The Best Sailboat Rentals Near Lake Winnebago

AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

Steve was an amazing host. His itinerary was punctual and we could tell he spent the time researching just how to make our experience just what we were looking for. Steve was a great captain and the boat is perfect for a few hours out on the bay. Can’t wait to ride with Steve the next time we come to Annapolis

38-ft Hunter 376 Sailing Adventure in Annapolis

Alberto and his wife were absolutely wonderful hosts. They were welcoming, attentive, and made sure every detail of our sailing trip felt effortless. We had the most perfect day on the water, beautiful views, great company, and an experience we’ll remember for a long time. Highly recommend their boat and hospitality.

38-ft Hunter 376 Sailing Adventure in Annapolis

Alberto was great about communicating and flexible when we had to reschedule due to bad weather the first time. He and his wife hosted us, balancing chatting and talking with them and having our own time as friends. Definitely recommend and would book again

Private Cruise Onboard 32ft Hunter Legend Sailboat in Chicago

I am new to the world of sailing, and this was an awesome experience. I was able to have hands-on learning about sailing in the midst of a safe environment and a competent captain. As I don’t own, my own boat, the cost was very reasonable. I plan to do this again then near future!

AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

Stephen was great from the jump and the boat was as advertised. Great communication, super flexible with the itinerary. Made it super easy for our group to show up and be on our way.

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.