Road Trips / Eastern Seaboard / Villages of the Chesapeake


You are purchasing the Villages of the Chesapeake Christopher Travel road trip itinerary.

The eastern shore of Maryland is dotted with quaint coastal villages where for generations people have sought refuge from the hustle and bustle of daily life. This gentle road trip is filled with plenty of time to relax, sail, fish, cycle and shop. From country inns and B&Bs to world class resorts there are some amazing places to stop and settle in as you make your way along the Chesapeake over to the ocean.

Please note that pre-planned itinerary purchases are only for the informational trip itinerary. Our overnight stops are planned for locations with a variety of accommodations for you to book on your own.

Villages of the Chesapeake Road Trip by the Numbers:

  • 8 days / 7 nights
  • Total driving time: Approximately 3 hrs. and 30 min. (time estimate is without traffic)
  • Longest driving time for any one travel day: Approximately 1 hr. (time estimate is without traffic)

This is planned as a local drive so total estimated drive time starts in Annapolis and ends in Ocean City

Villages of the Chesapeake Destinations & Highlights

  • Annapolis
  • St. Michaels
  • Easton
  • Oxford
  • Cambridge
  • Salisbury
  • Ocean City

All Pre-Planned Itineraries Include:

  • Reasonable drive times balanced with fun activities and stops
  • One time payment of $5 for your trip itinerary
  • Your pre-planned trip is ready to go!
  • Day by day planning download for one user of our itinerary phone application
  • Recommendations for notable places to eat, when available
  • Ideas for activities and stops along the way
  • Routes planned for you to select and book accommodations on your own
  • Purchase additional add-on options for your journey (see below)

After purchase you will receive a link to download your itinerary app. Those who pay for the Semi-Custom option will also receive a link to make an appointment for your initial consultation. Please allow 24 hours and check your junk mail if you have not received your app instructions. If you have any questions please call us: 202-601-0119 or email

Upgrades to Semi-Custom and Custom itineraries are also available.

For Semi-Custom and Custom road trip itineraries we include suggestions for multiple different property types:

  • Unique and Immersive properties are usually higher end (but not always).
  • Family friendly and pet friendly are typically more moderately priced.
  • Loyalty program properties may also be available in some locations if you’d like to earn or redeem points.

Accommodation options for Semi-Custom and Custom itineraries will be discussed during our phone consultation -- you will receive a separate invoice and payment authorization for any accommodations booked on your behalf by Christopher Travel.


  • Christopher Travel LLC Terms & Conditions are attached to all itineraries (both the web view and within the phone application) and available online at
  • Itineraries are informational in nature and the purchaser is responsible for routing & navigation to implement the informational itinerary in a safe and legal manner while road, weather, border status, and travel conditions permit.
  • Purchaser is responsible for contacting vendors and providers of all included itinerary items for operating hours & dates, special events, instructions, and anything else that may impact the implementation of the itinerary.
  • The Christopher Travel team regularly reviews and updates itinerary information, please contact us if we need to make any additional updates, your feedback is appreciated!
  • Content is produced by Christopher Travel LLC. © 2020 Christopher Travel LLC. All rights reserved.

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