Lakeshore Sail Charters

Central Chicago

Give as a Gift
Limited quantity available
Over 280 bought

In a Nutshell

  • Many sailing times
  • Upgrade for fireworks shows
  • Experienced crew

The Fine Print

Promotional value expires Sep 1, 2011. Amount paid never expires. Limit 1/person, may buy 2 additional as gifts. Limit 6 people per boat. Reservation req'd 10 days in advance; subject to availability. Not valid until 5/1. Not valid on 8/20-8/21. Must be 12 years or older. Must sign waiver, if under 18 guardian must sign waiver. May be subject to weather. May apply value towards upgrade. Not for resale. 9% tax not included. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

A sea voyage is like a trackless train ride across the water fields, relying only on the principles of physics and magic to keep your vessel floating above the water on a thin cushion of air. Unfurl your sea wings with today’s Groupon: for $199, you get 2.5 hours of shared sailing for two people on Pianissimo from Lakeshore Sail Charters (up to a $487.50 value).

Lakeshore Sail Charters guides seafarers on a serene, luxurious cruise around Lake Michigan, enticing passengers to relax on board one of the three ships in its fleet—including Pianissimo, a 2011 Beneteau Oceanis 50. On each voyage, aqua-adventurers are guided by the steady, calloused hands and windblown visages of U.S. Coast Guard–licensed Captain Bruce Randall and the ship’s doctor, Karen Randall. At the whim of the wind's desire, no two tours on Pianissimo are alike. In between basking in the picturesque skyline views, passengers can peruse Pianissimo's amenities, including a radio, a CD player for playing Arnold Schwarzenegger Making Ocean Sounds, and a microwave.

Sailing times are at 5 p.m. and 8 p.m. Mondays–Fridays and 8 a.m. and 11 a.m. Saturdays and Sundays. The Wednesday 8 p.m. sail requires an additional fee of $30 per person.

Tall Ship Windy

The massive schooner gently bobs in the Lake Michigan waters as the Chicago skyline towers on the shore. Onboard, hardy sailors relate tales of piracy as they train their passengers to tie knots and unfurl sails. Period lessons abound onboard Windy, the lone vessel helmed by US Coast Guard-certified captains and crews. The nostalgic steed is used to educate visitors on the lake's maritime traditions and explore coastal waters. Windy also plays host to themed adventures that include fireworks shows, pirates explaining city architecture, and pirates complaining about the popularity of pool noodles. Crews strive to make each tour unique, with sailors who expound on their skills as well as performers and educators versed in history, maritime lore, art, and theater.

Customer Reviews

Perfect experience for a group of friends!
Bonnie K. · December 23, 2016
It was a great trip.
Chris H. · November 2, 2016
Had an awesome time on this ship ride. Staff were friendly and funny. Ship was just gorgeous! I would highly recommend this! Loved it!
Sandra M. · November 2, 2016
Merchant Location Map
  1. 1

    Central Chicago

    1410 Museum Campus Dr.

    Chicago, Illinois 60605

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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.
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