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5 Nostalgic Vacation Ideas to Remind You of Times Past



Have you ever come home from a vacation and felt like you needed another vacation? It seems like the more advanced our society becomes, the more hectic our lives become … even in our leisure time. Maybe what we all need is a chance to reconnect with simpler times, when we weren’t glued to our phones, distracted by emails, or bound by busy agendas. If you’re interested in taking a literal trip down memory lane, here are five vacation ideas that will transport you back to yesteryear.

Get Sprinkled With Stardust in Old Hollywood


During Hollywood’s Golden Age, iconic figures like Lucille Ball, Bob Hope, and members of the Rat Pack lived and played in Palm Springs, CA. To this day, the Old Hollywood charm lives on in this sunny desert town, and it’s a considered a mecca for its distinctive mid-century modern architecture. While its downtown is filled with modern restaurants, boutiques, and entertainment options, exploring it through the lens of classic Hollywood is one of the best ways to experience Palm Springs. Tour the homes and hideaways of celebrities like Frank Sinatra and Elvis, or better yet, book an overnight stay at the Bing Crosby Estate. Visit the Walk of Stars to discover the many famous figures who spent their time in Hollywood’s Playground. Once you’ve taken in all the glitz and glam, explore the area’s desert landscape and lush oases at the nearby Coachella Valley Preserve or Joshua Tree National Park.

Take It Easy at Martha’s Vineyard


Since the late 1800s, travelers have been retreating to this little island paradise just off the coast of Cape Cod, MA. The island stretches only 9 miles wide and 26 miles long and is accessible only by plane or ferry, providing a sweet escape from busy mainland life. No trip to Martha’s Vineyard is complete without a visit to Oak Bluffs, a neighborhood filled with over 300 colorful and elaborately designed gingerbread cottages originating from a 19th-century Methodist campsite. The Aquinnah Cliffs — multi-colored clay cliffs carved by glaciers millions of years ago — provide stunning views of the ocean and brilliant photo ops. With pristine beaches, numerous water sports, a vibrant arts and culture scene, and unique shopping and dining (no chain stores, hotels, or restaurants here), Martha’s Vineyard guarantees a one-of-a-kind experience for all. (Fun Fact: Nicknamed “Hollywood East,” the island has long been a popular destination for A-list celebs and past U.S. presidents.)

Meet Me at the (State) Fair


Livestock exhibitions, craft and baking competitions, carnival rides, live music, and deep-fried everything: these are all marks of the quintessential state fair experience — an old-school tradition dating back to America’s agricultural heydays. A trip to the state fair makes for a family- and budget-friendly outing where you can take part in many of the attractions that have been hallmarks of these events since the first state fair in 1841. Even better, you don’t have to venture too far from home to join in on the fun, although a trip to another state’s fair would be a fun adventure. Noteworthy festivals include the Minnesota State Fair, which is one of the largest in the nation and known for its bizarre foods, as well as the Great New York State Fair, the first and oldest state fair in the U.S. Visit tripsavvy.com for a calendar of 2018 fairs in every state.

Savor Southern Charm in Savannah, Georgia


With its cobblestone streets, Georgian-style architecture, and antebellum history, stepping into Savannah is truly like stepping back in time. This beautiful southern town will invite you to slow down while you soak up its rich heritage with activities like riverboat cruises, walking and trolley tours, and ghost tours. Visit the birthplace of Juliette Gordon Low, the founder of the Girl Scouts, and take in the stunning architecture of the Cathedral of St. John the Baptist, nicknamed the Sistine of the South. While a stroll through a cemetery may sound eerie, the Bonaventure Cemetery is filled with over 100 acres of history and beauty, providing breathtaking views of Savannah’s characteristic Spanish moss. In addition to its historic appeal, Savannah also has a thriving artistic and culinary scene, as well as lively nightlife. (Fun Fact: The park bench scenes from the 1994 movie “Forrest Gump” were filmed in Chippewa Square — now a popular spot for visitors to snap a photo.)

Get Your Kicks on Route 66


Nothing says vintage American vacation like the classic Route 66 road trip. Spanning from Chicago to Los Angeles, there are seemingly endless sights for you to see along the Mother Road. Go spelunking at Meramec Caverns, just an hour outside of St. Louis, MO. Drop by Shamrock, TX, for a tour of the famous art-deco style U-Drop Inn, a popular dining destination for highway travelers in its prime. Stop for a night at Wigwam Motel in Holbrook, AZ, where you can sleep in a traditional Native American wigwam outfitted with restrooms, TV, and air conditioning (#glamping). Wrap up your journey at the century-old Santa Monica Pier — the official stopping point of Route 66 — where there’s a variety of fun for the whole family to enjoy, including an amusement park, aquarium, and free historical walking tours.