THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Elevate your boat trip with pre-ordered premium drinks, making every sail more luxurious. Discover how On A Boat Sailing adds convenience and class to your water adventure.
Elevate your boat trip with pre-ordered premium drinks, making every sail more luxurious. Discover how On A Boat Sailing adds convenience and class to your water adventure.
Book with On A Boat Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by On A Boat Sailing · Chicago, Illinois
Sailing through pristine waters offers not just breathtaking views but also a chance to elevate your boat day with premium drink packages. At On A Boat Sailing, located in the heart of a vibrant marine area, guests can indulge in a curated selection of beverages that turn a casual cruise into a celebrated event. Imagine relaxing on deck, seas shimmering beneath you, with chilled wine, bubbly champagne, crisp beer, and refreshing seltzers pre-ordered to make your outing seamless and fun. This service stands out for its convenience, saving you time and effort while ensuring your favorite drinks are on ice and ready when you are. The company’s location in a popular boating hub makes it an ideal addition for day trips, sunset cruises, or extended sailing adventures. The natural beauty of the surrounding waters—featuring crystal-clear coves and dynamic marine life—complements the luxurious experience of sipping a cold drink while drifting past scenic islands or rugged coastlines. The accessibility of curated drinks means even those new to boating can enjoy a sophisticated outing without the hassle of bringing their own beverages or going ashore for supplies. Whether celebrating a special occasion or simply unwinding with friends, On A Boat Sailing's premium drink packages provide a memorable way to enhance your maritime journey. Their focus on quality, convenience, and customer experience makes this offering a standout in the local sailing scene. This approach transforms a standard boat trip into a polished, enjoyable event, reinforcing why this company is a favorite among locals and visitors alike seeking effortless luxury on the water.
easy.
1–4 hours.
No physical fitness required; suitable for all ages
Yes, but pre-ordering from On A Boat Sailing ensures your drinks are chilled and ready for your trip.
Group sizes vary; contact the company for specific arrangements and custom packages.
Absolutely, a variety of non-alcoholic beverages are included in the packages.
While primarily alcohol-focused, special requests can be accommodated if noted in advance.
No, the packages include everything you need for a comfortable experience.
Trips may be rescheduled or canceled due to unsafe weather conditions, with assistance provided for rescheduling.
This region has a rich maritime history dating back over a century, with numerous local legends tied to its waters.
The company practices eco-friendly boating and supports local marine conservation efforts to preserve the area's natural beauty.
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