SailTime Milwaukee and Racine

Learn to Sail

ASA Awarded SailTime Milwaukee Sailing School 

2012 ASA Outstanding Sailing School of the Year

 (in the top 20 of all ASA sailing schools worldwide)

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

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

Our ASA 101 classes start at $450 with a discounts for 2 or more people who sign up together.

We also have a Discover Sailing classes starting at $195

Request current class pricing

Our ASA certified Sailing School offers the following class:

ASA 101 Basic Keel boat in Racine
ASA 101 Basic Keel boat in Milwaukee
ASA 103 Coastal Cruising in Milwaukee
ASA 104 Bareboat Charter in Milwaukee
ASA 103/104 Combo in Milwaukee
ASA 106 Advanced Coastal Cruising in Milwaukee
ASA 118 Docking Endorsement in Racine
ASA 118 Docking Endorsement in Milwaukee
ASA 105 Coastal Navigation
ASA 120 Radar Endorsement

Overviews of courses provided by SailTime Milwaukee can be found at:  Sailing course descriptions

ASA course standards can be found at:  ASA Standards

Sailing School Instructors

Captain Jim Stewart (ASA Outstanding Instructors for 2009), 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. 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 and Racine, WI.

The SailTime Training Difference

Our approach to sail 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 10 a.m. and goes until 6 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 required. 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 allow 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, WI and Racine, WI. Both locations are an easy drive for the seafaring residents in and around the area that want to expand their boating knowledge and skills. Racine’s revitalized downtown area and seaside ambiance provide a great getaway that will allow you to combine your training experience with a mini-vacation for the entire family. Access to convenient, nearby hotels and B&Bs enable us to set sail on Lake Michigan in minutes while other members of your party experience a coastal getaway.


If you have any questions or would like to talk sailing please call 262-960-1470 or email us at