Commissioning Week

A Practical Luxury | An Essential Home Base

Commissioning Week is one of the most meaningful — and logistically demanding — weeks your family will ever plan.

Hotels in Annapolis during this time often exceed $850 per night per room, with families needing 4-5 separate room reservations for 8 nights, often spread across multiple properties.

Coordinating arrivals, meals, transportation, and family time can quickly start to feel like a second full-time job — right when you want to be fully present with your mid.

Fair Winds allows the week to unfold with ease. Everyone arrives, settles in, and stays together — close to the Yard, close to downtown, and close to one another. Logistics fade into the background, making room for what matters most.

(Typical Schedule Overview — events vary slightly by year)

⚓Commissioning Week Schedule

Many families tell us Fair Winds feels like a fitting capstone to this first Academy chapter — a place to pause, reflect, celebrate, and begin the next adventure together.

Located right in the heart of downtown Annapolis, just one block from the United States Naval Academy Yard and steps from the Harbor Waterfront on Prince George Street, Fair Winds places you at the center of it all — without sacrificing comfort, space, or privacy. There’s no shuttling between hotels, no coordinating rides across town — just the ease of having everyone together, where they need to be, when it matters most.

From the front door, you can walk to the Yard, the State Capitol, stadium, downtown restaurants, & waterfront - nearly every Commissioning Week event.

Fair Winds was curated with the USNA journey in mind. Throughout the home, you’ll find thoughtful nautical touches, artwork, and décor that reflect Naval Academy traditions, the midshipman experience, and the pride that comes with earning a commission. It’s a space that honors where they’ve been — and quietly celebrates where they’re headed next.

Rooted in History, Tradition, & Togetherness

Illustration of a blue and orange helicopter flying over Annapolis, Maryland, with multiple U.S. Navy aircraft flying around, a stadium, sailboats, and famous landmarks like the Maryland State House and Naval Academy.

Commissioning Week

  • 2025 Commissioning we had the privilege of hosting an alumni family at Fair Winds. After the week wrapped up, they shared this note with us:

    “Commissioning Week is emotional in a way that’s hard to put into words, and it passes so quickly. Having Fair Winds as our home for the week gave us a place to breathe. Somewhere our family could land, exhale, and be together.

    Our midshipman loved being able to come and go easily - walking back from the Yard between events, grabbing a real meal, taking a shower, and just being ‘home’ for a bit before heading back out. It felt grounding during a week that other parents expressed can feel overwhelming.

    As parents, having everyone under one roof mattered more than we expected. At the end of each day, we could sit together, talk through what we’d experienced, and just be present without worrying about logistics or coordinating plans across town.

    The house was comfortable, welcoming, and exactly what we needed; Fair Winds felt cared for, not staged. Amanda was easy to communicate with and clearly understood the rhythm and emotions of Commissioning Week, which made everything run smooth.

    Looking back, Fair Winds became an essential part of our Commissioning Week memories. We’re so grateful we stayed there and wouldn’t have changed a thing.”

  • Commissioning Week 2026 is fully reserved and paid in full by returning family guests. We do not anticipate any availability this year, and cancellations are extremely unlikely. As a result, we are no longer maintaining a waitlist for 2026.

  • Commissioning Week 2027 Stay Details

    Check-in: Friday, May 21, 2027
    Check-out: Sunday, May 30, 2027

    This timing allows your family to be in Annapolis for the entire stretch of Commissioning Week without moving mid-week or rushing departures, including:

    • Blue Angels practice flights and the official air show

    • On-Yard events and extended family time with your midshipman

    • Graduation Week ceremonies, celebrations, and gatherings

    • Hosting family and classmates comfortably in one place

    Rate & Payment Structure

    The total rate for the full 2027 Commissioning Week stay is $29,000.

    Because families are often planning several years ahead, we offer a long-term payment structure that many Navy families find helpful:

    • One time non-refundable deposit ($3,500) due at signing

    • Remaining $25,500 divided into three equal payments of $8,500, due on:

      • May 1, 2026

      • October 1, 2026

      • March 1, 2027

    Most families value the ability to secure a single, walkable home for the entire week while planning around clear, evenly spaced milestones as the years progress, but if alternate payment timing would be helpful, we’re happy to consider it, provided the full balance is received no later than March 1, 2027.

    If Fair Winds feels like the right fit, please simply reply to the Commissioning Week email and let us know. We’re also always happy to connect by phone/video to answer any remaining questions.

    Please note: We are currently speaking with several families regarding this opening. Reservations are confirmed on a first-confirmed basis once details are finalized.

  • Commissioning Week 2028 – Reserved

    Commissioning Week accommodations are typically secured well in advance, and availability at Fair Winds rarely changes once reserved. To ensure your family has lodging that meets your needs, we recommend confirming alternative accommodations now rather than waiting for an opening here.

    As a courtesy, we do maintain a small, private waitlist for families who feel Fair Winds would be the right fit. This list is intentionally limited and is nearly complete, with plans to close it soon. On the rare occasion that plans do shift, we reach out discreetly to waitlisted families before any availability is shared more broadly.

  • Commissioning Week 2029 – Reserved

    Families planning for Commissioning Week typically secure accommodations well in advance, and availability at Fair Winds rarely changes once reserved. To ensure your family has lodging that meets your needs, we recommend confirming alternative accommodations now rather than waiting for an opening here.

    As a courtesy, we do maintain a small, private waitlist for families who feel Fair Winds may be the right fit. This list is nearly full, and we are only accepting a limited number of additional names. On the rare occasion that plans do shift, we reach out discreetly to waitlisted families before any availability is shared more broadly.

  • Commissioning Week 2030 – Not Quite Yet

    It’s a bit early to reserve for Commissioning Week 2030. Induction Day for the Class of 2030 hasn’t been announced yet, and most families are still at the very beginning of their Naval Academy journey.

    We typically open reservations after Plebe Parent Weekend (around August–September 2026). By then, families have had time to experience Academy life firsthand and better understand the pace, commitment, and rhythm of the road ahead. Dates, logistics, and long-term planning tend to come into much clearer focus — as does your plebe’s enthusiasm for the journey ahead.

    Additional details and timing will be shared once reservations for 2030 officially open.

Aerial view of five blue fighter jets flying in formation over a river, creating white vapor trails, with spectators on a waterfront promenade watching.
People dressed in white suits watching a jet flyover during an airshow. White Uniforms - Blue Angels
Line of military personnel in uniform carrying flags on a grassy field.