Plebe Summer Sailing (And Beyond!)

Jul 08, 2025

The Foundation: Plebe Summer Sailing

Every Midshipman's sailing experience begins during Plebe Summer with Basic Sail Training (BST). This introductory program serves as a cornerstone of naval education, teaching fundamental maritime concepts that will prove valuable throughout their naval careers.

During BST, Plebes learn:

Basic parts of a sailboat
Essential nautical terminology
Fundamental sailing techniques

The training takes place on Colgate 26 boats, which the Naval Academy has rebranded as Navy 26s. These 26-foot sloops provide an ideal platform for beginners to grasp the basics of sailing.

What makes this experience particularly enjoyable for many Plebes is that the instructors are often recent graduates waiting for their fleet assignments. This creates a more relaxed learning environment, offering a welcome respite from the rigors of Plebe Summer. It's a casual introduction, not a masters degree in sailing.

I remember not learning a SINGLE THING during Plebe Sailing because I was so excited to be able to sit down and just relax for a minute.

So unfortunately if you thought your midshipman was going to be able to take you out on the Chesapeake Bay after Plebe Summer... I'm sorry to say this, but probably not!

But if they do want to learn how to sail (FOR REAL), there are options to continue into the Academic year.

Sailing Beyond Plebe Summer

For Midshipmen who develop a passion for sailing during their Plebe Summer, the Naval Academy offers numerous opportunities to continue honing their skills. These include:

1. Offshore Sail Training Squadron (OSTS)

This program, typically undertaken during a Midshipman's Youngster (sophomore) year, offers an immersive sailing experience. Participants spend a month sailing on Navy 44s, larger vessels designed for offshore sailing. The program includes:

Training sails out of Annapolis
A week-long trip to Newport, Rhode Island
Practical application of navigation and seamanship skills

2. Varsity Sailing Teams

The Naval Academy boasts two intercollegiate sailing teams:

Intercollegiate (IC) Sailing Team: This team focuses on dinghy racing, competing against other top collegiate sailing programs.
Offshore Sailing Team: This team participates in big boat racing, often competing in prestigious regattas up and down the East Coast.

The Offshore Sailing Team: A Unique Leadership Laboratory

The Offshore Sailing Team offers an unparalleled leadership development opportunity. Unlike many other varsity sports, this team doesn't recruit. Instead, it's open to any Midshipman willing to learn and work hard.

Key aspects of the Offshore Sailing Team include:

Year-round training: The team maintains its varsity status throughout the academic year, with winter months dedicated to classroom instruction and skill development.
Diverse fleet: Midshipmen sail on Navy 44s and donated vessels, some of which are high-performance racing yachts.
Prestigious competitions: The team participates in renowned races like the Newport Bermuda Race and the Annapolis to Newport Race.
Leadership roles: Rising seniors have the opportunity to become skippers, taking command of a boat and crew - a significant leadership responsibility.

Rivalries and Competitions

While Army-Navy rivalries dominate many USNA sports, sailing is different. The primary collegiate rivals for Navy sailing are:

U.S. Coast Guard Academy
U.S. Merchant Marine Academy (Kings Point)

These rivalries extend beyond collegiate regattas, as teams often encounter each other at various summer sailing events.

Why Consider Navy Sailing?

Participating in the Navy sailing program offers numerous benefits:

Advanced leadership opportunities: Midshipmen gain real-world experience in small unit leadership and decision-making.
Technical skills: Sailors develop a deep understanding of navigation, weather patterns, and mechanical systems.
Networking: The sailing world provides unique opportunities to connect with civilians and future naval leaders alike.
Career preparation: The skills developed through sailing often translate well to various naval career paths, including aviation and surface warfare.

If you want to learn more about the sailing program, and hear stories about Plebe Summer sailing, then check out the podcast below!!

Watch the interview on YouTube here

Listen to the Podcast on Apple Podcasts here

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Founder of Academy Insider and Podcast Host Grant Vermeer

Grant Vermeer is the founder of Academy Insider and the host of The Academy Insider podcast. He was a recruited athlete which brought him to Annapolis where he was a four-year member of the varsity basketball team.

He was a cyber operations major and commissioned into the Cryptologic Warfare Community. He was stationed at Fort Meade and supported the Subsurface Direct Support mission.

He separated from the Navy in 2023 and now owns The Vermeer Group, a residential real estate company that specializes in serving the United States Naval Academy community with nationwide consulting and connection.