SailTime Milwaukee and Racine

Sailing School

SailTime Milwaukee Sailing School 

An Award Winning ASA Sailing School

 If you are looking for classes as a beginner to learn to sail, or you want to advance your current sailing knowledge and skills through additional classes, we have the right course for you.

SailTime Wisconsin’s Sailing School is committed to providing the highest quality sailing courses to both our members and the general public. We use a Hunter 38 and a Hunter 33 in our training classes.  Through the sailing school, we offer the following ASA-approved sailing courses with a typical class size of 2-4 students.

Request current class pricing

Our ASA 101 classes start at $500 with a discount for 2 or more people who sign up together.

Our ASA certified Sailing School offers the following training:

  • ASA 101 Basic Keelboat in Racine, Milwaukee, Kenosha
  • ASA 103 Coastal Cruising in Racine, Milwaukee, Kenosha
  • ASA 104 Bareboat Charter in Racine, Milwaukee, Kenosha
  • ASA 103/104 Combo in Racine, Milwaukee, Kenosha
  • ASA 105 Coastal Navigation
  • ASA 106 Advanced Coastal Cruising in Racine, Milwaukee
  • ASA 118 Docking Endorsement in Racine, Milwaukee, Kenosha
  • ASA 120 Radar Endorsement

Overviews of courses provided by SailTime Milwaukee can be found at the following link:

  Sailing course descriptions

ASA course standards can be found here:  ASA Standards

Sailing School Instructors

Captain Jim Stewart (ASA Outstanding Instructors for 2009, 2013, and 2014), our Manager of Training, has been sailing for over 25 years. This skilled instructor has chartered boats throughout the US, Canada, Mexico, and the Caribbean; and has been training others to sail for more than five years here in southeast Wisconsin, and Chicago, Illinois. Captain Stewart has a 50-ton master’s license and is certified to teach several courses SailTime provides, including ASA 101 through ASA 106 (Basic Keelboat through Advanced Coastal Cruising). He is currently handling SailTime’s Regional Training Center in Milwaukee, Racine, and Kenosha WI.

The SailTime Training Difference

Our approach to training is different than most. We restrict our sailing class size to two to
four on a boat, and we train on cruising class boats, instead of small, open-deck day sailboats. Our students enjoy the comfort of knowing that they won’t get wet by capsizing or run the risk of meeting the boom while tacking. Since all of our boats are equipped with roller-furling jibs AND mainsails, students will be trained on the modern rigs that are becoming common in the larger charter fleets around the world. Having fewer students on a boat makes it possible for everyone to get plenty of practice time, both at the wheel, and developing crew skills. Our typical training day starts at 9 a.m. and goes until 5 p.m. We train during relatively quiet weekday periods, so students can learn without encountering the weekend harbor traffic.

A concentrated effort is put into learning how to handle the boat under power in and around the harbor and slips. These skills allow our students to gain confidence at the helm even on the busy weekends. First-mate training can also be provided at 50% off the standard rate. First-mate instruction does not result in any certification and no exam is given. The course is intended for a spouse or friend that will be a frequent sailing companion and focuses on crew skills for these individuals.  It also allows them to have a safe and enjoyable time on the water while building confidence.

SailTime Wisconsin’s ASA Sailing School

Located between Chicago, IL and Milwaukee, WI, the SailTime Wisconsin’s Sailing School provides cruising class instruction in Milwaukee, Racine, and Kenosha, WI. All three locations are an easy drive for the seafaring residents in and around the area that wants to expand their boating knowledge and skills. You can also find great local entertainment, lodging, and food just minutes from all three marinas.

If you have any questions or would like to talk sailing please call 262-825-4123 or email us at