J World Annapolis
1
Our beginner level courses are designed to insure you get off to a smooth start. You will be placed aboard with other students of similar experience.
Basic Cruising
Basic Keelboat
Bareboat Cruising
Coastal Navigation
2
The Chesapeake Boating Club is the only overnight boating club in Maryland. Enjoy the opportunity to cruise up and down the Chesapeake Bay.
Sailboats
Powerboats
Overnight Cruising
3
Our intermediate level courses are designed for sailors familiar with the basics who are looking to expand their skills and confidence and move into either cruising or racing.
Spinnaker & Race Boat Handling
Racing
4
Sail Trim and Balance
USCG Nautical Rules of the Road
VHF Radio Knowledge and Operation
Navionics
Nautical Arithmetic
Marine Weather
Charter Sailing Vacations
Chesapeake Boating Club at J World Annapolis
The Chesapeake Boating Club at J World Annapolis is the only overnight boating club in Maryland. Enjoy the opportunity to cruise up and down the Chesapeake Bay. An overnight stay on one of our boats is cheaper and more fulfilling than a vacation in a hotel.
We believe boating should be flexible, fun and affordable! That belief drove us to open for business in 1992 in the Historic Eastport section of Annapolis, and that commitment has made us what we are today - The #1 flexible boat sharing program on the Chesapeake Bay. Let us help you experience the thrill of boating at a fraction of the cost of ownership.
32 Boats Waiting
Choose the right boat for any adventure - Sail and Power from 17' - 36'
Easy Access
Located only .5 miles from the heart of Annapolis, and .3 miles to open water
Boating Seminars
We offer both in-person and online educational seminars by our renowned J World coaches in the off season.

For Members

Bookings at J World Annapolis

All Offerings – J World Annapolis

Since 1992, J World Annapolis and the Chesapeake Boating Club has been providing the very best in coaching, instruction, and boat usage to new and experienced boaters from around the world.

Memberships at J World Annapolis

Upgrade Membership – J World Annapolis

Forgot your membership number? Use our Membership Lookup. The Chesapeake Boating Club was founded in 1992 to provide flexible a...

Memberships at J World Annapolis

Membership Lookup

Look up your membership number using your email address.

General Information

Courses at J World Annapolis

Courses & Seminars – J World Annapolis

Since 1992, J World Annapolis and the Chesapeake Boating Club has been providing the very best in coaching, instruction, and boat usage to new and experienced boaters from around the world.

Memberships at J World Annapolis

Become a Member – J World Annapolis

The Chesapeake Boating Club was founded in 1992 to provide flexible and affordable access to high quality and easy to use boats - available on short notice and at a fraction of the cost of ownership. Becoming a member is a perfect way to get on the water and enjoy boating with minimal expense and hassle.

Flotilla at J World Annapolis

Vote for our Destination – Annual Flotilla – J World Annapolis

Discover Paradise: Join Our Island and European Flotilla Adventures! Vote below for our destination - Europe or the Caribbean?

WhatsApp.com

Chesapeake Boating Club

WhatsApp Group Invite - Join the conversation

Thursday Night Races
J World Annapolis invites you to enter your Lightning, J/22, J/24, J/70 or J/80 class boats for our current season of Thursday Night One Design Racing on the Severn River in Annapolis. We are pleased to announce that this year’s season will be made even better by the support and official sponsorship of Ullman Sails and the full season support with our partner Severn Sailing Association (SSA).

Clubspot

J World Thursday Night Racing

J World Thursday Night Racing 2025 event details.

Team Building


Through J World, named the top sailing school in the country by Practical Sailor magazine, we offer team building training and outings using the growing sport of team sailing. Its team development, with wind at your back and spray on your face. An unforgettable experience for your team!
  • Communication Leadership
  • Team Dynamics
  • Cooperation
  • Group Participation
  • Problem Solving
  • Strategic Planning
  • Immediate Feedback
Get out of the conference room and onto the water! We have, through years of experience and hundreds of team building events, created three “off the shelf” programs that represent what we most commonly receive as team building requests. Keep in mind we can customize or invent any program to suit your teams particular needs. All programs include a heavy dose of fun, camaraderie, and group development. All programs are available in both full day and half day options.

Sailworks

If you are looking for the premiere sailing related team building event, this is it! The goal of this program is not to teach participants how to sail, but rather to use the challenging sport of sailing to encourage your team to work together in a new environment. Benefits of this program include increased esprit de corps, better communication, and more effective leadership among your team. Sailworks is a multi-boat team exercise with groups of four participants and a coach on each boat focusing their energies on a specific group challenge. While the challenge is not a “race”, getting through the course will require collaboration of all participants to navigate the course, wind and currents..all under the direction of a trained, professional coach. Communication will be critical as an overall strategy must be implemented by multiple strategists operating from remote locations (different boats).

Harbor Cruise/Fun Sail

The primary focus of the Harbor Cruise is a fun day on the water in scenic Annapolis. This is not a boat ride. Your group will how to work together to maneuver their sailboats. Then put their skills to the test navigating the crowded Annapolis harbor.

J World Regatta

Participants will get the chance to compete against their fellow team members in a sailboat race! After an on the water coaching session, where the teams will focus on getting the sailboat around the course we will hold a regatta for the participating teams. Particular good program for highly competitive sales teams, develops small team synergy and dynamic communication skills while maintaining a competitive spirit.