Last updated on June 30, 2024. Original publish date: July 30, 2018

Best Cities for Fun Summer Getaways

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There’s something magical about summer; it’s more than backyard barbeques and pool parties. In order to really appreciate your vacation time, sometimes you have to get out of the house and go on a road trip to make memories that will last a lifetime. And to inspire your adventurous getaway spirit, Metropolitan Shuttle has put together a list of awesome tips from road tripping travel insiders to help plan your summer adventure.

For those wanting some Southern flavor, head to Charleston, South Carolina, a favorite travel destination of Kika, a travel influencer. While New York, Boston, and Los Angeles are popular cities will well-grooved tourist tracks, Kika prefers the old-fashioned charm of Charleston, South Carolina. According to Kika, “Everyone I encountered was friendly and made me feel welcome. The food is also very memorable. I went to the award-winning Hyman’s Seafood and the service was impeccable. I definitely recommend their hush puppies! Southern Coney and Breakfast is a great diner to go to if you are looking to meet locals. Charleston is a city that makes you feel comfortable when you’re walking around and the vistas are straight out of a storybook. For those seeking nightlife, I recommend The Boardroom. It has good drinks and the live band was very engaging and talented.”

When it comes to getting around Charleston, take the worry and hassle out of your holiday by chartering a bus. If you don’t feel like driving, it’s a surprisingly economical and relaxing way for groups to travel with confidence and ease. Another transportation option is a free trolley that operates throughout the historic Charleston Peninsula. Part of the CARTA bus system, it offers routes to sight-seeing highlights, including the Aquarium and the Riley Waterfront Park, an idyllic oasis that offers spectacular views of the harbor. With park benches, picnic tables, and a large lawn, the park makes the perfect spot for a lazy afternoon by the water. On the way there, stop by The Market nearby and peruse the exclusive specialty foods from Gita’s Gourmet, your picnic basket headquarters.  

Following the rays of sunshine along the East Coast, Cori Sue of Bitches who Brunch, suggests Savannah, Georgia, for a less traveled destination. It oozes Southern charm with incredible architecture and amazing cuisine, including Gerald’s Pig and Shrimp, a food truck that serves Deep South comfort food like Georgia shrimp po-boys and hand-squeezed limeade.  

Further north, she recommends Portland, Maine, for a different flavor of New England character as well as plenty of outdoor fun. Upstate New York has lots of mountains, rivers, and cute towns, villages, and wineries to explore. Woodstock, Vermont also is recommended for its “gorgeous views and killer, highly instragramable drive-in restaurants.” For a casual, on-the-go meal before your next adventure, stop in at The White Cottage Snack Bar, which has been proudly serving up classic diner food like burgers, sandwiches, and seafood since 1957.

Vanessa Valiente, a travel influencer, always makes time in her schedule for a pit stop in San Diego, Chicago, and New Orleans. For San Diego, Vanessa raves about the largest Little Italy in America – “You must go to the farmer’s market on Saturdays, and there are different neighborhoods for all preferences. With an average temperature of 72° and constant activity day or night, anyone can have an amazing visit here!” A must-see is Balboa, a sprawling 1,200-acre urban park in the heart of the city. Whether you meander through the gardens or stop in at the San Diego Zoo, the combination of culture and nature makes it a pleasant summertime destination.

Vanessa also recommends visiting Chicago. “Chicago feels as if Manhattan and San Diego had a baby. You get the hip hustle and bustle of Manhattan with the water lifestyle of San Diego. Folks are kayaking mere feet away from a skyscraper filled with $20 cocktails being sipped by people you want to know.

And everyone is insanely nice –All to a background of magnificent architecture, textured history, and teal waterways. I also love it for being a day city and night city. High energy people can find action at all waking hours in spring and summer.” For art lovers and intellectuals, a visit to the Museum of Contemporary Art (MCA) is the perfect place to cool off on the hottest summer afternoons. While staying cool and refreshed in the air conditioning, enjoy a dose of cultural enrichment when you peruse a rotating collection of modern and post-modern art.

She also can’t say enough about New Orleans, another popular destination for visitors. “New Orleans is amazing for drinking, air boating, dancing and eating – All set to a rich ambiance of historic balconies, lazing fauna, and soulful music. This city is so alive with a good time you can feel it on your skin, and like all my favorite cities, there is something to do, day or night.” First order of business is a pit stop at the French Quarter Market for a stylish hat, the must-have accessory for keeping you protected from the sun. After shopping for your party wardrobe, reward yourself with traditional New Orleans specialties like muffaletta and po-boy sandwiches.

Whether you’re planning on boozing it up on Bourbon Street in New Orleans or opting for a more elegant winery visit in upstate New York, consider hiring a charter bus for peace of mind for your summer adventure. You can have fun and bring the whole gang!

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