The seal has the elements of the city flag adopted in January 1965, but some details have changed over the years.
The left rendering approximates the original seal, and the right rendering is based on a physical flag obtained from the the city government in early June 2020 (age unknown).
Annapolis's first official flag, adopted in January 1965, is styled after the personal royal badge of Queen Anne after whom the city was named. Resembling the floral badge of Great Britain, a crown hovers over a thistle (representing Scotland) and a rose (representing England), growing from a single stalk to portray their union. The motto Vixi liber et moriar means "I have lived free and will die so".
— Quotation from the Annapolis Evening Capital, January 12, 1965:
Image caption on page 1 of newspaper: "City's First Flag ... The emblem which the flag depicts was the personal badge of Queen Anne of England, for whom Annapolis was named, which she wore to symbolize the union between England--represented by the rose on the right--and Scotland--represented by the thistle on the left. The red rose is of the House of Lancaster and the white rose of the House of York. The hovering crown further emphasizes unity. At the flag's base is the motto, "Vixi liber et moriar" ("I have lived free and will die so").
This image shows a flag, a coat of arms, a seal or some other official insignia. The use of such symbols is restricted in many countries. These restrictions are independent of the copyright status.
अनुमतिदानम्
For original flag design:
Styled after a 300+ year old design for Queen Anne (1965 design doesn't meet threshold of originality warranting copyright protection)
Published in U.S. without apparent copyright notice at least as early as its official adoption in January 1965.
Note that it may still be copyrighted in jurisdictions that do not apply the rule of the shorter term for US works (depending on the date of the author's death), such as Canada (50 p.m.a.), Mainland China (50 p.m.a., not Hong Kong or Macao), Germany (70 p.m.a.), Mexico (100 p.m.a.), Switzerland (70 p.m.a.), and other countries with individual treaties.