Two Brothers Sailing Adventures Chicago

Two Brothers Sailing Adventures Chicago

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Regal Coach Lines
Regal Coach Lines
1111 W. 48th Street

08/03/2025

Red Sky in the morning is a sailors warning

Photos from Two Brothers Sailing Adventures Chicago's post 06/05/2025

Beautifull double Rainbow at the beer can races last night

Photos from Two Brothers Sailing Adventures Chicago's post 06/03/2025

Congratulations to our team Vagabond sailing
We completed our first regatta. the Chicago Columbia yacht club colors regatta
And just special thanks to twobrothersailingchicago for making it happen

Photos from Two Brothers Sailing Adventures Chicago's post 07/29/2024

Come sailing on Vagabond

Photos from Two Brothers Sailing Adventures Chicago's post 06/04/2023

Having fun out on Lake Michigan Beautiful day

Photos from Two Brothers Sailing Adventures Chicago's post 11/30/2021

Two Brothers Sailing Goes to the Caribbean! British Virgin Islands Here We Come!!
January 8-15 and 15-22. Two different weeks to choose from. Ask about other dates.
Couples and singles welcome. 7 nights of beautiful star-filled skies and 8 days of some of the best sailing in the world. Come, swim, snorkel, dive, sail, fish, dance eat drink and be merry!
Passengers: Up to 6 each boat; 2 per cabin
The Boat:
Until we receive deposits, we can’t confirm an exact boat but there are many and they are all well-appointed. For sure the boat will have 3 cabins, 2 heads, 41’-45’ monohull. The boat will carry full liability and damage insurance. You’re in good hands, this will be Capt Jeff’s 3rd BVI trip! You will be asked to sign the typical waiver of release of liability for the Captain.
Captain: Jeff Harris, 100 Ton Master USCG Captain’s License; US Sailing Instructor. phone 630-816-1427 for info
You will be asked to pitch in to help sail the boat…but trust us, it’s so much fun and very easy!!
Base Cost: Double Occupancy Cabins: $1,500 per person

11/18/2021

Two brother Sailing at the Bluemoon Sailing Club are having an end-of-the-year party at the Chicago Corinthian yacht club in Montrose Harbor this Friday from six till whenever come on down if you feel like it

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Chicago, IL