Chicago, Santa Monica and New York: 5 romantic road trips for couples for Valentine's Day

By TravelWiseFeb 14, 2024 19:34 PMNews
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Chicago, Santa Monica and New York: 5 romantic road trips for couples for Valentine's Day
Spice up your Valentine's Day with a romantic trip. Source: Freepik

February is here and love is in the air! If you're tired of monotonous Valentine's Day celebrations, why not spice things up with a romantic trip? Forget about banal candlelit dinners and carriage rides and hit the road with your soulmate.

Imagine planning and exploring the most romantic places in America, hand in hand with your partner. It's time to add a little adventure to your love life, and a road trip is the perfect way to do it!" writes kansas.com.

Way.com offers you a variety of routes and even a playlist for a romantic road trip. If you're seriously considering planning a romantic road trip for Valentine's Day, you should check out these five romantic road trip routes. Pro tip: Don't worry about parking problems and find guaranteed parking spots. Get out your maps and let's dive into these romantic road trips right now!

Chicago -Santa Monica

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

This epic 2,500-mile adventure is a throwback to old-school romance. There are many surprises and hidden gems along the way. From historical landmarks to quirky attractions, this 40-hour trip promises to be an unforgettable experience that will leave you breathless and wanting more!

Any adventure on the road from Chicago to Santa Monica is bound to be interesting. Especially since you will be traveling along the iconic Route 66. However, for a couple, this trip will be especially interesting, because the "Mother Road" gives unforgettable memories in places such as the Art Institute of Chicago, the Blue Dome entertainment district, Cadillac Ranch, Petrified Forest National Park and the Santa Monica Pier.

Parking in Chicago is difficult, but not impossible. To be on the safe side, make sure you reserve a spot in advance before you hit the road!

Chicago, Santa Monica and New York: 5 romantic road trips for couples for Valentine's Day
Petrified Forest National Park. Source: @Finetooth, wikipedia.org

From Miami to the Florida Keys

Don't like retro diners and old-school romance? Then the Miami - Florida Keys romantic route might be for you. You may ask, what's so interesting about driving along a thin strip of sidewalk over long bridges surrounded by blue skies and blue ocean? Exploring one of the most underrated scenic routes with your loved one. Period.

The entire romantic journey will take about 3-4 hours and stretch for about 113 miles with 42 bridges. Be sure to visit places of interest such as Everglades National Park, John Pennekamp Coral Reef, Rain Barrel Artisans Village, Lobster Statue, Curry Hammock State Park, and Dolphin Research Center.

There are also many stops along the route where you can go diving and snorkeling. All this makes this romantic trip a must, especially for those couples who love adventure

From Los Angelesto to San Luis Obispo

Any trip along the Pacific coast is worth taking. And when it's a romantic trip that starts in gorgeous Los Angeles, you can be sure it's going to be spectacular!

There's so much to see and do in Los Angeles that it's worth a drive through the City of Angels before heading down Highway 101 towards Ventura if you're not a local. Iconic landmarks like the Hollywood sign and the Hollywood Walk of Fame are great places to start your trip as a couple.

In Los Angeles, there are so many parking spaces available online that you can spend a lot of time in Los Angeles and never worry about parking. After you explore Los Angeles, you can start a romantic road trip from Los Angeles to San Luis Obispo.

Some of the recommended stops include the Funk Zone, the legendary Hotel California, Hearst Castle, the Danish town of Solvang, and Ostrich Land. However, if you have some free time, you should also consider staying in romantic places like the Santa Maria Valley.

From San Luis Obispo to San Francisco

Chicago, Santa Monica and New York: 5 romantic road trips for couples for Valentine's Day
Embark on a Valentine's Day trip from San Luis Obispo to San Francisco. Source: Freepik

With so many options and so little time to fully explore the Pacific Coast, you'll be spoiled for choice. However, it would be unfair not to mention the San Luis Obispo - San Francisco route on the list of romantic road trips.

Let's pick up where we left off and plan a romantic road trip 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.

Don't miss out on attractions like the Mission San Luis Obispo de Tolosa, Bubblegum Alley, Bishop's Peak, and downtown SLO. Start by crossing items off your list before driving on Highway 1 through Morro Bay to Pfeiffer Beach. Continue through Half Moon Bay to San Francisco, where you can drive through the city to the entrance of the Golden Gate Bridge.

Enjoy the view 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.

New York - Shelter Island

We finish the list of the best romantic road trips with one of the most underrated routes - from New York to Shelter Island. Yes, you read that right, we are talking about a trip to an island without bridges for a road trip.

Chicago, Santa Monica and New York: 5 romantic road trips for couples for Valentine's Day
Embark on a road trip from New York to Shelter Island. Source: Freepik

Located between the North and South Forks of Long Island, Shelter Island is a majestic and fabulous place to visit. Are you tired of exploring the Big Apple?

Leave your parking spot in New York City and head straight to the North or South Ferry. From them, you can get to Shelter Island at affordable prices. You can drive out to the numerous pristine beaches and estates. They offer a completely different experience than the one you used to have on the mainland.

Looking for the best places to visit on Shelter Island? These include the Mashomack Preserve, the Shelter Island Historical Society, Wades Beach, and Orient Beach State Park. It usually takes about 2 hours to get from New York to Shelter Island. The island is over 100 miles long, making it one of the best options for a day trip on Valentine's Day.

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