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.

This opening became available due to an unexpected change in plans for the family who had previously reserved the home. While situations like this are uncommon once families move past key milestones in the Naval Academy journey, we’re mindful of their privacy and don’t share details.

Because this availability arose after 2-for-7, most families who had previously inquired have already finalized other accommodations. As a result, Fair Winds is now available for Commissioning Week 2027 on a first-confirmed basis, and we do not expect it to remain open for long.

During Commissioning Week, hotels in Annapolis frequently exceed $850 per night per room, with many families needing four to five rooms for eight or more nights — often spread across multiple properties and well outside walking distance of the Yard. When room totals, transportation, and the time required to coordinate everyone are taken into account, overall costs commonly reach — and often exceed — $35,000–$40,000, not including the added stress of managing logistics throughout the week.

At first glance, a private home like Fair Winds may feel like a significant investment. In practice, it offers something hotels simply can’t: one walkable home, one set of logistics, and the ability for everyone to stay together. Families move easily between ceremonies, family time, and moments of rest — without shuttles, reservations, or constant coordination. Everyone arrives, settles in, and stays put, allowing the week to unfold with far more ease and intention.

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 $30,000.

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

10% non-refundable deposit ($3,000) due at signing
Remaining $27,000 divided into three equal payments of $9,000, 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, requesting contracts. We’re always glad to connect by phone/video to talk through payment schedules and 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.