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Follow the compass and Cupid’s arrow to the long weekend of your dreams

By Katie Morell

Few experiences are more romantic than hopping in your car and heading out for a weekend away. Regardless of your location, there are several road trip options that are perfect for you and your sweetie. Read on for a few three-day itineraries to get you started—a smooth ride in a stylish Malibu may be just the adventure Cupid has in mind.

Road Trip #1: Santa Barbara—Los Angeles—San Diego

California’s Highway 1 is arguably the most scenic stretch of pavement in the world. Take advantage of the February sun and get started in picturesque Santa Barbara with a visit to the city’s Botanic Garden. From there, stop for lunch at Chuck’s Waterfront Grill and enjoy the sea views.

Check in to West Beach Inn, a 46-room property right on the water, and head out to visit a few wineries on the Santa Barbara Urban Wine Trail (Cottonwood Canyon, Whitcraft Winery, Carr Winery). Eat dinner at Opal Restaurant and Bar; then take in a show at the Granada Theatre.

The next day, drive south to the idyllic community of Malibu. Follow the park signs to some great hiking, and grab a bite to eat at Neptune Net, a fried-food joint that’s a local favorite.

Continue south to Santa Monica and check in to Shutters on the Beach. Rent bikes and take the beachside path to Venice Beach and Manhattan Beach. After cycling back to Shutters, walk over to The Lobster, a restaurant on the Pier, for some of the best seafood you’ll ever eat.

In the morning, steer your Malibu south for the two-hour drive to San Diego. Check in at Tower23, a boutique hotel with modern touches that sits directly on Pacific Beach. Once settled, drive up to La Jolla, take a paddle-boarding lesson and then bop over to Balboa Park for a stroll through the property’s gardens and museum. Once you’ve built up an appetite, settle in at Café Chloe, an adorable bistro in San Diego’s East Village neighborhood that regularly features live jazz performances.

Road Trip #2: Chicago—Grand Haven—Traverse City

Yes, it may be a bit brisk outside, but Chicago is still a perfect spot to start a Valentine’s Day road trip. After a handholding spin with your love at McCormick Tribune Ice Rink, walk a few feet to Cloud Gate, a.k.a. the ‘Bean,’ a reflective art sculpture.

Continue walking north (1.6 miles) along Michigan Avenue to the John Hancock Building, and check out the myriad shops and restaurants. Head up to the 95th floor to The Signature Room, a cocktail lounge with a view of the entire city. Sip a glass of wine before walking a few blocks to The James, a boutique hotel. Finish off the night at Tru, a high-end restaurant where Chef Anthony Martin will treat you to an unbeatable six-course tasting menu.

On your second day, drive north along Lake Michigan to Grand Haven, Michigan. Check into Boyden House, a historic bed and breakfast. After dropping off your luggage, walk a few blocks west into downtown and grab some tasty fish and chips at Pavilion Wharf Bar & Grill.

Round out your three-day road trip by driving north to Park Place Hotel in Traverse City, known for its outdoor winter sports. Spend the day downhill skiing at Shanty Creek Resort’s Schuss Mountain. Dine at The Cook’s House, a restaurant that creates dishes from local and sustainable food sources.

Road Trip #3: Nashville—Memphis—Tunica

Are you a couple of music fans? If so, start off in Nashville. Begin your day with a visit to the Country Music Hall of Fame. From there, grab lunch at Marché Artisan Foods, a café in the East neighborhood.

Check in to the Hermitage Hotel, a five-star property that’s been around for more than a century, and get ready for a night on the town. Have a drink at the Bluebird Café, a hot performance spot for up-and-comers, and dinner at F. Scott’s, an elegant restaurant with more than 300 wines and live music almost every night.

The next morning, drive three hours west to Memphis. Check in to the beautiful Peabody Hotel, then grab lunch at Central BBQ, a restaurant known for its authentic southern cooking. From there, stroll through the South Main Arts District or visit the National Civil Rights Museum.

On the morning of your third day, drive to the city of Tunica, Mississippi, and check in to The Columns of Tunica, a southern-style bed and breakfast. Get a bite to eat at Hollywood Café (make sure to try the fried dill pickle), then burn off the lunch calories with a round of golf at Tunica National. End your day at Twain’s, a fine restaurant at Sam’s Town Casino.

Road Trip #4: Stowe, Vt.—Providence, R.I.—Cape Cod, Mass.

After checking in to Stowe Mountain Lodge, put on your snowshoes and head out on a hike with The Green Mountain Club. For lunch, ask for a table overlooking mountain scenery at Crop Bistro & Brewery. Stowe is also known for its spas, so make time for a couple’s massage in the afternoon at Spa at Stoweflake. End the day with a horse-drawn sleigh ride at Trapp Family Lodge and dinner at the famous Michael’s on the Hill.

Early the next day, drive four hours south to Providence, Rhode Island. Check in to the adorable, boutique Hotel Providence and strap on some ice skates for a twirl around the rink at the Bank of America Skating Center—twice the size of New York City’s Rockefeller Plaza. From there, grab lunch at Local 121 in downtown Providence. Shop boutiques along Washington Street or spend the afternoon gazing at Monets and Picassos at the Rhode Island School of Design’s Museum of Art. End the day with dinner at Gracie’s, a local haunt in Providence’s Federal Hill neighborhood.

Finally, drive east to Cape Cod and check in to Land’s End Inn in Provincetown, Massachusetts, built in the early 1800s. Stroll the seashore, duck into small shops and try the freshly caught halibut at Mews Restaurant & Café for dinner.

The trademarks mentioned in this story are held by their respective owners.

Katie Morell is a San Francisco-based writer and editor.


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