The Best Team building Experience for High Performance Teams
Schooner Woodwind specializes in providing your group with the best and most unique team building sailing experience in Annapolis or anywhere! Our professional captains and crew lead an exciting, hands-on sail training program on the Chesapeake aboard our 74-foot schooners Woodwind and Woodwind II.
Our three signature team building programs are highlighted below. Click on any one, to get to a comprehensive description. If you don’t find what you’re looking for, or require a less intense or more intense team building program tailored to your group’s specific needs, please call our helpful, experienced team building staff at 410-263-1981 to plan your team event.
Teambuilding Fun
Intensity Level
The captain and crew will introduce your group to the core elements of sailing and teamwork, inviting those interested to take a hands-on-role in this memorable teambuilding experience.
| Boats: | 1 |
| Ideal Group: | 7-35 |
| Minimum Time: | 3 Hours |
| Catering: | Terrific gourmet food & drinks |
This relaxing sailing experience is perfect for celebrating milestones or building relationships. An interactive sail on the Chesapeake Bay is a great way to welcome new members, get to know each other, or reward team accomplishments.
Team Challenge

Intensity Level
This exciting and interactive experience is ideal for building the core skills that create a high performance team. Increase awareness of your team process. Learn how pressure stimulates teamwork. Understand how leadership is applied in a team environment.
| Boats: | 1 |
| Ideal Group: | 7-35 |
| Minimum Time: | 3 Hours |
| Catering: | Snacks, and bagged lunch options |
Your team will be divided into smaller groups to learn the basics of sailing, communication and teamwork. After training, the entire team will work together to sail and successfully navigate around a course.

Ultimate Team Challenge


Intensity Level
Two teams on identical schooners go head-to-head in an exhilarating, fun, and interactive ‘America’s Cup Style’ match race for the entire group. Awaken your team’s competitive juices, as everyone works together to be first over the finish line.
| Boats: | 2 |
| Ideal Group: | 14-50 |
| Minimum Time: | 4.5 Hours |
| Catering: | Snacks, and bagged lunch options |
Each team will be divided into smaller groups for an intensive sail training and teamwork session. This teambuilding program has the biggest challenge, where the best teamwork wins.











