Colonial America

  • Maryland + 5 more
  • Self Drive Ideas
  • 10 Days
from  £880pp
Book today


Explore the history of the Civil War, hike one of the many trails along Skyline Drive in Shenandoah National Park, walk the boardwalk of Virginia Beach, shop and dine in Baltimore’s Inner Harbor, discover the Liberty Bell in Philadelphia.

A Free Personalised Road Book is included as standard with our Self Drive itineraries. 


Please note: – This is a suggested itinerary only and is intended to give an overview of what is possible. All of our holiday itineraries are fully customisable and can be tailor-made to suit your own individual requirements.  If you would like to start in a different destination, use specific hotel accommodation, include an extra night here, a side-trip there and/or include tickets to an event please let your Discover North America travel specialist know. They’ll also book you the best value flights to ensure a seamless holiday experience.


Book today


Day 1 Washington D.C.

Arrive in Washington, D.C. and pick up your rental car at the airport, then proceed to your hotel.

Day 2 Washington D.C.

A full day to explore Washington, D.C. Start by strolling along the Mall. Here you will find some of the most important monuments and have the opportunity to lose yourself in some of the world’s most inspired museums. After lunch why not journey across the Potomac to nearby Alexandria or perhaps you would prefer to rent a bicycle and continue your exploration of the city. This evening we suggest a visit to the lively Georgetown area of the city where some of the best chefs vie for your attention.

Day 3 Washington D.C. – Gettysburg (90mi/150km)

Leave the seat of government behind today as you travel to the fascinating Civil War battlefield of Gettysburg. There are many excellent self-guided interpretative trails you can follow that will give you an understanding of this formative period in U.S. history.

Day 4 Gettysburg – Shenandoah (150mi/250km)

Today there is time for further exploration of Gettysburg before you head west to visit Luray Caverns, one of the most beautiful caves in the world. Then enter Shenandoah National Park, a haven for plants, wildlife, and people alike.

Day 5 Shenandoah – Skyline Drive – Chalottesville – Colonial Williamsburg (172mi/275km)

Drive south and enjoy the natural wonders along each mile of Skyline Drive, one of America’s most scenic routes. You can see the peaks of the Blue Ridge Mountains which have a distinctly bluish cast, especially in summer. Then continue to Charlottesville and visit Monticello, the home of Thomas Jefferson designed and built on a glorious mountaintop. Continue to Richmond, Virginia’s capital, rising high above the sparkling James River, before travelling along the scenic road by the James River Plantations to Williamsburg, where restoration and preservation have turned back the clock 200 years.

Day 6 Colonial Williamsburg – Norfolk – Virginia Beach (63mi/101km)

Visit Colonial Williamsburg, then see the earliest permanent English settlement in North America at Jamestown. Continue to the Yorktown Battlefield, where Washington’s decisive victory over General Cornwall’s forces turned the colonists’ dream of a new nation into reality. Continue through Norfolk, Virginia’s premier port city, to Virginia Beach, with 30 miles of sandy seashore and a 2-mile-long boardwalk. Time to relax this evening and dip your toes in the ocean.

Day 7 Virginia Beach

Today spend your time in the city that is listed in the Guinness Book of Records as having the longest
pleasure beach in the world. To continue with this record breaking tradition, the city itself is located at the southern end of the Chesapeake Bay Bridge-Tunnel, the longest bridge-tunnel complex in the world.

Day 8 Virginia Beach – Eastern Shore – Annapolis – Baltimore (248mi/397km)

Drive north across the Chesapeake Bay Bridge-Tunnel to the tranquil Eastern Shore. Cross into Maryland and continue on to Annapolis, home to the U.S. Naval Academy. See the State House and visit the Academy before continuing to Baltimore. This evening, stroll along the magnificently rebuilt Inner Harbor and enjoy a typical dish of the region in one of the many restaurants.

Day 9 Baltimore – Philadelphia (100mi/160km)

This morning you are bound for the City of Brotherly Love – Philadelphia. This historic city is home to both Independence Hall and the Liberty Bell. Philadelphia also boasts a world class art museum as well as superb shopping and dining.

Day 10 Philadelphia – Washington, D.C. (140mi/250km)

Drive back to Washington, D.C. and return your car at the airport before your departure flight.