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FRIDAY'S • SUNDAY'S 6:30PM

Skyline Sunset Cruise

2-1/2 Hour Private Charter

 Up to 7 Guests

Money Back Guarantee

Relax & enjoy a captained sunset cruise aboard our 37' luxury sailing yacht, Dragonfly.

Bring your own snacks & drinks, play your own music, and take in the views of our city's iconic skyline at dusk. 

500+ 5-star reviews
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Luxury sailing meets summer sundowners for you & your crew.

Explore your 37' luxury sailing yacht for the evening, S/V Dragonfly.

Guests:

Up to 7

Length:

37'

Bluetooth

Speakers

Private
Bathroom

Refrigerator
Access

Kitchenware
Available

S/V Dragonfly offers world-class sailing with comfortable amenities, encouraging you & your guests to focus on the adventurous day ahead.

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The bimini umbrella in the cockpit gives ample shade and some light rain protection in our main seating area. Willing guests are welcome to relieve our captain and try their hand at the helm!

Lounging space for sunbathing and lake-gazing is available on the foredeck. This will be a popular locale for photo opportunities on beautiful days! Those camera rolls are no match for these views.

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Down below, the teak interior cabin has two private changing rooms, a bathroom with shower, kitchen and comfortable salon seating area. The perfect place to store your bags, keep your drinks cool and prepare the days provisions.

500+ FIVE STAR REVIEWS

7 years of fresh waters, exclusive parties & unforgettable experiences.

Our private Skyline Sunset Cruise will take you & your guests on a favorable sail along the gorgeous Lakefront, giving a unique experience of seeing the city from the water at sunset. If you're looking for the perfect happy hour in Chicago - this is the cruise for you.

Starting at $999 for up to 7 guest

FRIDAY • SUNDAY
DEPARTING 6:30PM

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Golden Sail Money-Back Guarantee

Bad weather? Unexpected issues? We recognize things come up. Our money-back guarantee ensures you have the freedom to make adjustments with ease, providing peace of mind in the weeks and days leading up to your planned outing with us.

100% Refund up to Two Weeks From Departure

50% Refund up to 48 Hours From Departure

Full Refund for Weather Related Cancellations

Swap Dates With No Fees
Subject to Availability

Three easy steps to pre-book your private boat cruise this summer:

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STEP 1 - Choose Your Adventure
Browse our all charters & cruises page. We offer something for everyone!

STEP 2 - Recruit Your Crew
Fire up those group chats and start recruiting. S
ummer weekends will sell out.

STEP 3 - Lock-In Your Big Day
Book with a 50% fully-refundable deposit. Remaining balance to be paid at end of experience.

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Skyline Sunset Cruises are limited.
Don't get left in the wake - Book now!

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