easy
2 hours
Comfortable sitting is recommended, no physical exertion required.
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.
Pop the question, take incredible photos and celebrate in luxury!
Embark on a romantic 2-hour engagement photos or proposal cruise aboard a luxurious 37' sailboat. Experience breathtaking views of the city from the water, enjoy complimentary champagne, and create unforgettable memories with your loved one. With a USCG-certified captain and all amenities provided, this is the perfect setting for your special moment.
Our private Engagement Cruise will take you & your loved one on a favorable sail along the gorgeous Lakefront, giving a unique experience of seeing the city from the water. If you're looking for the perfect place to pop the question or take incredible photos - this is the cruise for you.
✅ USCG-Certified Captain trained in First Aid and CPR.
✅ Private use of our fully-permitted, fully-insured sailing yacht.
✅ Complimentary beverages and snacks on board.
✅ Fully stocked kitchenware, fridge and bathroom.
✅ Stereo surround sound speakers with Bluetooth connection.
❌ NO Separate captain fee
❌ NO Fuel and docking fee
❌ NO Damage/cleaning deposit
We do our best to have on board everything you might need, some personal items to keep in mind include:
You may bring any food and beverages of your choosing including beer, wine, champagne, or hard seltzers. We have alcohol for purchase on board or ahead of time and can provide catering for an added fee.
If there is current or forecasted lightning or high wind, we make a weather cancellation one hour before your scheduled departure and provide a full refund.
You can see all of our FAQs here on our website
On A Boat Sailing, LLC
info@onaboatsailing.com
312.619.7858
Reserve your spot early to ensure availability, especially for special occasions.
Plan your cruise on a clear day for the best experience and breathtaking views.
Capture the stunning skyline and your memorable moments on deck.
Get comfortable and enjoy the scenery before setting sail.
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.
Capture the stunning city views and special moments during the cruise.
Bring a jacket in case of breeze or cooler weather on deck.
any specific
Wear suitable footwear for boarding and moving around the boat.
Bring decorations or personal items to personalize your occasion.