THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Set sail from Traverse City with Wind Sailing’s private cruises that balance serene lake views and intimate experiences. From daytime sails to sunset cruises and special event air show trips, discover a fresh way to experience Lake Michigan’s Grand Traverse Bay.
Set sail from Traverse City with Wind Sailing’s private cruises that balance serene lake views and intimate experiences. From daytime sails to sunset cruises and special event air show trips, discover a fresh way to experience Lake Michigan’s Grand Traverse Bay.
Situated on the pristine shores of Lake Michigan’s Grand Traverse Bay, Traverse City offers more than just picturesque vineyards and cherry orchards—it invites travelers onto the water for unforgettable sailing experiences. Wind Sailing, a family-owned charter service, provides private cruises and sails that stand out as some of the most inviting ways to connect with Northern Michigan’s unique aquatic landscape.
Wind Sailing’s fleet centers around the beautifully maintained ’Second Wind,’ a graceful sailboat helmed by Captain Loren, whose warmth and expertise come highly praised. Whether you book a five-hour private Power Island Cruise or a two-hour sunset sail, every trip promises a tranquil escape and distinctive lake vistas. Power Island itself, located off the coast, offers a quiet backdrop of untouched shoreline, old-growth trees, and crystal-clear waters, making it a compelling destination for boaters.
Verified experiences and guided adventures in the surrounding area.
Operated by Wind Sailing · Traverse City, Michigan
The company’s private sunset sails are especially popular; as the sun dips below the horizon, passengers can savor panoramic views from the bow alongside carefully selected beverages, creating a perfect blend of romance and relaxation. For families, Wind Sailing balances hands-on fun with serene stretches—kids get to steer while parents unwind with a glass of wine. Special event cruises, such as the 2025 Cherry Festival Air Show Cruise, provide a front-row seat to aerial displays above the shimmering bay.
Traverse City’s blend of freshwater coastlines and vibrant seasons shapes the sailing experience. Spring blooms give way to warm summer breezes, while crisp fall evenings and quiet winter months present a chance to see the lake’s shifting moods. Wind Sailing’s intimate scale and local knowledge bring a personal touch missing from larger, commercial tours. Their commitment to a relaxed pace and guest-led adventure makes Wind Sailing a must for those seeking a distinctly Northern Michigan sailing outing beyond the usual tourist circuit.
Yes, children are welcome aboard, and Captain Loren often includes them by letting them steer the boat under supervision.
Some trips include light snacks and drinks selected by the crew; guests can also bring their own refreshments.
The Second Wind comfortably fits small groups, making it ideal for private charters with family or friends.
No sailing skills are required; the captain handles all navigation, though guests may steer if desired.
Yes, Wind Sailing schedules unique event cruises such as the Cherry Festival Air Show Cruise, but availability varies each year.
Safety is the top priority; Wind Sailing monitors conditions closely and may reschedule or cancel trips if necessary.
Wind Sailing is a charter company based on West Grand Traverse Bay that specializes in private sailing and cruising experiences for families, groups, and visiting guests. The company operates a range of curated trips including a high-adrenaline Cherry Festival Air Show Cruise, two-hour private day sails, two-hour private sunset sails with regional wine and light snacks, and a five-hour Power Island cruise with swimming, rock hunting, and water toys. All experiences are private by design, allowing guests to bring beverages and lunch on select trips while enjoying attentive, professional crew service. Safety, local knowledge, and guest comfort are prioritized through well-maintained vessels, thorough pre-departure briefings, and experienced captains familiar with bay conditions and scenic highlights. Wind Sailing frequently adapts itineraries to weather and guest preferences, offering flexible start times and personalized guidance for first-time sailors who want to take the helm. The Power Island cruise includes a full galley and provisions for a comfortable day afloat; sunsets emphasize relaxation with regional white wine and light snacks. For airshow events, Wind Sailing positions guests directly under aerial routes to maximize viewing while maintaining maritime safety. Booking is handled via The Adventure Collective listings with clear pricing and private-group options; deposits and cancellation policies are transparently communicated before confirmation. Wind Sailing’s combination of private charters, curated itineraries, and attention to safety and hospitality makes it a reliable choice for memorable Bay experiences, from quiet sails to action-packed airshow cruises. Customer reviews highlight professionalism, clear communication, and unforgettable on-water memories for groups and families.
Situated on the pristine shores of Lake Michigan’s Grand Traverse Bay, Traverse City offers more than just picturesque vineyards and cherry orchards—it invites travelers onto the water for unforgettable sailing experiences. Wind Sailing, a family-owned charter service, provides private cruises and sails that stand out as some of the most inviting ways to connect with Northern Michigan’s unique aquatic landscape.
Wind Sailing’s fleet centers around the beautifully maintained ’Second Wind,’ a graceful sailboat helmed by Captain Loren, whose warmth and expertise come highly praised. Whether you book a five-hour private Power Island Cruise or a two-hour sunset sail, every trip promises a tranquil escape and distinctive lake vistas. Power Island itself, located off the coast, offers a quiet backdrop of untouched shoreline, old-growth trees, and crystal-clear waters, making it a compelling destination for boaters.
The company’s private sunset sails are especially popular; as the sun dips below the horizon, passengers can savor panoramic views from the bow alongside carefully selected beverages, creating a perfect blend of romance and relaxation. For families, Wind Sailing balances hands-on fun with serene stretches—kids get to steer while parents unwind with a glass of wine. Special event cruises, such as the 2025 Cherry Festival Air Show Cruise, provide a front-row seat to aerial displays above the shimmering bay.
Traverse City’s blend of freshwater coastlines and vibrant seasons shapes the sailing experience. Spring blooms give way to warm summer breezes, while crisp fall evenings and quiet winter months present a chance to see the lake’s shifting moods. Wind Sailing’s intimate scale and local knowledge bring a personal touch missing from larger, commercial tours. Their commitment to a relaxed pace and guest-led adventure makes Wind Sailing a must for those seeking a distinctly Northern Michigan sailing outing beyond the usual tourist circuit.
