This is a big year for America. The country turns 250 years old in 2026 and its favorite road, historic Route 66, is turning 100. That means a whole century of memories for amazing family travel road trips from Chicago to California and back.
The route’s official start is in Chicago, where it then travels through eight different states before ending on the Pacific Coast in the beach city of Santa Monica. This beach town isn’t just the end of the road (there’s actually a Santa Monica 66 End of the Trail sign marking the end of the route, the perfect place for a photo finish), it’s also quintessential California. The surf vibe is in full swing, there is plenty to see and do, and the sun is shining almost every day.
You’ll want your road trip to culminate with a trip to Santa Monica Pier, where you can enjoy some souvenir shopping and plenty of good eats, along with carnival games and rides on the waterfront — the 1939 carousel is a nostalgic ride you won’t want to miss. Take a walk along the boardwalk, dip your toes in the sand or build sandcastles with the kids at Santa Monica State Beach — and, of course, watch surfers catch some waves while you’re there.
Just a short walk from the pier is Third Street Promenade, a pedestrian-only outdoor shopping area filled with popular chains and charming boutiques, along with plenty of places to grab a refreshing drink or a bite to eat.
There are plenty of options in the city when it comes to accommodations, from 5-star Shutters on the Beach to the affordable Days Inn by Wyndham Santa Monica. But one of the best things about Route 66 ending in Santa Monica is it drops you off in the perfect location to experience all the rest of what Southern California offers, like Malibu, Huntington Beach and Hollywood. Even San Diego and Santa Barbara are just a few hours’ drive away.
Read This Next
Plan A Festival Season Vacay with Teens
Destinations / North America
Mar 13, 2026#WhereverFamily
Insta FeedHotels
Mar 10, 2026This Hotel is the Perfect Base for Families in Tokyo
For years, whenever I asked my children where they wanted to go next, the answer was always the same. “Take us to Japan,” they said. When we finally made it, I put a lot of thought into where to stay.
Sponsored Content
Best of Both Worlds
Enjoy the best of both worlds when you fly with TAP Air Portugal thanks to the Portugal Stopover program. With the program, TAP passengers, whether traveling for business, leisure or both, can stop in Portugal for up to 10 days at no additional airfare on the way to their final destination. What does this mean for travelers wishing to explore by both land and sea? It means after flying to Portugal with TAP and experiencing the country in an entirely new way, travelers can then embark on scenic river and ocean cruises from Portugal’s port cities, or fly with TAP to another European destination.
Hotels
Mar 10, 2026The Ritz-Carlton Waikiki Beach Launches Signature Experiences Rooted in Culture, Community
The Ritz-Carlton Residences, Waikiki Beach invites family travelers to experience its first-ever collection of immersive signature experiences, offering a redefined look at O’ahu. These experiences incorporate the hotel’s core pillars and reflect its commitment to cultural authenticity, craftsmanship and community.
Hotels
Mar 9, 2026Capitol Hill Hotel Debuts America 250 Experiences for Travelers
Hyatt Regency Washington on Capitol Hill invites family travelers to celebrate both America’s 250th anniversary and the hotel’s 50th anniversary this summer. The hotel sits just 1,287 steps from the U.S. Capitol Building, making for the perfect homebase to experience all things America’s anniversary. To top things off, the hotel offers two special promotions to help families make the most of their visit to the nation’s capital.
Sponsored Content
TAP Air Portugal: A Milestone Year
From small airline to global success, TAP Air Portugal turns 80 and better than ever.
Airlines
Mar 6, 2026Icelandair’s Long Weekend Getaways Are a Great Way to Explore
Icelandair is well-known for its stopover program, which allows passengers to stay in Iceland for a few days at no extra charge. It’s a great way for families to see a new place and explore a new country on their way to and from Europe. When my family travels, we enjoy spending a couple days exploring Reykjavik and Iceland’s natural beauty as part of our trip. Iceland has become one of my family’s favorite destinations. We always find something new to do, no matter how many times we visit.
ShareThis