Getting to Annapolis

  • Baltimore Washington International Airport (BWI): BWI airport is a easy 30 minute drive from Annapolis, MD and the most convenient airport to the hotels and the festivities! BWI is also a Southwest hub with plenty of options from large and small cities alike. 
  • Ronald Reagan Washington National Airport (DCA): National airport (or "DCA" as the kids call it) is located across the Potomac river from DC and is a 40 minute drive from Annapolis - without traffic. During weekday rush hours (3-7pm), expect to tack on another 20-45 minutes.  For those looking to explore DC on Sunday, this would be convenient choice from which to depart.
  • Washington Dulles International Airport (IAD): Dulles is....a pain. Located on the opposite side of DC as Annapolis, Dulles is a 65-75 minute drive with no traffic. During weekday rush hours (3-7pm), or any other random time, expect to tack on another 30-90 minutes to brave the DC beltway.

When in Annapolis

  • Friday night: There will be a trolly or bus of some sort to take you from the hotels to the Paca House and back, or if you'd enjoy a stroll, it is a mile walk from the Westin or a 0.8 mile walk from the O'Callaghan.  
  • Saturday: There will be transportation from the Annapolis hotels to Severna Park.  We do not suggest walking this one.  
  • All other times: We recommend 3 main modes of transportation when exploring Annapolis
    • Taxis / Uber: The hotels can help you get a cab or Annapolis has Uber!  
    • Annapolis Circulator Trolley: Thanks to the generous tax payers of Annapolis, a complimentary trolley is available from Westin and the O'Callaghan to points downtown. The trolley runs every 10 minutes and is available from: 
      • Sunday - Thursday: 6:30am - midnight
      • Friday - Saturday: 6:30am - 2:30am (yes, that's AM! Party on Annapolis)
    • Walking: Travel like it's 1790. Downtown Annapolis is a 10-15 minute walk from O'Callaghan's  and a 15-20 minute walk from the Westin. For those traveling back and forth from the hotels, O'Callaghan's and the Westin are 0.2 miles apart or 5 minutes.
The free trolley!  

The free trolley!  

Or you can kick it old school and walk. 

Or you can kick it old school and walk.