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Fatherly Advice: 7 Cities That Are Just Perfect for a Trip with Dad

father and son taking a selfie
Written by Dhinesh Manuel

If you want to spend some time with Dad, don’t just settle for doing a cliché brunch or dinner. Instead, why not look for some cheap flights for Father’s Day weekend, block your calendar, and venture out into new, undiscovered frontiers, and take the old man with ya? Here are 7 places that are just perfect for a trip with Dad!

Las Vegas

People playing poker in the casino, roulette, gambling

Maybe Dad was always a bit of a gambler. Maybe he still likes to take a risk or two. Well, there’s no better place to test your luck than the roulette tables in Vegas. But there’s more to Sin City than just the casinos. Take Dad to his first Cirque du Soleil show. Treat him at some of the amazing restaurants and all-you-can-eat buffets in town. If it all just gets a little tiring, just chill back at the hotel pool over a few cocktails.

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Mexico City, Mexico

Maybe a first trip south of the border could be great for some father-child bonding, and what better place to visit than amazing Mexico City? Dive head first together into its bustling street markets. Learn more about Mexico’s rich Mayan heritage at the National Museum of Anthropology. Let Dad try his first grasshopper tacos from a street cart. Down copious amounts of tequila and make friends with the locals at highly entertaining lucha libre wrestling bouts.


Chicago skyline and river, Illinois, USA

If baseball is Dad’s sport of choice, he would never say no to catching a game at Wrigley Field! Even if he’s not into America’s favorite past time, Chicago can offer plenty of other great experiences like sharing a deep-dish pizza at Lou Malnati’s, standing in the glass box on the 103rd floor of the Willis Tower, or taking a very informative and enjoyable river cruise by the Chicago Architecture Foundation (trust us, he’ll love the interesting stories behind some of the greatest buildings in the world).

Montreal, Canada

If Dad’s always fondly talked about his short time in Paris when he was younger, then why not relive the memories at a closer…and very similar…location? Montreal is just a short flight away from the East Coast, and has plenty of fantastic architecture, food, and history. Stroll down the charming cobblestone streets of Vieux Port (Montreal’s oldest neighborhood). Dig into some hearty poutine. Have a few beers in the trendy Mile End neighborhood. There’s so much that he will enjoy in this one-of-a-kind city.

New Orleans

French Quarter, New Orleans

Is Dad fond of jazz and great seafood? The Big Easy has plenty of great live music, bars, and shows, and some great neighborhoods with lots and lots of history. Take Dad to his first visit to a Voodoo shop and even get him a tarot reading. Take a tour of some of the city’s iconic and beautiful cemeteries, and see the final resting places of some of its most famous denizens. You can even stop by the famously haunted Lafitte’s Blacksmith Shop Bar to gulp down a few heady spirits.

You may also like: Weekend Trips to Take with Your Dad: Where to Go & What to Do

Havana, Cuba

How about you give Dad the chance to step into a time machine to a by-gone era? Welcome to Havana! Colorful classic automobiles whizz through the streets and the old Spanish colonial buildings have so many stories to tell. Visit the Hemingway House, the legendary author’s home in Havana, and drop in for a daiquiri at one of his favorite watering holes, Floridita. Give Dad his first salsa lesson and catch up on old times over a bottle of fine Cuban rum.

New York City

Beautiful foliage colors of New York Central Park.

Introduce Dad to the magic of the Big Apple. Even if he’s been many times before there’s always something new to rediscover in “the city that never sleeps.” Catch a Broadway show. Eat out at one of the city’s many amazing multi-cultural eateries. Walk through Central Park and sit down on a bench over a cup of joe while people watching. Sing along at many of its raucous piano bars. Snap a few selfies in Times Square and make a trip out to the Statue of Liberty and Ellis Island.

Know any other cities that are just perfect to catch cheap flights for Father’s Day? Let us know in the comments below!

About the author

Dhinesh Manuel

Socialite, philanthropist, costumed crime fighter by wait...that's bad ...

Musician, writer, travel junkie, dog lover, and database of useless information. I love to learn about new cultures, experience new cuisines, meet new people, and have a few laughs along the way!

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