Windjammer Excursions

Unique Multi-Day Adventures for friends and Family

A Unique Vacation

Forge unforgettable bonds with friends and family on BaySail's Appledore IV windjammer trips. Step aboard this classic tall ship and immerse yourselves in the timeless beauty of traditional sailing. Leave the distractions of daily life ashore as you hoist sails together, navigate by the stars, and feel the gentle sway of the vessel as a unified group. Our windjammer trips offer a unique opportunity to reconnect with loved ones and nature, learning the art of sailing from our experienced crew. Whether your group includes seasoned sailors or first-time adventurers, you'll find a strong sense of camaraderie and shared experience on board.

These windjammer trips are more than just a vacation; they're an immersive experience into the world of traditional sailing, designed for creating lasting memories with those closest to you. Enjoy delicious meals prepared onboard, relax on deck with shared stories, or simply gaze at the breathtaking sunsets over the water as a family or group of friends. Each voyage is a chance to explore new destinations, discover hidden coves, and strengthen the ties that bind you. Join us for an unforgettable journey where the rhythm of the sails and the tranquility of the open water will rejuvenate your spirits and create shared experiences that will last a lifetime.

Sailing ship on calm water during sunset with colorful sky.

Imagine the Appledore IV as your personal sailing haven. Our windjammer trips offer customizable experiences, allowing you to tailor your voyage to your group's preferences. Whether you're planning a family reunion, a friends' getaway, or a unique corporate retreat, we can work with you to create an itinerary that suits your needs. From choosing specific anchorages to arranging special onboard activities, we aim to make your journey truly your own. The Appledore IV provides a private, intimate setting, perfect for fostering connection and creating shared memories away from the crowds.

If you're ready to embark on a one-of-a-kind sailing adventure, reach out to us below. We're happy to discuss your vision and answer any questions you may have. Let us help you plan a personalized windjammer experience that will exceed your expectations and leave you with unforgettable moments on the beautiful waters of Lake Michigan.

Customized and Private

Sailboat with passengers sailing under a suspension bridge on a sunny day.

2025 Applications are OPEN

Interested in signing up your student for our 2025 Windward Bound Trips?