view from the trunk of a car of a sunset, legs of two people laying side-by-side visible
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5 romantic road trips for couples this Valentine's Day

Written by:
February 2, 2024
Andrey Yurlov // Shutterstock
This story was produced by Way and reviewed and distributed by Stacker Media.

5 romantic road trips for couples this Valentine's Day

February has arrived, and love is in the air! If you're tired of the same old Valentine's Day celebrations, why not spice things up with a romantic road trip? Forget the cliched candlelit dinners and carriage rides, and hit the open road with your special someone. After all, they say that couples who travel together, stay together. (Okay, we may have made that up, but it's true!) Imagine planning and exploring the most romantic destinations across America, hand in hand with your partner. It's time to add some adventure to your love life, and a road trip is the perfect way to do it! has 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 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!

Santa Monica pier
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Andreas Aydt // Canva

1. Chicago to Santa Monica

Imagine starting your journey by sinking your teeth into a slice of mouth-watering deep-dish pizza and hitting the road to explore the many fascinating roadside diners that dot the route to Santa Monica!

This epic 2,500-mile adventure is a throwback to old-school romance. There are plenty of surprises and hidden gems waiting to be discovered along the way. From historic landmarks to quirky attractions, this 40-hour drive promises to be an unforgettable experience that will leave you breathless and craving for more!

Any road trip adventure from Chicago to Santa Monica is sure to be fun. Especially since you'll be driving along the iconic Route 66. 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!

Bridge to Florida keys
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Gagliardi Photography // Canva

2. Miami to the Florida Keys

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!

two people walking in montana del oro state park near San Luis Obispo
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joojoob27 // Shutterstock

3. Los Angeles to San Luis Obispo

Any road trip along 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 Luis 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.

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Joshua Resnick // Shutterstock

4. San Luis Obispo to San Francisco

With so many possibilities and so little time to completely explore the Pacific Coast Highway, you'll be spoiled for choices. However, it would still be unfair to leave out the San Luis Obispo to San Francisco route from a list of romantic road trips. Let's continue from where we left off and plan a romantic getaway to San Luis Obispo. This charming town has a lot to offer, so you and your partner can start your adventure by exploring its many wonders.

Make sure not to miss attractions like Mission San Luis Obispo de Tolosa, Bubblegum Alley, Bishop Peak, and downtown SLO. Start by checking off your list before driving towards Highway 1 via Morro Bay towards Pfeiffer Beach. Keep driving through Half Moon Bay to San Francisco, where you can drive through the city  to the Golden Gate Bridge entrance. Take in the views of the majestic bridge from the Marin Headlands. Watching the sunset from this spot with your partner is one of the most romantic experiences in the world.


Sunrise on the Mashomic Preserve on Shelter Island, NY
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Paul G Gallery // Shutterstock

5. New York City to Shelter Island

We finish the list of best romantic road trip routes with one of the most underrated routes – New York City 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 the Big Apple? 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 on 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 day trip.

This story was produced by and reviewed and distributed by Stacker Media.

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