Learn to Cruise • Basic Coastal Cruising

After mastering the fundamentals, our Basic Cruising program introduces sailors to more advanced topics and sailing in diverse conditions.  You will learn to cruise: be prepared for extended sailing, planning for new waters, adverse weather and troubleshooting. By the end of the course, students will have the skills to plan a full day or overnight cruise, and the confidence to execute it safely and enjoyably.


  • In Person and Online
  • 2 days Small Group Instruction
  • Advanced Online Training
  • Skipper Certification & NauticEd Membership
  • Guaranteed Competency
  • Prices & Registration

Prerequisite: Skipper-Small Keelboat, ASA101, or equivalent experience required.

2 Days Small Group Instruction

Courses are kept small for personalized instruction, and our instructors are highly experienced sailors and USCG Captains. The weekend will be spent both in the classroom (a little) and on the water (a lot), and the emphasis is on learning and practicing practical skills.read more

By the end of the class, the instructor will verify your competency at a Skipper level, which means the instructor is confident in your abilities to sail or crew without him.

Some examples of what you'll learn and practice:

  • Advanced sailing theory
  • Managing heel and weather helm
  • Sail shape and rig control
  • Heaving to, heavy weather techniques, and reefing underway
  • Anchoring techniques
  • Handling emergencies, docking under sail, and man overboard recovery
  • Course plotting and steering by the compass

By the end of the course, students will have the skills to plan a full day or overnight cruise, and the confidence to execute it safely and enjoyably.  And, we guarantee competency!

Advanced Online Knowledge Training

NauticEd Worlds most advanced sailing education. Click and receive 2 free online sailing courses.Learning to cruise involves strengthening core competencies (sail trim, boat handling, etc...) as well as learning more boat systems, weather and esp. boat handling techniques.For knowledge, we offer NauticEd's online courses to prepare you with the most advanced and current online sailing education available.  Start immediately, take your time with interactive content, and test online.read more

When you sign-up, you'll receive a NauticEd account that includes the following courses:

Skipper Online Clinic - topics include (full description at NauticEd Skipper Course):

  • Weather and Sea Conditions
  • Electrical Systems
  • Auxiliary Power
  • Rigging: Standing and Running
  • Rules of the Road
  • Slip Departure and Return
  • Sailing
  • Communications & Navigation
  • Anchoring and Mooring
  • Coping with Emergencies

Online Maneuvering Under Power Clinic (full description at NauticEd Maneuvering Under Power Clinic)

  • Beginner to advanced maneuvering skills
  • How to dock a large sailboat
  • How to reverse your boat into a slip with ease
  • How to handle high winds from any direction when docking
  • How to use prop walk to your advantage
  • How not to get pushed around by the wind
  • How to maneuver a sailboat in a tight marina with high winds

Basic Sail Trim Course - topics include (full description at NauticEd Basic Sail Trim):

  • Basic sail trim concepts
  • Apparent wind
  • Reduced Drag
  • Angle of attack

And, we suggest Navigational Rules Clinic - topics include (full description at NauticEd Navigational Rules):

  • Why "Right of Way" is more properly called "Stand On"
  • Essential knowledge regarding the Rules with other vessels
  • How not to get squashed like a bug by big container ships
  • Who gives way between power driven vessels and sailboats
  • When sailboats must give way to other vessels
  • When Sailboats give way to each other
  • You'll be presented with realistic illustrated situations

Skipper Small Keelboat Certification

Learn to Cruise and sail further and faster with improved sail and boat handling techniques, in heavier weather and with sailboats 25' and larger.

Certification requires you pass all the competency tests listed below. With NauticEd it's really simple: when you sign-up, you'll be given access to an online resume that records your online training, instructor sign-offs and experience. Skipper certification requires Skipper knowledge training as well as Maneuvering under Power (to learn boat-handling skills), Practical competency in our 2-day on-the-water course and a minimum 4 days qualified sailing experience (which, by now, you probably already have).read more

Each step is recorded in your online resume, and once ALL the required steps are achieved - you're certified. Certification requires successfully passing the following competency requirements:

√ Knowledge: Successfully Complete Online Skipper and Maneuvering Under Power classes
√ Practical Competency: 2-day course
√ Experience: 4 days of qualified sailing experience (prior experience counts)

The additional days of experience are required to demonstrate that you can successfully skipper on your own, utilizing what you learned online and on-the-water.  The days are logged into your NaucticEd online logbook and once completed - you're certified! For more information, see Sailing Certification.

Guaranteed Practical Competency

Simply, you're paying us to learn to sail at a certain level (not for a certain number of hours).read more

We guarantee that in practical courses your instructor will verify your practical competency.  By this we mean that Island Sailing management cannot override instructor decisions; and towards the end of the practical course your instructor will decide whether you're sufficiently trained (or not).  Sometimes the instructor may want to reschedule if the weather's uncooperative, or they may feel a particular student may need additional instruction or mentoring on certain topics.  If the instructor feels as you're not trainable as a competent sailor (which has never happened in our 35+ years), then we'll refund the practical portion of your class.

And, if you're not satisfied with your instructor, then you can retake the course at no additional charge.


Learn to Cruise - Skipper  $530.00 per sailor (Members $477.00)

*If you've already completed NauticEd Skipper online clinic, then $490.00 per Sailor (Members $437.00)

What's Included:

  • Online Clinics: Skipper, Maneuvering Under Power, Basic Sail Trim, Basic Navigational Rules (optional).
  • 2 days Small Group Instruction with Guaranteed Competency.
  • NauticEd Skipper Certification Rank once all certification requirements are achieved.
  • NauticEd Membership and Online Resume.


To register online, select a class date to begin registration. Please complete the form and process for each student as we need those details for the class.... *note: if a member, please contact us to book directly with Member Discounts.

Class Booking Conditions (Deposits, Refunds and Cancellations) are detailed here >

Certainly contact us at (503) 285-7765 or info@islandsailingclub.com to sign-up over the phone or with questions.

Payment is through PayPal's secure server, which accepts major credit cards as well as PayPal options.

Paypal Payment Options

*note: dates are the beginning day of the class

Upcoming events

  • May13Sat
    Basic Cruising - Portland
    10:00Island Sailing, 515 NE Tomahawk Island Drive, Portland, OR 97217
  • Jun10Sat
    Basic Cruising - Portland
    10:00Island Sailing, 515 NE Tomahawk Island Drive, Portland, OR 97217
  • Jul08Sat
    Basic Cruising - Portland
    10:00Island Sailing, 515 NE Tomahawk Island Drive, Portland, OR 97217
  • Aug12Sat
    Basic Cruising - Portland
    10:00Island Sailing, 515 NE Tomahawk Island Drive, Portland, OR 97217
Show more

What our students say about learning to cruise...

Basic Cruising Course, Capt. Somervell, 10/25/16, 4.4/5 rating

Lisa B.Vancouver WA

Basic Cruising Course, Capt. Somervell, 10/24/16, 4.4/5 rating

John B.Vancouver WA

Basic Cruising Course, Capt. Somervell, 09/29/16, 5/5 rating

Instructor Alan Somervell was friendly and professional, and displayed a high degree of sailing knowledge.

Timothy M.Portland OR

Basic Cruising Course, Capt. Frankland, 09/13/16, 5/5 rating

I feel confidant I will be able to reach my goals, which may be many foreign shores

Robert R.Portland OR

Basic Cruising Course, Capt. Somervell, 09/12/16, 5/5 rating

Great time and learned a bunch! Thanks Alan!!

George C.Kirkland WA

Basic Cruising Course, Capt. Somervell, 09/11/16, 5/5 rating

Alan is an exceptional instructure. I learned more practical skills with him in 2 days than I had in months of sailing.

Richard H.Mill Creek WA

Basic Cruising Course, Capt. Somervell, 09/11/16, 5/5 rating

Alan is an amazing sailing instructor. I learned more from him in the past two days than I have ever learned in weekend or week for that matter. Seriously, ever moment was a learning experience. Everything he said was relevant, clearly stated, and practical. His is truly the best of the best, and I would recommend him to anyone without hesitation. He is without a doubt a master at his trade.

Mark T.Bothell WA

Basic Cruising Course, Capt. Frankland, 08/20/16, 5/5 rating

We greatly appreciate Stephen’s skill, knowledge, and the ability to teach and translate the sailing curriculum so that we could both understand it and also apply it.

Tom S.Tigard OR

Basic Sailing Course, Capt. Powning, 07/19/16, 5/5 rating

Nat was an amazing instructor- I was lucky to benefit from his incredible knowledge. He is an amazing asset for Island Sailing. I will recommend him highly.

Ismail P.Portland OR

Basic Cruising Course, Capt. Frankland, 04/12/16, 5/5 rating

Very capable and competent skipper and instructor. Enthusiasm for sailing and introducing others to it is inspiring.

Chris K.Burbank WA