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04-January-2027 Local Adventures & Superhost Shawn’s Travels
Commissioning Week at the United States Naval Academy in Annapolis, Maryland, is one of the most important weeks of the year for graduating midshipmen and their families. After four demanding years, parents, grandparents, siblings, friends, and other loved ones arrive to celebrate a remarkable accomplishment and the beginning of a new chapter of military service.
If you're traveling to Annapolis for Navy graduation, finding the right place to stay is worth planning early, particularly when several generations of a family are coming together.
Annapolis has hotels, historic inns, and short-term rentals. But families who want to stay together may also want to look beyond downtown for a waterfront vacation home with a kitchen, shared living spaces, and room to spread out.
That's where Chesapeake Paradise, a waterfront property in Deale, Maryland, south of Annapolis, may be worth considering. We offer five different accommodations, from a spacious family home to smaller private suites, with several ways to arrange a stay depending on your group's needs.
Commissioning Week is the U.S. Naval Academy's annual celebration leading up to graduation and the commissioning of its graduating midshipmen as officers.
Usually held in May, the week brings families and visitors to Annapolis for military ceremonies, performances, receptions, and celebrations. Graduation and commissioning mark the culmination of four years at the Academy and the beginning of service as Navy ensigns or Marine Corps second lieutenants.
Among the traditions and events that may be included are:
Graduation and commissioning ceremony: Held at Navy-Marine Corps Memorial Stadium in recent years, this is the centerpiece of the celebration.
Blue Angels flight demonstration: The Navy's flight demonstration squadron traditionally performs over the Severn River during Commissioning Week, weather and operational conditions permitting.
Color Parade: A formal military tradition showcasing the Brigade of Midshipmen.
Herndon Monument Climb: A well-known Naval Academy tradition in which plebes work together to climb the greased monument, marking a major milestone in their Academy experience.
Awards, concerts, religious services, receptions, and graduation-related celebrations: Individual events may have invitations, ticket requirements, or access restrictions.
The exact schedule, locations, and attendance rules change from year to year. For the most reliable current information, see the Naval Academy's official Commissioning Week schedule.
The celebration generally takes place in May, with the graduating class's commissioning ceremony concluding the major events.
Because the Academy updates its schedule annually, it's important to check the official Commissioning Week information before arranging travel, tickets, or activities.
Families may arrive several days before graduation to attend ceremonies and spend time with their midshipmen. Your exact arrival and departure dates will depend on which events your family plans to attend.
If you're booking accommodations well in advance, it's wise to consider your full schedule rather than focusing only on graduation day.
The best location depends on what matters most to your family.
For travelers who want to walk to downtown Annapolis restaurants or spend most of their time near the Naval Academy, a downtown hotel or inn may be the most convenient choice.
But extended families often have different priorities. Grandparents may appreciate a comfortable place to rest between events, while siblings or relatives who have traveled a long distance may want time to catch up together. Having a kitchen, a dining table, and inviting common areas can make coordinating meals and schedules much easier.
A vacation rental outside downtown can be particularly appealing when you're traveling with several households.
Chesapeake Paradise is in Deale, Maryland, on the western shore of the Chesapeake Bay, south of Annapolis. It's a drive to the Naval Academy and graduation venues—not a walkable downtown accommodation—but it offers a different experience from staying in a hotel.
Our property sits on about two waterfront acres, with a private pier and outdoor spaces overlooking Broadwater Creek near the West River and Chesapeake Bay. Guests can spend time on the lawn, watch the water from the porch or balconies, or enjoy a meal together after the day's events.
For a family celebrating a Naval Academy graduate, it can be nice to have a place where everyone can gather without having to meet in a hotel lobby or arrange every meal at a restaurant.
We have five distinct accommodations, and the right choice depends on your group size, preferred room arrangements, and availability.
Our Chesapeake Paradise House is the most spacious option, with six or more bedrooms, four bathrooms, a full kitchen, dining and living spaces, and waterfront views.
The house is particularly worth considering when parents, grandparents, siblings, and other relatives want to stay together. There are multiple areas where people can spend time separately, including upstairs suites, along with common spaces for meals and family conversations.
One of my favorite features is the large living area opening onto the screened porch. Guests can enjoy the water views from both spaces, and there's plenty of opportunity for the family to get together around the table.
If your family needs a substantial home but not the entire house, explore Chesapeake Paradise LITE.
This four- to five-bedroom, three-bathroom configuration provides access to a large portion of the house, including shared family living and dining areas, while another part of the building may be occupied separately.
It's an option for families who want a kitchen and room to spend time together but don't require all of the upstairs accommodations.
Our Waterfront Wonder Cottage is a separate three-bedroom, two-bathroom home next to the main Chesapeake Paradise property.
It has its own kitchen and living spaces, with lovely waterfront surroundings. It may suit a smaller family group, or relatives who want their own home near others staying at Chesapeake Paradise.
A guest who stayed with her family described it this way: “Our whole family loved the stay at the cottage.”
The Sky-Lit Flat + Solarium is a private upstairs apartment with its own entrance, an especially spacious bathroom, and a Solarium bedroom with walls of windows and a balcony overlooking the water.
It's a lovely possibility for a couple or smaller group that wants a little privacy, particularly when relatives have booked a larger accommodation elsewhere.
The Sunrise Suite is another option for a couple attending Commissioning Week. It offers a waterfront bedroom suite, kitchenette, private bath, and balcony, with striking views of the water.
It's part of the main house rather than a completely detached rental, so guests should review the listing for details about the accommodation and any other guests who may be staying on the property.
All five accommodations are part of our small waterfront micro-resort. Depending on what's booked, outdoor amenities such as the pier, hot tub, and kayaks or canoe may be shared with other Chesapeake Paradise guests.
You can compare all Chesapeake Paradise accommodations and see which arrangement might work for your family's visit.
Commissioning Week is exciting, but it also means Annapolis is busier than usual.
The Blue Angels demonstration over the Severn River is one of the most recognizable traditions associated with the week. Official plans often include arrival activities, practice flights, and the main demonstration, but schedules are subject to change.
If you're hoping to see the Blue Angels, plan your viewing location around the official flight schedule and local access restrictions. The Visit Annapolis Commissioning Week guide offers local viewing suggestions, while the Academy's schedule is the better authority for its own events.
Also keep in mind:
Allow extra time for driving and parking. Traffic near downtown, the Academy, and Navy-Marine Corps Memorial Stadium can be especially heavy on major event days.
Check bridge and roadway updates. Temporary closures may accompany Blue Angels activities.
Confirm entry requirements. Naval Academy access policies, security screening, tickets, and restrictions can change.
Review your family's event invitations. Some receptions, ceremonies, or activities are intended for specific midshipmen and their invited guests.
Make flexible meal plans. Having a kitchen at your rental can be helpful when everyone's schedule is a little different.
Staying south of Annapolis means planning for the drive rather than walking to events. We recommend checking the route and leaving additional travel time during Commissioning Week.
Commissioning Week is about the graduating midshipmen, of course, but it's also a major milestone for the families who have supported them.
When relatives arrive from different parts of the country, the time outside scheduled events often matters just as much as the ceremonies themselves.
At Chesapeake Paradise, families can prepare a meal together in the main house, spend time on the screened porch, enjoy the waterfront lawn, or sit on the pier in the evening.
Those who have some free time may enjoy kayaking or canoeing from the property, while others may be perfectly happy relaxing with a book or catching up over a cold drink.
A guest who stayed at the property with a large family described enjoying the screened porch, crabbing, and the space for different generations to enjoy themselves. That's the kind of flexibility that can be especially useful when a family is traveling for an important event.
If you have relatives joining you for a daytime celebration, please discuss those plans with us before booking. Guest counts, parking arrangements, and gatherings require advance coordination, and additional permissions or fees may apply.
If your family has an open afternoon or an extra day after graduation, there's plenty to explore on Maryland's western shore.
Historic downtown Annapolis is full of restaurants, shops, waterfront views, and opportunities to learn more about the area's maritime history. You may also want to spend time visiting local Chesapeake Bay communities and waterfront restaurants outside the city.
From Chesapeake Paradise, you can explore our recommendations for sightseeing and local attractions and waterfront restaurants and other dining options.
If you'd rather spend your downtime at the property, you don't have to plan an outing every day. There's plenty of room to enjoy the outdoors, relax by the water, or prepare a favorite family meal.
Commissioning Week includes the series of ceremonies and events surrounding the graduating class's final days at the U.S. Naval Academy. Graduation and commissioning are the culminating celebration, but the week involves other traditions, receptions, performances, and activities.
The Blue Angels have traditionally performed during Commissioning Week over the Severn River, with a graduation-related flyover also appearing on recent official schedules. Their participation, timing, and performance arrangements should always be confirmed through current official announcements.
Yes. A vacation rental can be a practical alternative to multiple hotel rooms, especially when several generations are attending. Chesapeake Paradise offers a large waterfront house, a smaller house configuration, a separate three-bedroom cottage, and private suites.
No. Chesapeake Paradise is a waterfront property in Deale, Maryland, south of Annapolis. Guests need transportation to the Academy, stadium, and downtown events. Families who prefer a waterfront vacation rental over a downtown hotel may find the tradeoff worthwhile.
Please contact us before making plans involving anyone who isn't included in your reservation. Some gatherings may be possible with advance approval, depending on the accommodation, guest count, parking arrangements, and any applicable additional charges.
Yes, it's sensible to begin looking well ahead of your visit. Commissioning Week brings many visiting families to Annapolis, and larger homes suitable for extended families may be especially important to arrange in advance. Confirm the dates of the ceremonies your family plans to attend before finalizing your reservation.
We love welcoming families to Chesapeake Paradise, and Commissioning Week is a wonderful reason to bring everyone together.
Whether your plans include the entire extended family or just a couple of relatives, our different accommodations give you several options for enjoying the Chesapeake Bay while celebrating your Naval Academy graduate.
Take a look at our waterfront accommodations near Annapolis, or contact us if you'd like help deciding which space might best suit your group.
We'd be happy to help you plan a stay that fits this special occasion.
Shawn
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