Embarking on Season Three with SailTime Chicago

The mainsail hoisted high on the mast of a sailboat

Kent and I are excited to return for our third sailing season with SailTime Chicago aboard Red Sky, our Jeanneau Sun Odyssey 349. We've enjoyed memorable moments, from hosting family during events like the Chicago Air and Water Show to crossing Lake Michigan. We're eager for more adventures and updates in 2025!

Our Grand Traverse Bay Adventure

This blog is about sailing.

Just six months after completing sailing school, we took the plunge and chartered our first sailboat in beautiful Grand Traverse Bay, Michigan. This maiden voyage - our first time without an instructor - was a true test of our skills and a fantastic adventure filled with challenges and triumphs. It solidified our love for sailing and taught us valuable lessons about teamwork, living in the moment, and the magic of the Great Lakes.

A Debrief on Our BVI Adventure

A dramatic sunset as seen from the deck of a catamaran

Our first-ever sail in the British Virgin Islands exceeded our expectations. Sharing the stunning natural beauty with my sister and niece, the thrill of navigating the open waters, and the unexpected encounters with fellow travelers made for unforgettable memories.

Top Priorities for a Successful BVI Sailing Trip

an AI rendering of a catamaran at a dock, with people standing on the deck and the sun shining in the background

Kent details the planning of our weeklong sailing trip to the British Virgin Islands, where we have chartered a Fountaine Pajot 40 Lucia catamaran named Vahevala. Arriving in Tortola, we will prioritize safety, comfort, and fun while deciding on our sailing route. We'd love to visit Anegada, but will have to take into consideration the wind conditions and our guests' comfort level. A flexible itinerary is necessary for optimal experiences.

Crossing Lake Michigan – an Epic Adventure: The Whole Story

The Chicago skyline seen from Lake Michigan in the background, with a sailboat in the foreground

The journey across Lake Michigan, from Chicago to New Buffalo and back, was a beautiful and eventful adventure. But a whole lot happened! The trip involved sailing, motoring, a famous freighter ship, and unexpectedly running aground with family on board! However, through the kindness of strangers and maritime miracles, we overcame the challenges. The joy of reaching the finish line after the long passage was totally worth it!