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Two-Hour BYOB Private Sailing Cruise for Two or Six from Offshore Adventures Chicago (Up to 70% Off)

Offshore Adventures Chicago - Monroe Harbor

88% of 265 customers recommend

Give as a Gift
Over 640 bought
Limited quantity available

In a Nutshell

Daytime or sunset Lake Michigan cruises delight with views of the Chicago skyline; passengers can bring along their own drinks and playlists

The Fine Print

Promotional value expires Jun 15, 2014. Amount paid never expires. Limit 3 per person, may buy 3 additional as gifts. Valid only for option purchased. Online reservation required at least 7 days in advance. 24hr cancellation notice required. Must sign waiver. Limit 6 people per boat. Not valid on fireworks cruises. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.


Sailors learn to be experts at knot tying, from securing the vessel with a tight anchor hitch to securing the captain after he succumbs to madness and tries to eat his own hook hand. This Groupon is a mutinous bounty.

Choose Between Two Options

  • $69 for a semi-private two-hour BYOB sailing cruise for two (up to a $220 value)
  • $199 for a private two-hour BYOB sailing cruise for six (up to a $660 value)

Cruises accomodate up to six people. The semi-private tour will be paired with up to four additional passengers.

Guests embark on a choice of the skyline or the sunset cruise. The skyline cruise runs Monday–Friday at 3:30 p.m. and Saturday and Sunday at 11 a.m., 1:30 p.m., and 4 p.m. The Sunset cruise runs seven days a week at 6:30 p.m. Both cruises follow a choice of three routes, all of which showcase Lake Michigan’s views of the Chicago skyline. Flatware, cups, and napkins are provided, as well as a cooler for beverages brought on board; passengers can also play their own music. For more information, see the FAQ page.

Offshore Adventures Chicago

The 35-foot Alpha Puppy and the 30-foot Sundog could be the names of two extremely long dachshunds, but they're actually the two boats comprising Offshore Adventures Chicago's fleet. Captain Rick, a USCG Master Captain, helms the boats on the company's Lake Michigan cruises, with routes that highlight views of the city's skyline. As he steers, passengers enjoy beverages they brought along and listen to their personal playlists rather than the music of a nearby seagull pecking its xylophone. During the summer, twice-weekly night cruises augment the typical cruise selections and offer spectacular views of the city's fireworks displays.


88% of 265 customers recommend

  • “We had a great time and will go sailing again. I highly recommend the experience!”

  • “Great experience, the captain was knowledgeable and friendly! We had a lovely time.”

  • “Just be sure to read the fine print always to be sure of what you're buying/getting.”

  1. A

    Monroe Harbor

    400 E Monroe St.

    Chicago, IL 60603


    Get Directions

Bring along your own bottle of wine or beer to enjoy
Outdoor activities, from cycling to sailing
15% Bonus Savings
Get an extra 15% off local restaurants, spas, salons, and more to use within 48 hours of your Goods order! See details
By purchasing this deal you'll unlock points which can be spent on discounts and rewards. Every 5,000 points can be redeemed for $5 Off your next purchase.