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How I'd Spend a Perfect Day in My City for Under $50

Stefanie O'Connell

As much as I love a good Netflix marathon, I can only binge-watch for so long. And with summer coming to a close, I know I’ll be itching to get out and make the most of these warm sunny days.

The only catch? I live in New York City, where tickets to Hamilton are $350 (if you’re lucky) and chocolate chip cookies can cost $4 apiece. With price tags like these, even sensible staycationing can be a major budget buster.

Of course, consuming prohibitively expensive entertainment and artisan desserts aren’t the only ways to tour big cities, which can also be beacons of free and low-cost activities if you know where to look.

To prove it, we asked big-city dwellers to tell us how they’d spend a day off in their hometowns for less than $50. Here are five budget-friendly itineraries, starting with my own Big Apple guide.

Tour New York City’s Hot Spots by Bike

I’d kick off the morning in Brooklyn Bridge Park, taking in the Manhattan skyline and window-shopping in the surrounding DUMBO district. A quick peek at the park event calendar typically reveals a bonus freebie—a fitness class, kayaking, maybe even a music festival. (City park and library calendars are gold mines for finding freebies.)

Then I’d walk across the Brooklyn Bridge to City Hall and grab a $12 day pass for NYC’s bike-share program, Citibike. After a quick ride north to Astor Place, I’d spend some time exploring St. Marks Place and the many thrift shops and cultural treasures of the East Village. The 99-cent pizza joint offers the most budget-friendly lunch, but nearby Mamoun’s falafel is hard to beat with a hearty, healthy meal for less than $5.

From there, it’s a straight shot west to Washington Square Park, a perfect resting spot to people-watch. A few more minutes west, you’ll hit the Hudson River and the beautiful waterfront bike path, which I’d follow northbound to midtown. I’d make a right in the 40s and find a spot to dock my Citibike on 8th avenue, then try my luck at a Broadway show lottery. If I win, I’d enjoy my front-row theater seats for as little as $30. If I lose, I can head to the restaurants on 9th avenue in Hell’s Kitchen for happy hour to close the day out on a high.

Make Tacos and Beach-Lounging Your Mission in Los Angeles

Jackie Lam, 34, founder of Cheapsters.org

“I love mission-based staycations—to hit all the best ice cream parlors, curio shops or hotel pools you’ve been dying to visit in your city. In this case, I’d go on the hunt for the best tacos. In L.A., tacos are relatively cheap at places like Kogi Taqueria in West LA and Cerveteca in Venice beach, so you can try a variety. Each meal, including a drink, would cost roughly $8 to $12.

After lunch at Kogi, I’d hop on my bike and ride down to Santa Monica and Venice (for my second round of tacos later that afternoon) to enjoy the afternoon at the beach for a while. From Santa Monica, I’d ride down the beach bike path another 15-20 minutes, over to the Annenberg Community Beach House, where you can check out the work of resident artists at the Marion Davies Guest House. You don’t need to make reservations to visit the house itself, but you do need to reserve a spot if you want to take a dip in the pool or lounge poolside. (Cost: $10 for each adult.)

I’d then head over to the Santa Monica Pier. If the pier isn’t too packed, I’d also go for a quick ride on the ferris wheel, which offers a beautiful view of the ocean and is just $5 for a single ride.

I’d probably be worn that from all that biking, swimming and taco-eating, so I’d take the Metrolink back home ($1.75 for a single fare).”

Go Museum- and Landmark-Hopping in Chicago

David Winchell, 39, financial planner and founder of Winchell’s Wealth Management

“I would center my day around checking out the (free!) Lincoln Park Zoo and a trip to one of the amazing museums in Chicago. They’re all very reasonably priced, and many even offer special free days.

I have three young children, so after the zoo, we’d take the bus ($2 each) to Millennium Park to enjoy a picnic lunch before walking over to Chicago’s famed Navy Pier to stroll through the gardens and along the waterfront while taking in the downtown horizon. On summer Wednesdays and Saturdays, there’s also a free fireworks show.

I’d then walk over to Michigan Avenue’s ‘Magnificent Mile’ for prime window-shopping and a visit to the free Richard H. Driehaus Museum, where we’d check out the art and architecture of America’s Gilded Age right in downtown Chicago.

Finally, we’d stop into Chicago-based burger joint M Burger for some delicious, cheap eats (you can get a burger for as little as $4.50) and a milkshake ($3.50) to round out the day.”

Hit the Beach and Art District in Miami

Amanda Abella, 28, author of “Make Money Your Honey

“If the weather is nice, I’d start my day off at the beach with a home-packed picnic, a good book and maybe a journal, in case I feel like doing some writing.

I’d take the bus to Miami Beach—no pass needed—for about $4.50 to save money on gas and parking. From there, I’d get off on Washington Ave and Lincoln Road and walk the few blocks to the beach. (This area of the beach is a bit less touristy than Ocean Drive.)

I could spend all day by the water, but if I feel like checking out some architecture, I’d walk down another couple blocks to Lummus Park. The path in the park allows you to peek into the beautiful pool and bar areas of some of the hotels and condos.

I’d then take an Uber to Wynwood, Miami’s vibrant art district, which would cost about $10 depending on the day—though you can check out Uber Pool for deals as low as $3.50. I’d start off at Wynwood Walls, a free, public park with walls full of art, then wander around and check out the various galleries. Festivals like Art Basel (December 7-10) and monthly “art walks” are your best opportunities for maximizing freebies.

As for dinner, Wynwood is full of local, award-winning restaurants without the Miami Beach price tag. (Zak the Baker and The Salty Donut are all the rage right now for baked goods.)

Lastly, I’d probably drop in and see what’s going on at one of my favorite new-age shops in the area. They sometimes have workshops or low-cost events (I’m talking $5). I once ended up viewing an exhibit of Tibetan monks working on a sand mandala!”

Enjoy Nature and People-Watching in Denver

John Schneider, 42, co-founder of DebtFreeGuys.com

“I’d start my day with yoga at Red Rocks Amphitheater. Doing yoga while watching the sunrise over downtown Denver is inspiring and relaxing—and costs nothing. There’s always the option to join in on Yoga on the Rocks for $12, but since there’s no fee to enter Red Rocks when there isn’t a show, you can do your own yoga for free anytime.

Afterwards, I’d take advantage of Olive & Finch’s curbside service and order their Green Eggs and Sam breakfast sandwich with focaccia and basil pesto for just under $12, including tax and tip. I’d then clean up at home, grab my bike and ride one of Denver many downtown bike paths. My favorite starts on Colfax Avenue, a major road through downtown Denver, and ends in LoDo (Lower Downtown).

I’d then stop at Denver’s Museum of Nature & Science, which has an entrance fee of $15. Along with its amazing IMAX experience, the museum hosts one or more impressive exhibitions at a time.

Then I’d hit the road and finish the roughly four-mile ride at Denver’s new and refurbished Union Station. Union Station is a 100-year-old landmark that was once the major transportation hub of the city. It’s since become home of an eclectic mix of restaurants, bars, shops and hotels and connects the heart of downtown to the Denver International Airport.

To quench my thirst, I’d order a glass of Colorado’s own Avery Brewing Company’s ‘Joe’s Pils’ for $5 at The Terminal Bar. While I’d drink my beer, I’d sit in the center of the station and enjoy some of the best people-watching in Denver and play free shuffleboard.

Then I’d get back on the road to return home. On my way, I’d stop at Tag Burger Bar and get the Lady Gaga turkey burger for $12, which includes whipped mozzarella, basil pesto, grilled red onions, a balsamic vinegar glaze and fries. In total, my staycation would cost me a couple bucks shy of $50.”

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