Top Illinois Sailing Trips

We were looking for something to do before leaving town and this popped up when I was surfing groupon. We didn't book through groupon because the conditions were really vague, went to operator website and ~$50/head for an hour boat ride seemed nice so we did it. What we booked was a 75 minute sail with city skyline viewing. When we showed up, we found people dressed and pirates and I was worried it was gonna be very kitschy and showy. As it turns out, they do embrace the pirate theme a little, but it's not in your face and over the top; it didn't turn it into a farce. Motored away from the pier and then they enlist help from the guests to unfurl the sales (under heavy supervision), they cut the motor, sail out the breakwater for a while, u-turn and come back in. We had a 50ish year old woman on the foredeck with us who was as friendly and nice as could be. We had a blast (and the weather certainly helped). I'd have liked a bit longer sail, but she commented that they used to do 90 minute jobs and people thought they were too long (can't please everybody).

Awesome experience. Very family friendly and everyone is friendly and welcoming. Would highly recommend!!

The fireworks sail was absolutely amazing! It's a great way to relax and spend time with friends. I didn't have any drinks, so I can't attest to the prices or the quality of the alcohol served. However, I know that I can't wait to do this sail again next year, perhaps when family members come in from out of town to visit. It's such a different view to watch the fireworks out in the lake. Definitely worth the money.

The captain knows exactly where to drop anchor on the lake so you are directly underneath the fireworks. We have never been so close before. It was crazy beautiful

Captain Ulysses was great. Fun, friendly, and very responsible. Good communication leading up to the trip. A beautiful way to see the Chicago skyline.

We LOVED our sailing excursion with Captain Ulysses! 6 of us went during a girls weekend, and it was the absolute highlight of our trip. Captain Mike and Captain Ulysses got us on board right on time, and we enjoyed two hours of sailing with great wind and a ton of excitement. If you’re considering booking, DO IT. As a group of moms, we tend to spend our girls trips catching up and reminiscing, and not always making NEW fun memories together. This was exactly what we needed, and we’ll remember this outing forever. We were begging to buy out the next hour, but someone already had it booked. We’d absolutely do it again! Thank you for a great time!

Great staff, very much offering the guests the ability to participate in the raising of the sails. It was very much like what the description offered. Our experience was at 7pm on Labor Day Sunday. Watching the sun set behind Chicago’s skyline and then the twinkling lights was magical. Wear rubber souled flat shoes for best stability on the ladders to the fore and aft decks. Best way to get there is via Rideshare mid-Navy Pier drop off.

Had a great time! Crew was very friendly and as a first time visitor to Chicago, it was awesome to see the city skyline from the sea.

This is a great way to see the fireworks on a tall ship very friendly staff, perfect positioning for fireworks.

A great trip aboard the tall ship Windy. The fireworks display was well worth waiting for and highly recommended! And afterwards I was one of the 4 volunteers who helped raise the mast (quite an enjoyable experience) for us to sail around before returning. The crew were very accommodating. Altogether a quite relaxing time really.

Wonderful Chicago excursion! Our guide was so personable and accommodating! Great way to see the Chicago skyline and enjoy some relaxation. Highly recommend!

My husband and I had a wonderful cruise during our trip to Chicago. Seeing the city from the water was a unique twist on the typical tours and absolutely beautiful. The sailboat was pristine and our captain was incredibly engaging, answering our endless questions both about the city’s history and sailing. This was a perfect way to spend an afternoon. I would absolutely recommend this tour!

A wonderful way to see the Windy City on a beautiful day! The tall ship was so wonderful, as was the friendly crew! Super fun activity!

Great way to spend a morning or afternoon! Super relaxing and fun. The crew was very friendly and let us raise the sails.

Great experience on a beautiful boat. The crew was amazing and very friendly. The tour length was perfect and allowed for a relaxing night and a great view of the city. Very easy to book tickets directly at Nave Pier.

We sailed on the Tall Ship Windy for a Saturday night fireworks cruise. The staff were fun and friendly. The Captain navigated through the crowded boat traffic so we had the best view of the fireworks. We had a blast!