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Annapolis
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

Randell Smith loves the historic homes and waterfront views, as well as the ongoing building and growth in Annapolis, MD. With over two decades of leadership experience across numerous fields, he brings a strategic and engaging approach to vacation rental and portfolio management.

Randell’s 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. Having entered the vacation rental industry through real estate investments, he has managed a growing portfolio of long and short-term rentals for several years.

Beyond business, he’s a husband for over two decades and a father of three, Randell 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 values creating exceptional guest experiences, and believes the differential strength of Casago Annapolis lies in combining hospitality, operational efficiency, and a people-first mindset.

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Locally Owned & Operated

Table Of Contents

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!

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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!

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Osteria 177

Osteria 177

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

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Start Franchise

Book with Confidence

Start Franchise

Book with Confidence

Verified Guests and Owners

Verified Guests and Owners

Booking with Casago guarantees your stay from the minute you check in, to the second you check out. End to end reliability.

Casago Support & Security

Casago Support & Security

Never worry about support hours again with Casago's 24/7 customer support lines

Payment Protection

Payment Protection

Rent worry free with 100% cash back up to 24 hours before your stay

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.

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Quiet Waters Park

Quiet Waters Park

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

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Franchise with Casago

Start Franchise

Franchise with Casago

Verified Guests and Owners

Verified Guests and Owners

The owner's best interest is our passion and the guiding principle behind everything we do and stand for.

Team Training

Team Training

Our team members are trained to see themselves as the owner's advocate, and to make every decision from this singular mindset.

Our Guarantee

Our Guarantee

The Owner-Centric™ philosophy delivers the care, income, and transparency that you deserve.

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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
More questions

More questions?

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

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