Best Long Weekend Road Trips from 7 Major Cities

Travel is a little different these days as many of us are turning to good old fashioned road trips instead of flights to far away places. You can learn so much as you pass through new towns and experience sights and sounds on the road. But what if you don’t have time for a full-on holiday? Try a weekend road trip! You can cover a lot of ground in a few days if you plan it correctly. Save a few bucks to enjoy activities and such at your destination by booking your rental car, lodging and more with Rakuten Travel & Vacations. Below, I’ve rounded up a few of the best long weekend road trips from some major cities.

Road trips from Chicago

You have a couple options here. First, you could pack up your things and head for South Haven on the other side of lake Michigan, which is only two hours away. It’ll offer a nice escape from city life in a relatively sleepy beach town. Second, you can head north to Milwaukee for a nice escape in a highly underrated midwestern city. There’s plenty to do outdoors and you can stop at the Mars cheese castle on your way back. Who wouldn’t want to visit a castle filled with cheese?

Road trips from Dallas

If you have at least 4 days and want to hit the beach, the city of Kemah is around 4 hours away from the city center of Dallas, and it has plenty to do for the whole family. If you’re just looking for a change of pace with all the flavors of city life, Austin is an hour closer. If you’re going to visit Austin, Franklin Barbecue is an obvious choice, but I suggest La Barbecue as a top spot for some of the best barbecue in Texas and way less of a wait.

Road trips from New York City

Get out of the city and head north about an hour and a half to Storm King Art Center. It’s the perfect place for social distancing as you can explore more than 500 acres on foot. There are numerous massive sculptures and some natural art that’s quite literally carved into the countryside. My favorite piece was the giant “Mermaid” by Roy Lichtenstein.

Road trips from Los Angeles

Temecula is a few hours outside Los Angeles and offers an easy-going escape from the urban sprawl of LA. It’s known as a wine town with wineries and farms scattered throughout the mountains, but you should also check out the olive oil while you’re there. There are plenty of places to sample both wine and olive oil, so plan your route accordingly and make sure you have a designated driver.


Road trips from San Francisco

Big Sur was our favorite place to take a road trip from San Francisco on long weekends as it offered an incredible escape from city life. There’s something magical about California Highway 1, and the drive down to Big Sur is just as breathtaking as the destination itself. Andrew Molera State Park is my top choice if you’re into camping; however, parts of the park are closed from time to time. It’s first-come, first-served, so you need to get there early with cash in hand to reserve a campground spot, but you don’t have to stay overnight to enjoy all this park has to offer. If you continue hiking beyond the campground, there’s a trail that puts you straight onto the beach with miles of open and secluded coastline. 

Road trips from Houston

Galvelston Island is a short ride away from Houston and offers a little beach escape if you need a change of pace from city life. The Historic Pier is a cool spot for grabbing something to eat and the best views of the ocean. If you’re looking for a truly peaceful getaway, the Galveston Island State Park has camping, hiking and more, all on the gulf coast.

Road trips from Atlanta

If you have an extra long weekend, I recommend heading out to the Golden Isles in Georgia. It’s around 5 hours depending on traffic, but the trip is more than worth it to spend a little time on St. Simons Island, Little St. Simon’s Island, or Jekyll Island. If you can only pick one destination, I recommend St. Simons Island where you can visit St. Simons Lighthouse museum, which is a working lighthouse built in 1872. There’s also plenty of options for activities including fishing, biking, golfing, and more.

Take some time to prepare for your excursion with this handy list of road trip essentials for the entire family. Didn’t see your city on the list? Search Rakuten Travel & Vacations for packages or coupons for destinations or experiences in your neck of the woods. If you’re not a member, spend a few minutes and sign up today.

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