Yahoo
6 year old master!
Great view from Port Side!
Spectacular!
Family bonding!
Now that's sailing!
WOOF!
Just chillin' with Woody!
Picture perfect!
Thumbs up from the Captain!
First Mate Woody says,
The Salty Dog Sailing Co. Boat Tours

Website: saltydogchicago.com

Phone: (312) 878-7901

Cross Streets: Near the intersection of S Lake Shore Dr and E Waldron Dr

Opening soon · 9 AM

  • Sat 9:00 AM - 10:00 PM

1559 S Lake Shore Dr, Dock N, Burnham Harbor Chicago, IL 60605-2816 ·508.43 mi

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Amenities

  • Family friendly
5.0
48 reviews
5 star
47 4 star
0 3 star
1 2 star
0 1 star
0
Tripadvisor traveler Gerakamb 09/08/25

Captain Kirk Kessler, a United States Coast Guard - Certified Master Captain, goes all out to give his passengers a wonderful experience. His boat, the Peony, is equipped in a manner to meet the needs of his guests. His first mate, Woody, a chipper mini Golden Doodle, adds a fun touch to each outing. Kirk is extremely professional, going over his shipboard rules with all his charges before they embark. His rule #1 - Stay on the boat!Captain Kirk gets a sense of each of his sets of guests, and how comfortable (or apprehensive) they are on the water. Passengers preferring a sedate, gentle excursion will get one (to the extent weather and lake conditions permit); those guests up for a more adventurous outing with 15-30 degrees of heeling will have their wishes fulfilled. As a USCG-certified Master Captain, Kirk knows what he needs to do to trim the sails and change his headings to make his cruises pleasant ones for his passengers and their predilections. A charming host/skipper, Captain Kirk will make your sail/cruise an unforgettable one - withe the beautiful Chicago skyline as your sunset backdrop. You can't do better than Salty Dog Sailing Co.!

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Tripadvisor traveler JohnDoe88 09/06/25

Captain Kirk Kessler, a United States Coast Guard - CertifedMaster Captain, goes all out to give his passengers a wonderful experience. H8s boat the Peony, is equipped in a manner to meet the needs of his guests. His first mate, Woody, a chipper mini Golden Doodle, adds a fun touch to each outing. Kirk is extremely professional, going over his shipboard rules with all his charges before they embark. His rule #1 - Stay on the boat!Captain Kirk gets a sense of each of his sets of guests and how comfortable they are on the water. Passengers preferring a sedate, gentle excursion will get one (to the extent weather and lake conditions permit); those guests up for a more adventurous outing with 15-30 degrees of heeling will have their wishes fulfilled. As a USCG-certified Master Captain, knows what he needs to do to trim the sails and change his headings to make his cruises pleasant ones for his passengers A charming host/skipper, Captain Kirk will make your sail/cruise an unforgettable one - withe the beautiful Chicago skyline as your sunset backdrop. You can't do better than Salty Dog Sailing Co.

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Tripadvisor traveler Kirk L 07/13/25

Well worth the money to get out and enjoy Lake Michigan and city skyline views. Captain Kirk and Woody we’re great hosts, and made it a great experience for us

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Tripadvisor traveler W331XEseang 05/28/24

My wife and I went on a sunset sail with the Salty Dog and loved every aspect. Would defintely recommend and plan to do this sail again on our next visit.

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Tripadvisor traveler Chuck C 09/07/23

Captain Kirk and the Peterson 34 was a great experience. We had the perfect sail. High winds and good waves brought great speed.

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