Family Road Trip Bucket List

We have compiled a list of our favorite road trips that you should consider taking your kids on before they grow up. Depending on where you are stationed, some of these trips should be easy to enjoy. This summer perhaps, before your PCS orders come through? Every kid should experience a classic family road trip once in their lifetime! We know there will be the “are we there yets?”, but the journey is what it is about. A road trip will allow your family to reconnect by experiencing it together. 

Pacific Coast Highway | Highway 101 runs from Seattle, Washington to San Diego, California for a total of 1,650 miles. It can be broken up into a Northern portion (Seattle to San Francisco), and a Southern portion (San Francisco to San Diego). Near Leggett, California Highway 101 splits, and you will take Highway 1 if you wish to continue right along the scenic coastline. The coastal cliff views, and bridge spans may be the most picturesque road that your kids will experience. 

DON’T MISS: 40 miles of sand dunes along the coast at the Oregon Dunes National Recreation Area. Eureka, California, a Victorian-era town. The Redwood trees near Leggett, California including the Chandelier Tree that you can drive through. The Mystery Spot near Santa Cruz, California that defies gravity. The iconic Hearst Castle overlooking the Pacific in San Simeon, California.

The Oregon Trail | 3,100 miles from Cape Cod, Massachusetts to Portland, Oregon. The Oregon Trail took early pioneers on a Northerly route across North America. The route passes by several natural wonders of the world including Niagara Falls, Mt. Rushmore, and Yellowstone Park. 

DON’T MISS: The history and museums of Rochester, New York including the Toy Hall of Fame. The Baseball Hall of Fame in Cooperstown, New York. The Rock & Roll Hall of Fame in Cleveland, Ohio. If travelling in August, stop at the internationally-acclaimed Iowa State Fair in Des Moines. Finish the trip by picking your own cherries, berries, and apples along the Fruit Loop near Portland, Oregon.  

Historic Route 66 | “Get your kicks…” The iconic Route 66 no longer exists in its entirety, but runs from Chicago, Illinois to Santa Monica, California. The classic road trip travels across the American Midwest, Great Plains, and the Southwest. There are fun attractions along the route, and you can begin and end your trip with a ferris wheel ride!

DON’T MISS: The Big Blue Whale of Catoosa near Tulsa Oklahoma is a kitschy roadside attraction. Bring your own can of spray paint for the cars at Cadillac Ranch in Amarillo, Texas. Ride the ferris wheel at the Santa Monica pier. 

East Coast | This should be broken up in smaller chunks so you can take in all the history and big city stops along I-95. This route is loaded with historical landmarks, museums, and parks that kids should experience. Plus Boston, New York, Philadelphia, Baltimore, and Washington DC, which are full trips themselves!

DON’T MISS: The mansions in Newport, Rhode Island. A Broadway show in NYC! The Rocky Steps in Philadelphia, Pennsylvania. A Ghost Tour in Savannah, Georgia. A beach day in Virginia Beach, Virginia. 

Florida Keys | The Overseas Highway is 160 miles across the water from Miami to Key West. This is the shortest trip on our list and can be done in 1 day. Of course, longer stops can be taken along the way.

DON’T MISS: See alligators and manatees at Everglades National Park. The Turtle Hospital in Marathon, Florida. The six-toed cats at the Ernest Hemingway House in Key West. 

We hope one of these trips, or a portion of one, will be a fun-filled, and memorable time for your family. When you are facing your next PCS move, contact one of our Military Relocation Specialists for assistance.