THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Celebrate love or a special moment with a luxurious water cruise. Find out why The Adventure Collective’s romantic sail is a must-do in the area.
Celebrate love or a special moment with a luxurious water cruise. Find out why The Adventure Collective’s romantic sail is a must-do in the area.
Book with On A Boat Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by On A Boat Sailing · Chicago, Illinois
Set sail on a romantic journey with The Adventure Collective's Proposals & Engagements Cruise, a premier water-activity experience designed for unforgettable moments. Departing from a scenic marina, this 2-hour cruise offers a perfect backdrop for popping the question or celebrating a special occasion. The vessel, a luxurious 37-foot sailboat, provides an intimate environment to share cherished memories amid stunning views of the city skyline and waterfront. With a USCG-certified captain at the helm, guests can relax knowing safety and comfort are prioritized along with celebration. The cruise boasts amenities like complimentary champagne, making it ideal for couples seeking a unique, picture-perfect setting. What makes this experience stand out in the area is the combination of a scenic waterway and personalized service, transforming a typical outing into a cinematic moment. The boat’s sleek design and peaceful waters make it an exclusive locale for proposals, anniversaries, or simply a romantic escape. This cruise not only provides breathtaking vistas but also allows guests to witness the city from a different perspective, making it a memorable highlight of their visit. Whether celebrating a milestone or just seeking an inspiring adventure, this cruise offers a blend of luxury, natural beauty, and intimacy that’s hard to match. The area’s vibrant waterfront and the professionalism of The Adventure Collective ensure every detail is handled with care. Perfect for couples wanting lush views and privacy, or groups looking to enjoy a special occasion on the water, this cruise elevates outdoor adventure travel. Visitors will leave with stunning photos and beautiful memories, forever tied to a moment shared on the water’s gentle sway.
easy.
2 hours.
Comfortable sitting is recommended, no physical exertion required.
Yes, it is perfect for couples, families, and groups of all ages.
The cruise includes champagne, boat ride, and all necessary safety equipment.
Yes, special requests like flowers or music can often be accommodated with prior notice.
Yes, cruises are subject to weather conditions; rescheduling may be necessary in case of poor weather.
Guests can request special beverages or snacks in advance.
Arrive at least 15 minutes before departure to settle in and prepare for boarding.
This cruising area has been a hub for maritime trade dating back to the 1800s, with a rich history of sailing and exploration.
The Adventure Collective emphasizes eco-friendly practices, including waste reduction and respecting local marine life during trips.
On A Boat Sailing is a Chicago-based private charter company offering curated sailing and yachting experiences on Lake Michigan. The company specializes in a range of private cruises including skyline sunset sails, lakefront sightseeing, swim-and-sail playpen outings, wedding and wedding-party charters, engagement and proposal cruises, Navy Pier fireworks cruises, and group yachting aboard larger vessels. Trips operate aboard a fleet that includes a 37' sailboat, the S/V Dragonfly, and the larger Yacht Guppy for big groups. Each charter includes a USCG-certified captain responsible for navigation, safety briefings, and a professionally managed experience. Add-on services include premium drink packages with pre-ordered wine, champagne, beer, and seltzer, and guests are welcome to bring BYOB snacks and beverages on most cruises. Bookings are designed for private groups seeking a tailored event on the water, from romantic two-hour engagements to four-hour celebration charters and three-hour fireworks cruises. On A Boat Sailing highlights clear departure logistics from Chicago waterfront locations and offers complimentary light snacks and select beverages on several trips. Safety and comfort are emphasized through certified captains, fully equipped yachts, and adherence to local maritime regulations. The business is positioned for authentic Lake Michigan experiences, delivering skyline views, swimming stops, and customizable itineraries for family gatherings, corporate outings, and special events. On A Boat Sailing provides transparent trip summaries, duration options, and vessel details so prospective guests can choose the best private charter for their occasion. Seasonal options.
Book with On A Boat Sailing