Adventure Collective
Water-Activities: Proposals & Engagements Cruise by The Adventure Collective - City of the location

Water-Activities: Proposals & Engagements Cruise by The Adventure Collective

Chicagoeasy

Difficulty

easy

Duration

2 hours

Fitness Level

Comfortable sitting is recommended, no physical exertion required.

Overview

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.

Chicago, Illinois

Proposals & Engagements Cruise

Pop the question, take incredible photos and celebrate in luxury!

Select participants and date

About This Adventure

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.


2-hour Engagement Photos or Proposal Cruise

37' Luxury Sailboat

USCG-Certified Captain

🎡 Departing from the all-new Navy Pier Marina

🥂 Complimentary Champagne Toast


What you'll do

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.

What's Included

✅ 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

FAQ

🎒 What should I wear or pack?

We do our best to have on board everything you might need, some personal items to keep in mind include:

  • Rain jacket or layers for cooler days
  • Boat shoes, sandals, or non-black soled tennis shoes

🍾 What food and drink can I bring on the boat?

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.

⚡ What if there is bad weather?

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.

❓ Where is your full list of FAQs?

You can see all of our FAQs here on our website


logo On A Boat Sailing, LLC info@onaboatsailing.com 312.619.7858

Adventure Tips

Book in advance

Reserve your spot early to ensure availability, especially for special occasions.

Check weather forecast

Plan your cruise on a clear day for the best experience and breathtaking views.

Bring a camera

Capture the stunning skyline and your memorable moments on deck.

Arrive early

Get comfortable and enjoy the scenery before setting sail.

Local Insights

Wildlife

  • Seagulls
  • Dolphins (seasonal)

History

This cruising area has been a hub for maritime trade dating back to the 1800s, with a rich history of sailing and exploration.

Conservation

The Adventure Collective emphasizes eco-friendly practices, including waste reduction and respecting local marine life during trips.

Select participants and date

Adventure Hotspots in City of the location

Frequently Asked Questions

Recommended Gear

Smartphone or Camera

Essential

Capture the stunning city views and special moments during the cruise.

Light Jacket

Bring a jacket in case of breeze or cooler weather on deck.

any specific

Comfortable shoes

Wear suitable footwear for boarding and moving around the boat.

Celebration items (optional)

Bring decorations or personal items to personalize your occasion.