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This Father’s Day, Take Dad to One of These Amazing Cities!

Father son vacation
Written by Dhinesh Manuel

This blog post was updated on June 13, 2022.

If you want to spend some time with Dad, don’t just settle for doing a cliché brunch or dinner. Instead, why not block your calendar, and venture out into new, undiscovered frontiers with your old man? After all, there’s no better present than the gift of travel. Here are seven cities that are just perfect for a trip with Dad!

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 isn’t too far from the East Coast, so book a couple of quick business class flights to Canada and enjoy its 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 for your dad to enjoy in this one-of-a-kind city.

Las Vegas, Nevada

Las Vegas

Believe it or not, there’s more to Sin City than just the casinos. Take Dad to his first Cirque du Soleil show. Treat him to some of the amazing restaurants and all-you-can-eat buffets in town. If your dad’s an adrenaline junkie, there maybe spring for a helicopter tour over the Grand Canyon. If you and Pops get tired, just chill at the hotel pool with a few cocktails. 

Mexico City, Mexico

Maybe taking your first trip south of the border would 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 taco from a street cart. Down responsible amounts of tequila and make friends with the locals at highly entertaining lucha libre wrestling bouts.

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

Chicago, Illinois

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 pastime, Chicago can offer plenty of other great experiences. Share a deep-dish pizza at Lou Malnati’s, stand in one of the terrifying glass boxes on the 103rd floor of the Willis Tower, or take a very informative and relaxing river cruise by the Chicago Architecture Foundation. Trust us, Dad will love the interesting stories behind some of the greatest buildings in the world.

For an added dose of culture, check out the Art Institute of Chicago, one of the finest art museums in the world, and home to Edward Hopper’s Nighthawks, Grant Wood’s American Gothic, and Georges Seurat’s A Sunday Afternoon on the Island of La Grande Jatte. Chicago is almost an embarrassment of riches!

New Orleans, Louisiana

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 on his first visit to a Voodoo shop and get him a tarot reading. Take a tour of some of the city’s spectacular cemeteries. Yes, cemeteries! Trust us, you haven’t lived until you’ve seen how some New Orleans residents have chosen to spend eternity. You can even stop by the famously haunted Lafitte’s Blacksmith Shop Bar to gulp down a few heady spirits.

Havana, Cuba


How about you give Dad the chance to step into a time machine to a by-gone era? Welcome to Havana! Yes, Americans are now allowed to travel to Cuba, although the U.S. government has some restrictions on why you can travel there and where you can spend your money, so definitely do your research. But once you get there, you’ll be glad that you did. 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 discover 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 one of the many 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 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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