the biggest hidden costs of boat ownership is the ongoing maintenance required to keep your boat safe, seaworthy, and ready for another sailing season. Haul outs should take place every year or two, and when it's time to haul your boat out of the water, every day on land can cost you money. Most boatyards charge a daily rate while your boat is on the hard, meaning poor planning, forgotten supplies, and unexpected repairs can quickly turn a routine haul-out into an expensive project. So, what actually needs to be done when a sailboat comes out of the water? And how can you prepare ahead of time to avoid wasting money? Steal our list of the 10 things we check during EVERY haul out that we use to maintain our fleet of 20+ yachts & minimize boatyard expenses: 1. Prep & Paint the Bottom 2. Replace the Zincs 3. Clean, Polish & Coat the Propeller 4. Inspect & Service the Thru-Hulls 5. Check the Cutlass Bearing 6. Inspect the Shaft Packing or Saildrive Seals 7. Service the Bow Thruster 8. Inspect the Anchor Chain & Ground Tackle 9. Inspect the Rudder & Joints 10. Drain & Dry the Rudder — The “Secret” Final Tip ⚓️ABOUT US⚓️ The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailing. Instagram: https://www.instagram.com/thesailingacademy/ Facebook: https://www.facebook.com/thesailingacademy/ TikTok: https://www.tiktok.com/@the.sailing.acade X : https://x.com/TSailingAcademy

Ever wondered how 150+ sailboats and yachts actually get into the Annapolis Sailboat Show? Come aboard as we take you behind the scenes for what most attendees never experience: the controlled chaos that is setting up for one of the biggest sailboat shows in the country. Join Captain Jeff and The Sailing Academy crew as we bring our Viko S35 sailboat up the Chesapeake Bay to the United States Sailboat Show in Annapolis, Maryland! From packing up the boat and navigating the busy Annapolis Harbor to waiting on dockmasters, maneuvering into a crowded slip, and transforming our sailboat into a show-ready exhibit, there's a LOT that happens before the first visitor ever steps aboard. And while thousands of visitors come to admire the beautiful yachts, catamarans, and sailboats on display, most never see the organized chaos it takes to get them there. In this behind-the-scenes sailing vlog, you'll see What it takes to prepare a sailboat for the Annapolis Boat Show, Our journey up the Chesapeake Bay and the unexpected challenges of arrival day. Stick around to see how our docking goes and whether we can get everything ready before the crowds arrive! Have you ever attended the Annapolis Sailboat Show? Let us know in the comments what your favorite part was, or what you've always wondered about behind the scenes! 0:00 Intro 0:43 Prepping the boat 1:59 4:30am departure off the dock 5:56 Sunrise sail 7:55 Arrival to Annapolis 11:58 Getting into our slip 15:01 Setting up the booth ⚓️ABOUT US⚓️ The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailing. Instagram: https://www.instagram.com/thesailingacademy/ Facebook: https://www.facebook.com/thesailingacademy/ TikTok: https://www.tiktok.com/@the.sailing.acade X : https://x.com/TSailingAcademy

In this episode of our 15-part Sailing Basics series, we walk you through what we teach EVERY sailor to check before casting off. This 5-Step Pre-Departure Checklist serves to build a habit that will increase your seamanship and potentially prevent catastrophic failures while out on the water. Captain Phin will show you not only what to check, but WHY you’re doing it and what can go wrong if neglected. Add the below checklist to your notes and start developing this as a habit, no matter whose boat you are stepping aboard: Pre-Departure Checklist: 1. Safety Equipment & Flotation 2. Standing & Running Rigging 3. Sail Preparation 4. Below-Deck Systems & Bilge 5. Engine & Gear Shift Function ⚓️ABOUT US⚓️ The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailing. Instagram: https://www.instagram.com/thesailingacademy/ Facebook: https://www.facebook.com/thesailingacademy/ TikTok: https://www.tiktok.com/@the.sailing.acade X : https://x.com/TSailingAcademy

A loaded sailboat line can generate enough force to seriously injure you—and one small mistake with your hands around a winch can turn dangerous fast. In Session 5 of our Sailing Basics series, we’re covering the essential techniques every sailor should know for safely handling sailboat lines, winches, clutches, cleats, halyards, and sheets. In this video you’ll learn how to properly hold and pull a loaded line, why your thumb position matters, how far to keep your hands from a winch, and why you should NEVER wrap a loaded line around your hand. We’ll also demonstrate: How to safely load and unload a sailboat winchTraditional vs. self-tailing winchesHow rope clutches work under load How to safely release a loaded clutchUsing cam cleats and block-and-tackle systems Whether you're learning to sail for the first time, building confidence for coastal cruising, or preparing for offshore sailing, safe line handling is one of the fundamental seamanship skills you'll use every time you step aboard a sailboat. This is Session 5 of our 15-part Sailing Basics series, designed to take the mystery out of sailing and give new sailors the practical skills and understanding they need to become confident on the water. Once you’ve mastered the skills here, join us for the next session in our series: Session 6: Preparing the Boat to Leave the Dock and Subscribe to The Sailing Academy to follow along. ⚓️ABOUT US⚓️ The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailing. Instagram: https://www.instagram.com/thesailingacademy/ Facebook: https://www.facebook.com/thesailingacademy/ TikTok: https://www.tiktok.com/@the.sailing.acade X : https://x.com/TSailingAcademy

What happens to all those sailboats that never leave the boatyard? Walk far enough into almost any yacht yard and you’ll eventually reach what we call “The Land of Broken Dreams”—rows of sailboats that were once somebody’s cruising dream, but haven’t touched the water in years. So how does an enthusiastic new boat owner with dreams of cruising end up here? In this video, we walk through the forgotten end of the boatyard and break down 4 reasons sailing dreams stall out. If your dream is to own a sailboat, live aboard, cruise the Chesapeake Bay, sail offshore, or eventually sail around the world, don't make your first goal the biggest one. Get the boat safe. Build your sailing skills. Cross the bay. Visit the next port. Learn to maintain what you own. Then keep going. You may never feel 100% ready—and your boat will probably never be 100% finished. The goal is to keep the dream moving. ⛵ We want to hear from you!What do you think stops more people from actually going cruising—money, lack of sailing experience, endless boat projects, or waiting for the “right” time? Tell us in the comments. Be sure to subscribe to The Sailing Academy if you want more practical sailing education, cruising advice, sailboat ownership tips, and the skills you need to turn the dream of sailing into time on the water. ⚓️ABOUT US⚓️ The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailing. Instagram: https://www.instagram.com/thesailingacademy/ Facebook: https://www.facebook.com/thesailingacademy/ TikTok: https://www.tiktok.com/@the.sailing.acade X : https://x.com/TSailingAcademy

Welcome back to Session 3 of our 15-part foundational sailing series! Have you ever wondered how a boat can sail upwind instead of just getting blown downwind? In this lesson, we reveal what actually propels a sailboat forward. In This Episode, You'll Learn: * The Push vs. Pull Principle * How Sails Generate Lift * The Role of the Keel Have you ever experienced a stalled sail or luffing while trying to sail upwind? Let us know below! ⚓️ABOUT US⚓️ The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailing. Instagram: https://www.instagram.com/thesailingacademy/ Facebook: https://www.facebook.com/thesailingacademy/ TikTok: https://www.tiktok.com/@the.sailing.acade X : https://x.com/TSailingAcademy