Cancel

Open app

Search

Two Brothers Sailing Adventures

4.8 (12 reviews)
Open 8:00 am - 8:00 pm
Updated 2 months ago

Two Brothers Sailing Adventures Photos

You might also consider

More like Two Brothers Sailing Adventures

Recommended Reviews - Two Brothers Sailing Adventures

Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
Yelp app icon
Browse more easily on the app
Review Feed Illustration

Reviews With Photos

We went out with capt jeff this Monday for a wonderful cruise. The boat is awesome and jeff is an entertaining captain teaching us about sailing and letting my son take a quick swim. We brought food and couple of adult beverage and had a nice dinner and drinks. My daughter did get a little sea sick but that was the only thing that went slightly wrong. The Lake was awesome tonight with a great sunset. I would love to go again!

Sunset cruise
Tiffany K.

Great event and awesome experience! Jeff is super friendly and helpful. He left me steer for a while until I almost crashed into another boat... Oops. But really it was so relaxing!! My husband commented that he felt like all his troubles were left on land. Sunset cruises are great. He helps you customize your experience and makes it so so breezy.

See all

6 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

5 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

5 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

8 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

9 years ago

Helpful 1
Thanks 0
Love this 1
Oh no 0

9 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

7 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

7 years ago

Great time on the lake with Captain Jeff! It was the highlight of our girls weekend. Lisa B.

Helpful 0
Thanks 0
Love this 0
Oh no 0

14 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

11 years ago

Helpful 1
Thanks 0
Love this 0
Oh no 0

8 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

10 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

Ask the Community - Two Brothers Sailing Adventures

Review Highlights - Two Brothers Sailing Adventures

Jeff is great very entertaining and engaging the 2 hour tour is great and at a very reasonable price.

Mentioned in 7 reviews

Read more highlights

You might also consider

Wendella Tours & Cruises

Wendella Tours & Cruises

4.4
(1.6k reviews)

First time on the architecture boat tour on the recommendation of a bunch of friends who had…read morealready taken the tour in the past. Personally, I was pleasantly surprised. The words "architecture" and "boat tour" don't immediately spell a fun time in my mind. But this tour is 1) a pleasant way to see the center of Chicago from the water, 2) actually interestingly informational, as the tour guides are extremely on top of their game, 3) much more dense that you expect (these guys are talking non-stop), and 4) surprisingly good views, especially when you get all the way out into the edge of the harbor! Finding the place was a bit roundabout, but once we got there, staff were super friendly, and it was easy to get on the boat and off to our next stop afterwards. Parking suggestions on the site are solid too. I'm not sure whether I'd do it again, but I'd definitely recommend it as a must-do stop on any visit!

90 minute Architecture tour…read more It was a cloudy, windy, and cold day in June. Even with the clouds rolling in & out and blocking a lot of the views it was still interesting and our awesome guide, Bobby, was knowledgeable, funny, and kept it interesting and flowing for adults and kids. The tour starts on the river heading towards Lake Michigan. The ride into the lock was a little lengthy as we had to wait for them to fill it with boats first. Once we made it onto Lake Michigan it was very chilly, but I'd rather be freezing than sweating like crazy on a hot humid day. We were on a smaller boat which was nice. - upper deck: Seats long the outside and chairs in the middle. Only wish they had cushions. - lower deck: had some small seating outside and standing bar tables - lower deck: indoor restrooms and bar area - snacks, drinks available for purchase If rain is in the forecast bring paper towels to clean off your seats. I also saw some people with Wendella rain ponchos, but not sure where to get them? Really fun and beautiful way to see the city! Highly recommend!

Two Brothers Sailing Adventures - boatcharters - Updated July 2026

Loading...
Loading...
Loading...