The Story Behind Fair Winds
Rooted in Naval Academy tradition and inspired by meaningful moments, Fair Winds was created as a place to gather, celebrate, and reflect.
A Connection to the Naval Academy
Fair Winds is deeply connected to the traditions and spirit of the U.S. Naval Academy. Located just one block away, the home reflects a deep appreciation for the people, milestones, and experiences that bring families to Annapolis year after year.
For many guests, their time in Annapolis marks a meaningful chapter — whether celebrating Commissioning Week, reconnecting with alumni roots, or simply experiencing the history and character of the Academy.
What Inspired Our Name
“Fair winds and following seas” is a traditional naval expression, often used to wish someone well as they embark on a new journey. It reflects both a sense of optimism and the significance of life’s transitions — sentiments that are deeply tied to the experiences shared in Annapolis.
The name represents the spirit of the home: a place where guests gather to celebrate milestones, create memories, and begin new chapters.
Our North Star
At the heart of Fair Winds is a simple idea: to create a space where people can come together in meaningful ways.
Whether celebrating a milestone, spending time with family, or experiencing Annapolis for the first time, the goal is to provide a home that feels both welcoming and memorable —
a place that reflects the significance of the moments shared within it.
At the Helm
As hosts, we are passionate about creating a thoughtful and welcoming experience for every guest. Fair Winds was designed not just as a place to stay, but as a place to gather — one that reflects the character of Annapolis and the traditions that make it so meaningful.
We hope that every stay here becomes part of your own story.
The Lucky Bag
The Naval Academy’s “Lucky Bag” yearbook represents a collection of memories, traditions, and shared experiences.
Fair Winds was inspired by this idea — a place where meaningful moments are gathered and remembered. From milestone celebrations to quiet time with family, the home is designed to hold experiences that become part of something lasting.