2025 Compare Cities Rankings:
Charleston, WV vs Annapolis, MD

#44 America's Best and Worst Cities for Crime (Mid-Size Metro Areas)

#342 Best Green Cities

#1 Failure To Lunch

#2 Best Cities for Teleworking - Large Metro Areas

#3 Most Energetic Cities

#4 Most Difficult Cities to Navigate

#4 Most Irritation Prone Cities

#5 Sperlings Skincare Wrinkle Ranking

#5 Second Annual “America’s Manliest Cities” Rankings

#7 America's Best Cities for a Healthy Retirement

#8 The Most (and Least) Gender Imbalanced Cities

#12 America's Most Playful Cities

#12 Best Block Party Places

#12 2005 High Gas Prices

#15 Best US Cities for Seniors 2011

#15 Sleepless Cities 2011

#16 Wrinkle Ranking Cities Most at Risk for Skin Damage by 2040

#16 Most Secure Large Cities in the U.S.

#17 America’s Least Manly Cities

#19 Healthiest Cities

#19 Gloomiest Places in America

#20 Best Airports to Make a Connection

#22 Hypertension Hot Spots

#22 Cities on the Edge of Greatness

#25 Best Baseball Cities

#25 Most and Least Risky Places for Identity Theft

#26 The Most Single Cities

#27 America’s Manliest Sports Cities

#27 America's Top Hygge Cities

#28 Americas Manliest Cites 2011

#29 Most Competitive Private Colleges

#30 Fiscally Fit Cities Report

#32 Worst Cities for Respiratory Infections

#34 Stressful Cities 2012

#34 America’s Best (and Worst) Cities for Dating

#35 America's Most (and Least) Stressful Cities (100 Largest Metro Areas)

#36 America's Riskiest Online Cities

#37 America’s Manliest Cities

#37 Drought-Riskiest Cities

#38 Best Cities for Board Gamers

#39 Best Cities for Seniors 2005

#40 Most Romantic Cities for Boomers

#42 Best and Worst Cities for Sleep

#43 High Gas Prices - Which Cities are Hit the Hardest?

#48 Most Comfortable Summer Cities

#65 Most Popular Cities for the Holidays

#126 Best Green Cities

#179 2005 Best Places to Live

Charleston has a lot going on for being a small city. Capitol Street has great restaurants and Taylor Books, and Capitol Market is one of the best year-round farmers  More

Charleston has a lot going on for being a small city. Capitol Street has great restaurants and Taylor Books, and Capitol Market is one of the best year-round farmers  More

Charleston has a lot going on for being a small city. Capitol Street has great restaurants and Taylor Books, and Capitol Market is one of the best year-round farmers  More

Annapolis has extremely charming areas (mostly old Annapolis neighborhood's)-- Those very old area near the water have Amazing charm. You can start with downtown West  More

Well, I really would give living in Annapolis 3.5 stars. I moved here by myself several years ago. One of the highs of this place is that there are a lot of terrific  More

When we were trying to decide where in the USA to relocate to, Annapolis had enough interest that it made our list. Ultimately, we found a different city that offered  More