Shuttle Services

Chesapeake Charters: Your Transportation Solution in Annapolis, Maryland

Chesapeake Charters is your headquarters for charter buses in Annapolis. We feature transportation for schools, church outings, weddings, special events, and much more. We were the official transportation of the Polar Bear Plunge in 2011 for Special Olympics, which gave children a chance to compete in a type of winter sport they would not ordinarily get to do.


Here are the primary services we offer:

  • Wedding Transportation
  • Shuttle Services
  • School Field Trips
  • DC Tours
  • Tours to Atlantic City, Baltimore, and Annapolis
  • Transportation for all events and occasions

In addition to the above basic services, we also feature a 44-passenger school bus for school outings, as well as high class Motor Coach buses which will take you anywhere in the Annapolis area in style. We pride ourselves in being the best Annapolis charter buses headquarters in the Metro D.C., Maryland, and Virginia areas.


We have several special amenities and servies on our buses which many of our competitors do not have including:

  • Restroom Facilities
  • Overhead Storage
  • Public Address System
  • Video Equipment (for security)
  • Eating and Drinking Accomodations
  • Plush, Reclining Seats/Foot Rests
  • Climate Control
  • Luggage Bay Storage areas
  • and more


We care about you, our customers and we want you to sit back and enjoy the drive through D.C., Baltimore, Annapolis, or anywhere you want to go. If you are visiting Washington D.C., ask about our special tours. They are professionally done and feature all of the important landmarks and sites of our nation's capitol. We promise that you will enjoy your trip to D.C. anytime you choose to use Chesapeake Charters as your primary transportation. You can travel in comfort and style and visit with your guests and leave the driving to us.


Our founder, John J. Lonergan, Jr. established Chesapeake Charter, Inc. back in 1976, beginning with only one school bus which provided transportation to the Anne Arundel County Public Schools. Now we transport people all over Virginia, Washington D.C., and Maryland, as well as the surrounding areas. We now proudly boast a fleet of 6 Motor Coaches and 36 school buses to transport kids and adults alike to area events.


Over the years since our humble beginnings in 1976, Chesapeake Charters has grown and we have earned a reputation for excellence with our clients. They have come to expect professional and courteous service and that is what we give them, time after time.


If you are planning to come to the D.C. area, Baltimore, Virginia, or anywhere in the vicinity and you need charter buses in Annapolis, contact us. You'll see a map on this page which will take you to us easily from any of the three main locations you are coming from. We want to be your go-to headquarters for all of your transportation needs and events. So whether you need school buses for your school trips, wedding transportation, or other, let us know how we can help. Then just sit back and let us do the driving. That is what we do best!

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