What to Do in Orlando if You're 50+

Here’s what to do in Orlando if you’re 50+.

Orlando Museum of Art. It’s not mentioned elsewhere in this post, but I highly recommend it.

Orlando Museum of Art. It’s not mentioned elsewhere in this post, but I highly recommend it.

I’ll be traveling soon, and two active “of age” couples are stepping in to vacation in the Florida sunshine at my West Orange home while watching my pesky pups. I had this request from one: “What to do when you're an over-60 intellectual and getting married again and neither of you has ever had a ‘real’ honeymoon.” Adding detail, she wrote, “We love theater of all kinds, we love live music (classical, jazz, opera). We are bookish. [My husband] isn't a good walker due to arthritis, so things that require a lot of standing and walking are a problem. We are light eaters. None of that says ‘Orlando.’"

They asked the right gal. Here’s what I told them, pasted in with minor changes for brevity (and minus the “Ask for so-and-so and tell him you’re my friend” asides), so forgive the sloppy writing. If you’re in Orlando and not in the mood for theme parks, take a look at these ideas. Then get outside and go have fun.


Dr. Phillips Center for the Performing Arts The best theater in town, and the most expensive. Buy tickets in advance. You’ll need to pay for parking nearby or at the valet. But, this is a stunning new theater complex with two existing theaters and two more on the way — one will be encased in air or rubber or something for perfect sound. The smaller theater has some nice jazz performances. Downtown Orlando.

Mad Cow Theatre Two small theaters, usually with very good plays. Cheaper but not super-cheap. Again, you’ll need to pay for parking nearby. One garage is in the same building. Groupon often has good deals on tickets.

Orlando Shakes Another good small theater. Does not only have Shakespeare plays despite the name. Ample free parking.

Garden Theatre Not as good theater-wise, but this is a small theater right near the house in historic downtown Winter Garden. The interior is old, with the coolest oddest Juliet balconies on the sides. Less expensive than the others. Ample free parking in the three-story garage behind the building.

The funky, historic Garden Theatre

The funky, historic Garden Theatre

The Orlando Philharmonic Orchestra The Philharmonic is quite good but it is homeless until the Dr. Phillips Center expansion is complete, so venues vary.

Orlando Opera This is homeless until the venue is complete too, so again venues vary for now.

Only in Orlando

Timucua Intimate three-story theater in a local couple’s home. It hosts concerts regularly, often with an artist creating something on stage as the musicians play. It’s usually free. Folks just show up, bring a snack or bottle of wine to share at a communal table (or donate $10), and take their seats. I know Timucua sounds weird, but I promise you it’s a wonderful little-known experience with a quirky, cultured crowd.

Timucua, also known as the White House

Timucua, also known as the White House

FAVO Arts Village The first Friday of every month, FAVO Arts Village opens as a free collection of art galleries. It’s a decrepit old motel that is filled with art galleries in every former guest room. It’s lively and colorful and filled with interesting people – and free.

The Attic Door This laid-back lounge in Winter Garden has live low-key music I believe Thursday-Sunday, but check. It’s free, but you’ll want to get a drink, including hot cider or hot chocolate, or maybe a nibble. There’s a fun trivia night on Tuesday evenings; arrive early to get a decent seat. The new owners are adding afternoon tea. Motto: "If you can't eat it on a sofa, it isn't on the menu!" (Note: As of January 3, 2019, The Attic Door was closed for a week or two so the new owners can set up. Call before you go.)

Enzian Theater Wonderful theater with independent and foreign films, plus it serves moderately prices meals at your table. It’s an inexpensive night out with a nifty group of people.



West Orange Cinema – Inexpensive movie theater. You can buy some crappy food plus wine and beer. 1575 Maguire Rd., Ocoee. There is a fancier, more expensive theater with good leg-rest chairs and delivered food at a place called Hamlin. I haven’t been yet, but it’s farther and nicer.

Kayaking Wekiwa If you’re outdoorsy this is a great place to rent a canoe or kayak. You can also just hang out in the park, grab one of the grills and have a picnic.

Wine Bar George Even if you’re not drinkers, this is a nice place to relax. It’s a wine bar and restaurant with plates meant to share in Disney Springs. Nice crowd. Free parking, but it’s a bit of walk from the lot.

Giraffe Ranch or its sister property, Safari Wilderness. Both are a bit far, but they’re excellent. They’re essentially African safaris on Florida land. You have to reserve by phone in advance. Sometimes you can get a Groupon.

Tiffany Museum Officially called Charles Hosmer Morse Museum of American Art. Amazing collection of stuff made by the Tiffany guy, including his Long Island patio, rebuilt here, and sometimes a chapel he built for the World’s Fair.

Boat tours Boating for the non-boaty! There are three leisurely boat tours that bring you amid chains of lakes. They show you wading birds, the backs of mansions … they’re kind of surprisingly nice for an hour or two. List from closest to the house to farthest: (If you do the Mount Dora one, make a day of it. It’s far, but a cute little town to tour.) Orlando Lake Tours, Scenic Boat Tour (and near the museum above, so you can make a day of it), and Dora Canal Tours.

Airboats Florida Cracker fun. They’re all different, so google and see what looks good.

Rollins College Speaker Series Sometimes has great stuff.

SNAP!’s City Unseen Exhibit Augmented reality exhibit that will bring you to cool parts of Orlando. Download the app, then drive to the designated parts of town. Start at Mills 50, which is nifty on its own because utility boxes, building exteriors and even dumpsters are painted creatively by local artists. When you get to the exhibits, you use the app to scan a code, then you see art through your phone instead of what’s really there.

SNAP!’s City Unseen augmented reality exhibit

SNAP!’s City Unseen augmented reality exhibit

Leu Gardens – Botanical gardens with free movies on weekend nights, I believe, plus a historic home to tour.


Things to Do in Orlando that Aren’t Theme Parks

5 Unexpected Orlando Cultural Finds

4 Friendly Towns That Make for Great Orlando Day Trips

What to Do in Orlando

Also check out the Insight Guides guidebooks to Orlando and Florida I updated lately, and go to the Orlando Weekly website for a thorough listing of events.

Orlando Date Night Guide lists tons of things to do at all price levels.

Cool West Orange Places for Food and Beverage

These recs are for folks staying in or near the West Orange area of Orlando – Windermere, Winter Garden, Ocoee and maybe Dr. Phillips.

Plant Street Market – Food hall and brewery, plus a juice bar with raw and vegan foods, a pizzeria, a mac ‘n’ cheese specialist, a coffee guy, a raclette (melted cheese) guy, a tea guy and more. Nice place to sit outside and watch the world go by, and that’s free. 426 W. Plant St., Winter Garden.

Plant Street Market, a food hall with the Crooked Can Brewery inside

Plant Street Market, a food hall with the Crooked Can Brewery inside

Winter Garden Farmers Market – Saturday mornings. Biggest farmers market in Florida. Live music with chairs to listen. Relaxing to stroll around. Many of the same vendors as the Sunday Lake Eola Market. Park for free in the brick 3-story lot. 104 S. Lakeview Ave., Winter Garden.

Downtown Winter Garden in general – Put the restaurant Market to Table in your GPS and park in the free three-story brick lot across the street, or Uber it to, say, Urban Flats. Once you’re on Plant Street, you’ll see a load of decent reasonably prices restaurants, a cute French bakery Rosalie with nice little meals, plus a few boutiques and other businesses. There’s a railroad museum and a history museum too (I’ve never been to either). It’s a nice place to walk around and hang out. You can just hang out on the wooden benches on the island in the middle of Plant Street. On Friday nights, an old-fashioned men’s quartet performs for free.

West Orange Trail – Scenic place to walk, rent bikes, rent rollerblades, job, meander, etc. You can start at either of the addresses below, then turn left or right. In nice weather, I like to rent a bike from WheelWorks (455 E. Plant St.) and ride in the most populated areas, which are between Killarney Station in Oakland and the Apopka-Vineland Outpost (5794 E. Apopka-Vineland Rd.). Both have bathrooms.

That One Spot – Great regular, veggie and vegan burgers, plus salmon and salads. Cheap. 10968 W Colonial Dr, Ocoee

Paloma – Coffee bar in downtown Windermere. 507 Main St, Windermere

Tru Nature Juice Bar – Smoothies and healthy foods. Far end of the same ugly strip mall as That One Spot. 10886 W Colonial Dr, Ocoee

LemonShark Poke – Great poke bowls. Dr. Phillips Marketplace. Excellent gelato at Carraia a few doors down. Not far from Trader Joe’s. 7600 Dr Phillips Blvd #102, Orlando

Farmacy – Organic produce and other foods. Winter Garden. 8 E Joiner St, Winter Garden

Rusteak – Not my fave, but it’s more chi-chi than anything else near here so people love it. Great happy hour menu for an affordable meal in a nice atmosphere. Ocoee

Pio Pio – My favorite restaurant in Ocoee. It’s Peruvian – (or maybe Colombian?) -style roasted chicken. I get the No. 2, a quarter chicken with a beautiful big salad and a garlicky dressing. I sub in plantains for fries, and I’m stuffed and happy. https://www.facebook.com/piopiomaguire/

Yellow Dog Eats – Casual funky restaurant with interesting salads and barbecue, often with live music on the patio. Choose the Gotha location.

Taste of Chengdu – It’s not in the neighborhood, but this place has great Chinese food.

Taste of Chengdu

Taste of Chengdu

Hawkers – Casual (loud; try to sit outside if it’s crowded) table-service restaurant featuring the street foods of seven Asian countries. You want the Windermere or Mills location, depending where you. Highlights: spicy curry laksa soup, roti canai flatbread with curry dip, udon noodles with chicken.

Bonsai – Small super-friendly spot for sushi and other raw-food Japanese dishes, plus shrimp dumplings and other small hot foods. The sushi and rice bowls with spicy mayo are fave. Not much in the way of hot entrees beyond (fried) katsu and tempura dishes.

Slate – Fashionable spot for a mix of foods. They go overboard trying to make simple things excellent, but the pizzas are great. Just do not order the avocado toast.

Urbain 40 – Kind of posh, kind of bistro-y, French and American, kind of special-occasion, with a 40s-ish jazz theme in the lounge. Big portions, so I usually just get an appetizer. It’s a nice atmosphere with a nice menu.

Pane d’Or – The only excellent bakery in this part of town. Freshly baked breads and pastries, owned by a very sweet couple.

That’s it. Get into the sunshine, grab yourself from culture and enjoy the Orlando we locals inhabit.