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Writer's pictureJonathan Puleio

Top 10 Reasons to Charter a Sailboat this Summer

Updated: Jun 12



Private Sailing Charter in Oyster Bay, NY
S/V WINDSWEPT | Oyster Bay, NY

Thinking about chartering a sailboat this summer? Read below to learn more about what makes private sailing charters so compelling!


  1. Choose your own adventure! Sail when you want, where you want and with who you want! Whether you are celebrating a special occasion, learning to sail, or entertaining clients, you are in complete control of your experience from start to finish!

  2. Learn to sail! When you book a private charter or sailing lesson, you can choose how involved you want to be in sailing the boat. Hoist and trim the sails, adjust the control lines, and take the helm while tacking and jibing if you so choose!

  3. Stress free boating! It's no secret that owning a boat can be a headache. Repairs and maintenance are costly and require time and knowledge of multiple, complex systems. When you charter a sailboat, you simply step aboard and cast off! The burdens of yacht ownership are non-existent.

  4. Knowledgeable Captains! The U.S. Coast Guard closely regulates the charter boat industry. Captains must pass rigorous written exams and provide evidence of at least 360 days of sea time to become licensed. Charter boat captains must also pass a medical exam, a CPR/first aid course, and belong to a drug testing consortium. When you book a USCG captained private sailing charter, rest assured, you are in good hands!

  5. Connect with nature! Nothing beats spending a day on the water surrounded by nature. You are likely to see schools of jumping fish, scores of migratory birds, and maybe even a few sea turtles bobbing on the surface! Sailing is an immersive experience that allows you to reconnect with all of nature's elements.

  6. Create long lasting memories with loved ones! Private sailing charters are perfect outdoor activities for creating memories with families, friends, and couples. Beautiful photos opportunities await!

  7. Entertain your clients! If you are looking for an alternative to golf outings, dinners, and happy hours, a private sailing charter might just be the ticket! Work with your charter boat captain to create a memorable experience that will help you develop long-lasting client relationships!

  8. Reward and challenge your team! Private sailing charters make wonderful team building exercises because sailing requires teamwork and collaboration. Your team will develop new skills and have some fun along the way!

  9. Beat the heat and go for a swim! Few things are more refreshing than jumping off a boat on a hot summer day after a relaxing sail. Sailboats like WINDSWEPT are equipped with walk through transoms and integrated swim platforms that make getting on and off the boat a lot easier.

  10. Relax and decompress! An escape from your daily routine is healthy, even if just for a few hours! Sailing charters offer guests a unique opportunity to temporarily unplug and disconnect from their hectic lives. You are likely find the experience rejuvenating on multiple levels!

While there are quite a few more to list, these are my top 10 reasons to charter a sailboat this Summer!

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