Classic Sailing

Chicago, IL
37 ft
Boat length
Up to 6
Passengers
Captained
This boat is rented with a captain
100%
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.



Read more
Owned by
Rosalie

Amenities

Bathroom
Stereo
Stereo Aux Input
Cooler/Ice Chest
Swim Ladder
Refrigerator
Anchor

Specifications

Year
1969
Length
37 ft.
Make
Chris Craft
Model
Apache 37
Capacity
6
See all
/ (excl. fees)
Date
Duration
Start time
You won't be charged yet

Ratings & reviews

0.0
(0 rating)

Boat location

Exact location information is provided after a booking is confirmed.

Your crew

Boat owner
Rosalie
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
See profile
  • Response rate: 100%
  • Avg. response time: < 30 mins

Things to know

Allowed on boat

swimming
alcohol
kids under 12
glass bottles
shoes
red wine

  • Free cancellations until 5 days before the booking start date.
  • 50% refund for cancellations between 2-5 days before the booking start date.
  • Cancellations within 2 days of the booking start date are non-refundable.
See policy

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.

Learn more

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.