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The 5 Most Romantic American Road Trips for Couples in 2023

  • February Events
  • Renee Martin
  • 6 minutes

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February is here, and that means it’s time for Valentine’s Day. If you find romantic candlelight dinners and carriage rides cliched, you might want to consider a road trip. The old adage says, ‘Couples that drive together stay together (Nah, it’s not old. We just made it up ?). A romantic road trip is a great option. What better way to bring two people together than planning and exploring the romantic side of America together.

We’ve got you covered with routes and even a romantic road trip playlist:

If you are seriously considering planning and taking on a romantic Valentine’s Day road trip, you should consider these five most romantic road trip routes. Pro tip: Don’t let parking hassles be a worry, and get your hands on guaranteed parking spots. Grab your maps out, and let’s dive straight into these romantic road trip routes now!

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1. Chicago to Santa Monica

road trip for couples

Starting the trip by sharing a slice of deep-dish pizza and visiting the many roadside romantic diners. You can find these along the route to Santa Monica. This is one route that screams old-school romance! It takes approximately 40 hours to complete this 2,500-mile route. The drive features plenty of history and interesting places to explore. Any road trip adventure from Chicago to Santa Monica is sure to be fun. Especially since you’ll be driving through the iconic Route 66 – a must-drive route for anyone who can drive.

However, it’s extra special for a couple to take on as the ‘Mother Road’ provides unforgettable memories at places like the Art Institute of Chicago, the Blue Dome Entertainment District, the Cadillac Ranch, the Petrified Forest National Park, and the Santa Monica Pier. Parking in Chicago is difficult but not impossible, but to be on the safe side, make sure to have a spot booked in advance before you head out!

2. Miami to the Florida Keys

romantic road trips

Not into retro diners and old-school romance? Well, the Miami to the Florida Keys romantic road trip route might be for you. So, what’s the fun in driving through a thin strand of pavement on top of long bridges surrounded by blue skies and a bluer ocean, you ask? Exploring one of the most underrated scenic routes with the love of your life. Period.

The entire romantic road trip would take around 3 – 4 hours to complete and stretches roughly 113 miles with 42 bridges. Make sure to include hotspots like Everglades National Park, John Pennekamp Coral Reef State Park, Rain Barrel Artisans Village, Lobster Statue, Curry Hammock State Park, and the Dolphin Research Center. There are also plenty of stops where you could go scuba diving and snorkeling across the route. All this makes this romantic road trip a must-do, especially for those couples who have a nose for adventure!

3. Los Angeles to San Louis Obispo

romantic road trip

Any road trip through the Pacific Coast Highway is worth taking. And when it’s a romantic road trip that starts from gorgeous Los Angeles, you can be sure it’s going to be spectacular! With so much to explore in LA, you should drive around the City of Angels before taking Highway 101 towards Ventura if you are not a resident. Iconic places of interest like the Hollywood Sign and the Hollywood Walk of Fame are great places to start your adventure as a couple.

There are so many parking spots in Los Angeles available online that you can spend lots of time in LA and never worry about parking. Once all the exploration of LA is done, you can start your romantic road trip from Los Angeles to San Louis Obispo. Recommended pitstops include the Funk Zone, the legendary Hotel California, the Hearst Castle, the Danish town of Solvang, and Ostrich Land. That said, if you have time to spare, you should also consider stopping at romantic destinations like the Santa Maria Valley.

4. San Louis Obispo to San Francisco

The 5 Most Romantic American Road Trips for Couples

With so many possibilities and so little time to completely explore the Pacific Coast Highway, you’ll be spoilt for choice. However, it would still be unfair to leave out the San Louis Obispo to San Francisco route from a list of romantic road trip routes through the United States. Starting from where we left off, start your romantic escapade with your loved one by exploring the wonders of San Luis Obispo.

Make sure not to miss attractions like Mission San Louis Obispo de Tolosa, Bubblegum Alley, Bishop Peak, and downtown SLO. Once that’s crossed off from the list, you can start your drive towards Highway 1 through Morro Bay towards the Pfeiffer Beach, all the way through Half Moon Bay, before reaching the Golden Gate Bridge entrance. Take in the views of the majestic bridge from the Marin Headlands. There are very few things in the world that are as romantic as watching the sunrise from this spot with your partner.

5. New York City to Shelter Island

New York to Shelter Island

We finish the list of best romantic road trip routes with one of the most underrated routes – NYC to Shelter Island. Yes, you read it right; we are talking about driving to an island with no bridges for a road trip. Casually situated between Long Island’s North and South Forks, Shelter Island is a majestic and dreamlike place to be. Had your fill of exploring New York City? Leave your parking spot in NYC and head straight towards either the North Ferry or South Ferry. These offer accessible ferry rides to Shelter Island.

You can drive out into the many untouched beaches and manor houses. They offer an entirely different experience from what you’ve previously experienced 0n the mainland. Looking for top places to visit on Shelter Island? You can include the Mashomack Preserve, the Shelter Island Historical Society, Wades Beach, and the Orient Beach State Park. A road trip from NYC to Shelter Island typically takes around 2 hours. It also spans over 100 miles in total, making it one of the best options for a Valentine’s Day trip.


Check out our blogs for info on finding top-rated airport parking, the best parking spots in your city, the most affordable insurance for your car, and top-rated car washes near you.

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