Always wanted to go on a road trip, but not sure about best time to go? We’ve got you covered with 13 special times in your life that are perfectly celebrated with a road trip, along with some of our suggestions on where to go. Maybe you’ll take a road trip every year of your life, or maybe you’ll take one and that’ll be enough, but not having time will no longer be a valid excuse!
- High school graduation/gap year
Ready to go explore the world and become your own person? Before tackling your next endeavor, head out with some friends and see what the world has to offer! There is no education quite like experience, and you’ll definitely have plenty of those while taking a post-high school road trip.
Our suggestion for celebrating the end of high school (and the beginning of the rest of your life)? The Pacific Coast Highway. Seeing the open road hugging the ever-changing coast gives that special, exhilarating feeling of freedom, and you'll get to cross some experiences off your bucket list as you cruise through cities like San Diego, Los Angeles, and San Francisco.
- College spring breaks
Spring break may only be a week long, but you can squeeze a lot into a little for an inexpensive, exciting respite from the grind of higher education. Camp for cheap or cram as many people as you can into hotels to keep the cost down, and drive out to your destination in lieu of booking an expensive plane ticket.
If you want the classic spring break experience, drive down to a city on the Florida coast, like Daytona Beach. The trip to your final destination will be just as memorable as the beach itself... maybe even more so since your time in Daytona will likely be spent lazing out on the beach and consuming copious amounts of alcohol. You're only young once!
- Post-college graduation/pre-career
You’ve finished college and are jobless and avoiding the real world, so why not make your job tramping ribbons of the highway? With the wind at your back, and that undying undergraduate optimism still running through your veins, college graduation is the perfect block of time to drive around the country.
By this age, you'll definitely be able to fully appreciate the significance of our National Parks. Zion is a rare beauty, featuring breathtaking hikes and unforgettable red rocks landscapes. It's also in Utah, which is home to four other incredible National Parks, all totally unique and each more stunning than the last.
- While you’re single
While you're single and ready to mingle, why not go out and see who and what is out there? Being in a relationship is great, but you have plenty of time for that later on, so why not buckle up before you get buckled down and live free and easy?
Take full advantage of the single life with a trip to Vegas. That's not to say that you have to indulge in Sin City's seedier activities, but Vegas can truly be enjoyed when you're totally free to let loose and see where the night takes you... without having to worry about anything holding you back!
- First vacation with a significant other
Once you find someone willing to put up with your wily personality and your incurable travel bug, grab your keys and map and head for the horizon. A road trip is a great test of your relationship! Nothing brings people together like being stuck in close quarters for hours at a time, and you'll make some lasting memories.
For a super romantic first vacation, take a road trip through Big Sur. It has beautiful scenery, misty beaches, cute small towns, cozy B&Bs, and fun little shops and roadside attractions that are an adventure to explore.
Big Sur, California, United States
- National Holidays
While you may not be able to go extremely far distances, holidays not only offer time off work but are usually accompanied by some pretty fun festivities. Fireworks for the Fourth, lights in winter, parades for St. Patrick's, and food for Thanksgiving... every holiday has its special traditions, and towns across the country love to celebrate them in their own unique ways.
Washington, D.C. has something going on for most holidays. Cherry blossoms in the spring, tons of events during Independence Day, the turkey pardoning for Thanksgiving, the National Christmas Tree during winter... the list goes on and on. Besides, every American should visit our nation's capital at least once in their life, right?
You’ve finally tied the knot, and what better way to spend your honeymoon than throwing caution to the wind and following your every whim? Honeymoons on the road will allow you to see a lot and spend a ton of time together.
The Blue Ride Parkway is the perfect honeymoon road trip. It connects two National Parks (Shenandoah and the Great Smoky Mountains) and offers great views and tons of Southern charm in between. Whether you're an outdoorsy couple or you'd rather spend your days soaking up culture or enjoying delicious food, there's something for everyone along the route.
- When the family is ready
Many know the feeling of settling down a little too much for your liking once you start a family, but once you kids are old enough, you can drag them across the country on a big road trip! It's a great bonding experience for everyone, and even though your children might not love the idea of being stuck in a car with their parents for days on end at first, they'll appreciate the fun you'll get to have along the way... eventually.
It doesn't get any more classic "family road trip" than Route 66. There are tons of kid-friendly stops that adults can enjoy along the way, and your family will be getting a little history lesson along the way as well. Plus, it's a great way to really see America, since it crosses the heart of the country.
Getting older doesn’t mean you have to grow up! Celebrate birthdays by getting behind the wheel and checking out a place you’ve always wanted to see but have never gotten to visit. Trips are way better gifts than new socks!
If you're looking for a great spot to celebrate, look into a road trip to Nashville. Enjoy a Bushwacker, killer live music, and amazing food (hot chicken, anyone?) in Music City. You don't have to be a country music fan or history buff to enjoy the fun nightlife here, but it certainly helps... and if you're looking to get off Broadway for a day, visit the nearby town of Franklin.
Looking to rekindle the fire you felt when you first fell in love? Discovering a new place can help you remember why you fell in love with the old ball in chain in the first place. Make your next anniversary a trip down memory lane by taking a trip down to one of your old favorite locations.
Or, if you want to celebrate with an adventure to a new place, head to the Poconos. It's been a romantic retreat for couples for decades... and if you and your partner are looking to shake things up, Cove Haven Resort has a suite that features a hot tub shaped like a champagne glass. There's nothing like a kitschy adventure to bond over!
Haven’t seen your pals in a while? Need a girls vacation? Trying to get back together with your high school or college friends? Why not invite them all on a super rad road trip to reconnect, remember the good old days, and create new memories to last a lifetime!
Renting a cabin or staying at a resort in the Rockies is a great way to reconnect. Whether you want to cozy up in a cottage and just reminisce, or you'd rather get out and explore the little towns, awesome hikes, and cool attractions here, it's perfect for a get-together with old friends!
You’ve worked hard for a long time, and you deserve a fun retirement! What better way to spend your life savings than by going around to wherever you feel like, whenever you feel like it? Retirees all need a hobby to stay sharp and entertained, and nothing will keep you on your toes quite like the adventure of travel.
Once you're retired, you have the freedom to fly south for the winter in search of warmer climates. Key West is always a blast, and it's the best way to make the most of your retirement! Spend your days drinking fruity, rum-laced cocktails on a sunny patio instead of behind a desk in an office.
- Bucket list twilight tour
Getting a little older but still have a few sights left to see? Don’t waste any time in getting to that picturesque beach spot you’ve always dreamed of, summiting that mountain you always craved, or just chasing sunsets across the country while on a road trip to top all road trips.
Me, personally? I'd love to sit on a rocking chair on a porch in Cape Cod and just... relax. The mild weather, peaceful views, and slow, small-town life make the perfect place to reflect on a life full of adventure and travel.
Of course, there's no bad time to take a road trip! But, some people need a little push to actually hit the road, and if you start planning for a road trip to celebrate milestone events in your life now, you'll be ready for adventure!
Roadtrippers helps you find the most epic destinations and detours—from roadside attractions to natural wonders and beyond.