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Welcome to

Annapolis

Located on the banks of the Severn River and Chesapeake Bay, Maryland’s capital city invites guests to explore its historic architecture, fresh seafood, brick-lined streets, and vibrant waterfront. This year-round coastal destination offers colonial charm paired with nautical adventures for visitors of all ages.

Largely considered part of the Baltimore-Washington Metro Area, Annapolis is just a 45-minute drive to Washington, D.C. or Baltimore. This makes it a terrific spot to cast off for exploring the eastern seaboard, offering over 500 miles of shoreline in Anne Arundel County, along with scenic rivers, creeks, and trails.

Known as the “Sailing Capital of the World,” Annapolis, Maryland is deeply rooted in its historic maritime heritage and is home to the US Naval Academy. Families and groups frequently visit midshipmen at the Naval Academy, while Commissioning Week each May is a time-honored tradition filled with celebration and fanfare.

Along with its seafaring legacy, the academic and historic atmosphere in Annapolis extends to the campus of St. John’s College. History buffs can appreciate the State House in Annapolis as the oldest in continuous legislative use in the nation, or visit the home of William Paca, one of Maryland’s signers of the Declaration of Independence.

With its mix of maritime culture, history, and year-round appeal, Annapolis is a consistently attractive getaway for families and history enthusiasts alike. Plan a visit to discover why this historic seaport remains a favorite treasure of the Chesapeake Bay.

Locally Owned & Operated

Annapolis

Annapolis

Casago Franchise Owner

The Casago Annapolis team is made up of dedicated professionals with vast experience in leadership and property care, ensuring the best possible service for guests and homeowners alike. This value of creating exceptional guest experiences highlights the differential strength of Casago Annapolis by combining hospitality, operational efficiency, and a people-first mindset.

Meet the Casago Annapolis Team!

With over two decades of leadership experience across numerous fields, Randell Smith brings a strategic and engaging approach to vacation rental and portfolio management. His background encompasses honorable service in the U.S. Army Medical Service Corps, followed by earning his Juris Doctorate in 2013. His leadership experience spans from legal and financial services to insurance defense and entrepreneurship.

Beyond business, Randell has been a husband for over two decades and a father of three who is active in his community and family life. He is an active member of the Anne Arundel County Association of Realtors (AACAR), Vacation Rental Management Association (VRMA), National Association of Property Managers (NARPM), National Association of Realtors (NAR), Member of the Virginia Chamber of Commerce, and Member of the National Notary Association.

Randell is joined by Danette Fastner, Local Operations Manager, as well as Property Crew Leaders Lucy Fastner and Jennifer Gaines.

As Local Operations Manager since 2022, Danette strives for perfection and above all solidifying a great relationship with homeowners. With nearly 1½ decades in the property management industry, Danette perfected her skills first as the owner of a cleaning company and then as Property Manager before stepping into her current role. She is proudly the mother of 6 and Lala of 3, along with two dogs and a pair of goats.

Property Crew Leaders Lucy Fastner and Jennifer Gaines joined the team in 2023 and 2022 respectively. Lucy, as a new mom, and Jenn, a grandmother and mother of three, are masters of multitasking with a careful eye for detail.

Prior to becoming a full-time Property Crew Leader, Lucy had been working in property care since 2018 as an essential energetic go-to assistant. Her bubbly and talkative personality continues to delight homeowners and she is sure to treat every vacation rental with the same care she’d give her own home.

Equally ready to jump in to ensure homeowner confidence and guest satisfaction, Jenn joined the property management team in Annapolis after having lived and worked in other states for over two decades. Her meticulous attention to detail translates into welcoming stays for guests.

Our entire Casago Annapolis team works at providing five-star hospitality to guests, while preserving the trust of our homeowners.


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Locally Owned & Operated

Things to do

What you need to know

Known worldwide as the Sailing Capital of the United States, Annapolis is home to military and American history, historic homes, and museums. Add the fresh seafood, and it becomes a vacation hotspot.

Recommended by locals

Annapolis is jam-packed with attractions, like the United States Naval Academy and the Colonial Annapolis Historic District. From history to sailing and scrumptious seafood, there's something for everyone!

Restaurants

What you need to know

Seafood is king in Annapolis! The Chesapeake Bay means you'll find boat-to-table fresh seafood throughout the city. From beach shacks to fine dining, there's an eatery waiting for you to discover.

Recommended by locals

Waterfront fine dining awaits at Carrol's Creek Cafe, while some of Maryland's best crab cakes are at Boatyard Bar & Grill. From Italian cuisine to wine cafes, the choices are limitless!

Osteria 177

Osteria 177

Downtown Annapolis is known for its historic charm and lively food scene. One...

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Sightseeing

What you need to know

Annapolis is known for its sailing, so take a cruise or catch a race in the Chesapeake Bay. American history, museums, art galleries, and parks make sightseeing enjoyable and rewarding.

Recommended by locals

Book a sunset voyage with Schooner Woodwind Sailing Cruises or tour the U.S. Naval Academy. Museums, restaurants, and historic homes in the Colonial Annapolis Historic District will appeal to all ages.

Quiet Waters Park

Quiet Waters Park

Quiet Waters Park is a 340-acre outdoor wonderland featuring playgrounds, paved...

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Frequently Asked Questions

There are three international airports providing easy access to Annapolis: Baltimore-Washington International Thurgood Marshall Airport (BWI), Ronald Reagan Washington National Airport (DCA), and Washington Dulles International Airport (IAD). The BWI Thurgood Marshall Airport is located in Anne Arundel County, Maryland and just about 20 miles from Annapolis.

Annapolis is a year-round coastal destination, but the city truly comes alive from April through October, when mild temperatures and waterfront breezes create perfect conditions for sailing, dining, and exploring its historic streets.

Spring welcomes visitors with cherry blossoms along the shoreline, vibrant boating activity, and the start of festival season.

Summer is peak travel time, drawing families, Mid-Atlantic vacationers, and boating enthusiasts to the Chesapeake Bay for sailing charters, crab feasts, and lively harbor events.

Fall is considered one of the best-kept secrets in Annapolis, offering warm days, crisp evenings, and stunning waterfront foliage—ideal for romantic getaways, maritime experiences, and the energetic atmosphere surrounding the U.S. Naval Academy’s football season.

In winter, the city maintains strong appeal with holiday lights, cozy waterfront restaurants, and historic tours, giving travelers a charming off-season experience.

High: March – September
Low: January-February; October – December

Annapolis is very family-friendly, with several attractions near the City Dock and a high walkability factor throughout the historic downtown and some of the surrounding older neighborhoods.

Street parking, metered parking, and parking garages are available in and around downtown, though stay alert to city events (especially at the Naval Academy) that can increase traffic.

Many of the biggest events in Annapolis center around the area’s rich maritime history as well as those at the U.S. Naval Academy:

  • Spring Sailboat Show (April)
  • United States Sailboat Show & U.S. Powerboat Show (October)
  • Maryland Seafood Festival (September) & Annual Crab Feast (August)
  • Naval Academy events
    • Commissioning Week (May) at the U.S. Naval Academy
    • I-day (Induction Day – June)
    • Army-Navy Football games
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More questions?

Feel free to send us an email with any and all questions you might have regarding the start of a Casago Franchise!

We'd love to help answer your questions!