BVI Cruising Course

Escape Chicago's Winter

Join us on this epic adventure of sailing, snorkeling, beaches, and sun!

Our Live-Aboard Cruising & Seamanship 301 combines learning with an adventure-packed vacation. Over the course of 7 days you and your certified instructor will plan, manage, and sail a comprehensive Caribbean cruising adventure. You will master all aspects of cruising. This includes sea crossings, night sailing, course planning, and systems management. By the end of your journey, you will possess the skills necessary to pilot a sailboat to any horizon! You will also have three internationally recognized US Sailing certifications: Basic Cruising, Bareboat Cruising and International Proficiency Certificate. Under the guidance of our certified instructor and captain you will learn every aspect of cruising. This includes provisioning and prep, trip planning, open water sailing, and some basic piloting. You will experience the joy of making exciting new landfalls, the epitome of a cruising lifestyle.


We do NOT teach basic sailing during this trip. Participants wanting to earn their Basic & Bareboat Cruising certs should be able to confidently command and control a sailing vessel. 

US Sailing’s International Proficiency Certificate

If you desire to charter a sailboat in the Mediterranean, we recommend obtaining a US Sailing International Proficiency Certificate© to simplify the charter process and operate a vessel in compliance with EU law.

In order to make it easier for cruising sailors from the U.S. to charter sailboats in the European Union (EU), US Sailing has created a simple certification program for cruising sailors seeking to charter sailboats in European Union waters. The International Proficiency Certificate©, an extension of US Sailing’s current Keelboat Certification System, allows sailors who have completed a US Sailing Bareboat Cruising course to charter sailboats without a captain in EU waters.

The International Proficiency Certificate© works much like a driver’s license for a car. The certificate must be presented to a charter company to obtain a boat, and then carried aboard at all times while sailing in EU waters.  The certificate is good for five years from the date of issue.

Course Information

-Week 1: February 7-14, 2020
Destination: Road Town, Tortola, BVI
Course Duration: 7 Days
Prerequisites: US Sailing Basic Keelboat Certificate
Cost: $2,400/Person Shared Berth; $3,200/Person Single Berth
Includes: Includes: Provisions, Captain & Mate, Course Materials
Vessel: 45-50ft Monohull

Course Objectives

  • Confident command of a cruising vessel
  • Sea Crossings
  • Night Sailing
  • Onboard systems management
  • Safety and Emergency Procedures for cruising vessels
  • Two US Sailing Certifications (Basic & Bareboat Cruising) & International Proficiency Certificate


Andrew Papp

The BVI Cruising Course was truly an experience of a lifetime, more than I ever could have expected. The friendly locals, phenomenal food, and beautiful sailing were remarkable every day. This course gave me confidence to make such a trip on my own. I'm already making plans to do it again!  I am happy that ‘I DID IT’ rather than ‘I WISH I had done it’.


Joanne W

Sailing the British Virgin Islands with Chicago Sailing was an unparalleled experience.  During the week, there is plenty of opportunity for you to experience just about every aspect of sailing.  And I'm proud to say I can tie a bowline with my eyes closed.  Having never done a trip like this before, I must tell you:  I. Had. So. Much. Fun.  I am already asking When can we do this AGAIN??!!