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All listings in Lake Michigan

Incredible sailboat rentals in Lake Michigan, United States.

Page 2 of 225 listings

Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
Sailing in Chicago · 6 guests

Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

5.0
Snoozed - Active 14 Jun 2027

Sailing Reviews in Lake Michigan

  1. TF

    Todd

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    This is the boat to book for a sweet sailing experience in Chicago. Super family friendly. Ocean-worthy vessel and Capt Bob and Gabby have been all over the hemisphere with it. They're more than willing to share as much knowledge as you'd like to know. I even pulled up the main sail! Bob and Gabby were great with our young children. Just wonderful people. Swimming spot they chose was excellent. If you're looking for the real deal, this is it. Loved hearing their stories about open ocean sailing and traversing the Caribbean Islands. Kids loved the aqua chair floaty. Worth every penny and more.

  2. HC

    Hazel

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    Bob and his wife Gabby are amazing. We had so much fun with them. The boat is gorgeous and Bob is clearly a seasoned captain. Thanks again!

  3. AS

    Andy

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    What a wonderful time out on beautiful lake Michigan with Captain Bob! First time my family and I have been on a sailboat and we learned so much! The views of the city coupled with the hospitality onboard made it a day to remember for sure! A+ Highly recommend!

  4. TW

    Ted

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    I was impressed that everything went according to plan. Met Captain Bob right on time and boarded what looked like an almost brand new boat. Very well maintained and extremely clean. First mate was first of all and offered water and refreshments for myself and my guest. Leaving the marina was professional and uneventful. The wind was light and variable and made for rather slow sailing but it was a great opportunity to hear some of the fine stories connected to Helios. For anyone that wants a true sailing experience and an opportunity to talk to some people that have been there done that, charter this sailboat! Thank you Captain, maybe we can have another adventure later in the summer.

  5. AS

    Ali

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    We had a wonderful time on Bob's boat! We felt safe and loved seeing the beautiful skyline! Would definitely do it again!