Classic Sailing

37 ft
Boat length
Up to 6
This boat is rented with a captain
Owner’s response rate

The boat

Join R & R Classic Sailing cruising along Chicago's magnificent shoreline. Enjoy a restful and relaxing sail with Captain Rosalie and Randy on a beautifully restored 37' Cris Craft Sparkman-Stevens that raced Rhode Island to Bermuda and the Chicago Mac race. Come join us for spectacular fireworks cruises Wednesday evenings or beautiful Sunday sunset cruises. We also offer daytime sails for your enjoyment with time to anchor at Monroe Harbor for a bring your own lunch and beverages.

31st Harbor offers public paid parking and there is also parking just west of Lakeshore drive. A ride share is the most convenient way to arrive.

We are licensed to take 6 passengers and our prices include the captain and crew fees.

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Owned by


Stereo Aux Input
Cooler / Ice chest
Swim ladder


37 ft.
Chris Craft
Apache 37
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/ (excl. fees)
Start time
You won't be charged yet

Ratings & reviews

Boat location

Exact location information is provided after a booking is confirmed.

Your crew

Boat owner
I grew up sailing on a 42’ catamaran that my father built in the UK. When I was 11 we crossed the Atlantic Ocean and I took my 3 hour shift at the helm while my parents slept. We lived aboard sailing for 6 years and commercial fishing in Louisiana and Florida to fund our adventures. In 2012 I began teaching sailing in Chicago. In 2015, I did my second Atlantic crossing. Every year I also go cruising in the Caribbean and every summer I do private charters in Chicago. You are in the best hands inviting me to captain for your cruise. Captain Rosalie
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  • Response rate: 50%
  • Avg. response time: < 48 hours

Things to know

Allowed on boat

kids under 12
glass bottles
red wine

  • Free cancellations until 5 days before the booking start time.
  • 50% refund for cancellations between 3-5 days before the booking start time.
  • Cancellations within 2 days of the booking start time are non-refundable.
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This boat belongs to a Commercial Owner, an independent boat rental company. A Commercial Owner is an independent, Boatsetter-approved boat rental company who provides their own insurance to their guests.

A security deposit hold (not a charge) will be placed on your credit card 48 hours before your booking starts to cover any incidental damage that may occur during your rental. This hold is released 48 hours after the booking is complete, if no claims are made. The security deposit amount for the boat you are booking will be outlined during the check-out process.

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If requested, the owner can provide a list of available captains for bareboat charter or the renter can use their own qualified captain. If the boat is being time chartered, the owner will provide the Captain.