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

Monroe Harbor

88% of 224 Groupon Customers Recommend

Give as a Gift
Over 650 bought
Limited quantity available

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.


It was a great way to celebrate a birthday and enjoy living on the lake!

Brad J., Yelp, 11/12/12

The views of the city at sunset were AMAZING and our group was able to enjoy the snacks and drinks we brought as we wished.

Chris C., Yelp, 10/3/12

Tips from Groupon Customers

  • “Make sure you follow their tips to arrive early :-)”

  • “Bill was an amazing captain, very enthusiastic and informative, the ride was fantastic!”

  • “This was a great outing! Reservations were easy, they gave good directions on how to get there (which is a bit tricky), and the ship itself was great. The captain...”

    “This was a great outing! Reservations were easy, they gave good directions on how to get there (which is a bit tricky), and the ship itself was great. The captain was friendly and great at his job, and made sure that we had a wonderful time. ”

  1. A

    Monroe Harbor

    400 E Monroe St.

    Chicago, Illinois 60603


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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

Expires Jun 15th, 2014. 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.

Outdoor activities, from cycling to sailing
Bring along your own bottle of wine or beer to enjoy